caribbean yacht holidays

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Find Caribbean Crewed Yachts for the Vacation of a Lifetime

The Caribbean is one of the most popular destinations for yacht charters in the world, featuring crystal-blue waters, white-sand beaches, and more than 5,000 islands and cays to explore. With so many islands to choose from, your Caribbean yacht charter itinerary can be tailored to your preferences, giving you the perfect opportunity to island-hop and explore everything the tropical islands have to offer while comfortably kicking back inside luxurious accommodations on the water.

On your private yacht charter , you will be able to explore lively harbors, secluded beaches, tropical rainforests, world-class dive sites, and much more. The possibilities are endless!

Caribbean Yacht Charter Highlights

• More than 5,000 islands and cays to explore
• A great winter destination
• Crystal-clear, sparkling blue waters
• Long stretches of white-sand beaches
• Luxury hotels, five-star restaurants, and spas
• Islands with their own unique cultures and cuisines
• A large selection of crewed yachts for charter

Showing 1–4 of 92 results

282.2ft / 84m

239.6ft / 71m

228.6ft / 68m

223.7ft / 67m

Caribbean Yachting Season

The Caribbean high season for yacht charters runs from mid-December to early May, with Christmas and New Year’s the most popular and busiest times of the year. But due to the islands’ locations near the equator, temperatures remain ideal throughout the year, making off-season charters just as enjoyable.

Keep in mind, however, that there is an increased chance for storms and hurricanes during the summer season, mainly from mid-August to mid-November. Most charter yachts leave the area during that time.

Caribbean Crewed Motor Yacht Charters

Remember When

162ft / 48m

Sweet Escape

130ft / 39m

116ft / 34m

Caribbean Catamaran Charters

105ft / 31m

Serenity Now

Caribbean Crewed Sailing Yacht Charters

Area Guide: Caribbean Charter Destinations

Are you ready to explore all that the Caribbean has to offer? There are three main island areas in the Caribbean, all fantastic destinations for Caribbean charter yacht vacations.

The Grenadines

The Grenadines are untouched by mass tourism and industry, and they are the perfect charter destination if you are looking for solitude and you enjoy exploring remote areas. A great combination of lush rain forests and sandy beaches awaits!

This is a great summer charter destination because the islands aren’t usually affected by hurricanes.

The Leeward Islands

Leeward Islands yacht rentals offer the perfect combination of luxury and solitude. You can visit the glitzy islands of St. Maarten and St. Barts one day and get lost in the remoteness and tranquility of Anguilla the next day.

These islands are rich in history and offer great restaurants, upscale resorts, and trendy harbors.

The Virgin Islands

The Virgin Islands are the perfect location for first-time charterers and families because of their calm waters, protected natural anchorages, and short distances between the islands.

The BVI are a great destination for a catamaran or sailing yacht charter. Caribbean locations here have constant yet mild trade winds year round, and the area offers fantastic diving and snorkeling.

Where Can I Charter a Yacht?

When you choose Worldwide Boat as your Caribbean yacht charter broker, we can help you charter a luxury boat anywhere in the Caribbean or anywhere else you’d like to go, from the Mediterranean to Alaska to the Galapagos Islands.

How Do I Book a Private Yacht?

The best Caribbean yacht charters can be booked in just a few easy steps:

• Choose our experienced yacht charter specialists to assist you through the process of booking a yacht.
• Search by destination or by boat, or use our advanced search tool to filter your options by the number of guests, yacht type, destination, and/or your budget.
• Pick the option that best fits your needs and your dream vacation.
• Reserve your yacht by signing a contract with the yacht owner.
• Enjoy your vacation!

How Much Does it Cost to Charter a Yacht in the Caribbean?

Weekly rates for Caribbean boat charters are dependent on a number of factors, including the type of yacht, the season, and your destination. Motor yachts, for example, typically range from $15,000 (yachts up to 80 feet) to $150,000 or more (yachts over 150 feet) per week.

During the Caribbean high season (Christmas, New Year’s, and January/February), yacht charter Caribbean prices tend to increase slightly. Areas with large charter fleets, like St. Martin, tend to have more competitive pricing than areas with smaller fleets.

How Much Does it Cost to Charter a Catamaran in the Caribbean?

Most catamarans offer all-inclusive rates, which start at $10,000 for catamarans under 50 feet and run up to $50,000 or more for catamarans of 80 feet or more. The Caribbean is an ideal destination for a catamaran charter, and across the region, you’ll find a variety of sailing and power cats available for charter.

Ultimately, the cost of a catamaran charter is dependent on the time you visit, where you go, local taxes, and the number of ports you visit. A luxury yacht charter in the Caribbean’s high season (New Year’s or Christmas) will cost significantly more than a catamaran charter in summer.

Can I Rent a Yacht for a Day?

Rates for yacht rentals are usually weekly, but when you talk to a Caribbean yacht charter broker at Worldwide Boat, we can look at your budget, plans, and interests to help you get the best experience possible.

Caribbean Yachting Hotspots

Caribbean sailing charters give you access to white-sand beaches and laid-back island vibes, but they can also offer action-packed itineraries. From island-hopping and hiking to snorkeling and cliff-jumping, adventure awaits on a Caribbean yacht charter!

Some of the region’s must-see destinations include:

• St. Martin : Known for its upscale eateries and amazing cuisine, as well as high-end spas, shopping and casinos, St. Martin is the yachting capital of the Caribbean. This island is part French and part Dutch, and it’s close to islands like St. Barts and Anguilla, making it a favorite jumping-off point for island-hopping adventures.
• St. Barts : St. Barts (sometimes called St. Barths) beckons A-listers to its posh beach clubs, fashionable shops, and five-star eateries. Visitors will find a collection of truly spectacular powdery beaches, Michelin-starred restaurants, and excellent shoreside amenities, all within cruising distance of St. Martin.
• Antigua : Antigua epitomizes the relaxation and bliss of the Caribbean. Known for its 365 beaches (one for every day of the year), the tiny island is a sailor’s dream, offering warm waters, steady winds, safe anchorages, and a lively regatta calendar.
• Grenada : Grenada is revered for its beautiful beaches, abundant marine wildlife, and vibrant cuisine (spiced with local nutmeg, mace, and allspice). Spend a day relaxing on Grand Anse Beach, which is consistently ranked one of the best in the world. Island-hop to neighboring isles like Petite Martinique, or spend a day snorkeling one of Grenada’s famous reefs.
• Anguilla : Anguilla is one of the most tranquil Leeward islands. Escape to Dream Bay or one of the numerous nearby coral cays for some supreme R&R. A diving and snorkeling mecca, Anguilla is home to some of the Caribbean’s best shipwreck dives. Plus, the island boasts a calendar of must-see festivals and events, including a jazz festival in November and Carnival in August.

Why Charter a Yacht in the Caribbean?

The best Caribbean yacht charters offer a bit of everything: Relaxation, sun-soaked beaches, delicious culinary treats, refreshing rum-infused cocktails, and calm waters for cruising. Here are some highlights:

The Inescapable Beauty of White-Sand Beaches

Caribbean beaches have almost a mythical quality to them. It’s no wonder explorers were once willing to board wooden ships and travel thousands of miles just to see them in person.

Every island offers a selection of untouched and charming beaches for you to explore. From one-of-a-kind places like “Pig Beach” in the Bahamas to the cosmopolitan Great Bay Beach in Philipsburg, St. Martin, the beaches across the Caribbean offer legendary sights and attractions.

Colorful Celebrations and Friendly Faces

The Caribbean is known for its parades, bars, nightclubs, and parties, not to mention world-famous cocktails. When you want to step off of your luxury yacht charter, Caribbean shores and islands offer a world of fun to immerse yourself in.

A few must-see events include the St. Barth’s Bucket (if you’re into superyacht racing), the annual Carnival celebration, and the St. Lucia Jazz & Arts Festival .

Amazing Wildlife and Adventure

If snorkeling in vibrant and colorful coral reefs, diving into underwater museums, or parasailing over clear waters are some of the items on your bucket list, you can certainly get it all done during your visit to the Caribbean.

You’ll find a variety of unique adventures, from the underwater sculpture park of the Grenadines to the natural seaside baths in Virgin Gorda and hiking the Pitons in St. Lucia. The Caribbean gives you to plenty of chances to get outside and enjoy yourself.

Nonstop Relaxation

Because the area is so close to the equator, the Caribbean offers warm weather to lounge in all year round. Feel pampered aboard a luxury crewed rental yacht, and then feel calm while sinking your toes into soft, powdery white sand. Enjoy the spas, rum cocktails, and quiet, isolated beaches: Charter guests can experience supreme relaxation in the Caribbean.

Book Your Caribbean Charter With Worldwide Boat

Discover the beauty of the Caribbean with a luxury crewed yacht charter. Contact a broker with Worldwide Boat today to learn more about available yachts and itineraries for the Caribbean.

Last edited by Katja Kukovic

Caribbean yachts by type

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Sailing Holidays in the Caribbean

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Luxury New Year Sailing in the Caribbean

• 29 December 2024, 8 days
• Vessel: Chronos
• Port: St Lucia, Caribbean
• Board type: Full Board
• 28 December 2025, 8 days

Embark on an unforgettable sailing holiday in the Caribbean and explore the breathtaking beauty of this tropical paradise. Our fully skippered Caribbean sailing holidays take you to some of the most stunning sailing grounds in the Caribbean, including St Lucia, St Vincent and the Grenadines, Antigua and Barbuda, and the British Virgin Islands. With the ever-present trade winds, year-round warm sunshine, and diverse selection of islands and cultures, you’ll soon see why the Caribbean is one of our favourite sailing destinations.

Skippered Sailing Holidays in the Caribbean

All our Caribbean sailing holidays are fully crewed, and you can choose from cabin charter or private boat charter options to suit your preference.  Step ashore from sheltered anchorages to experience true Caribbean culture; from small fishing villages to lively colourful carnivals and beautifully breathtaking hidden harbours tucked away under emerald green hills. Wander the islands, swim with sea turtles and while away your evenings under the stars eating mouth-wateringly tasty local cuisine freshly prepared by your onboard chef. Discover a more authentic side to these laid-back isles where warm hospitality and smiles are guaranteed.

Read our Top Ten reasons to take a sailing holiday in the Caribbean here!

Sustainable Sailing Holidays in the Caribbean

Those seeking a sustainable sailing holiday in the Caribbean will be spoilt for choice as a selection of our fleet all make the annual voyage across the Atlantic under sail. Guests can choose from a selection of vessels including  Chronos , Rhea , Florette , Grayhound and Eye of the Wind . Our vessels here largely operate under sail which enables our skippers to introduce guests to a more authentic Caribbean, unspoilt by mass-tourism and over-crowded beaches. Operating largely under sail also reduces the amount of carbon produced by our holidays, and all our vessels ensure to minimise their impact on the environment wherever possible.

Luxury Sailing Holidays in the Caribbean

For those looking to explore the Caribbean in luxury, join our yachts  Chronos , and Rhea to experience these magical islands in comfort. Indulge in the ultimate Caribbean adventure, enjoying 5-star cuisine on board, luxurious interiors with private ensuite cabins, and even on board water sports on some vessels. Immerse yourself in the beauty of the Caribbean islands whilst enjoying luxurious amenities and sailing in style.

Tall Ship Sailing Holidays in the Caribbean

If you’re searching for a unique adventure holiday in the Caribbean, step on board our traditional vessels Florette  and Eye of the Wind . Enjoy an active tall ship sailing holiday in the Caribbean, and experience authentic, hands-on, traditional sailing in an area with some of the richest maritime history in the world.  A sense of adventure is a must on these vessels, as you venture off the beaten track and explore the hidden coves of the Caribbean islands. If you’re not an experienced sailor there is no expectation to get involved, but the friendly crew encourage guests to take part in sail hoisting, navigation and even taking the helm!

Wildlife in the Caribbean

The beauty of the Caribbean doesn’t just lure us humans, the waters here teem with wildlife and a sailing holiday provides the best way to spy some of its marine inhabitants. Keen eyes will be rewarded with graceful sea turtles gliding effortlessly through the water, playful Bottlenose Dolphins swimming with the wake of the bow, humpback whales who visit the warm waters to breed as well as a variety of rays and colourful tropical fish. Iguanas scuttle along the shoreline whilst starfish, coral, conch’s and a plethora of crustaceans, shellfish and other marine life can all be discovered by those who look. Each of our vessels sail with snorkels and masks so take the opportunity to slip into these bath-like waters and watch the busy underwater world in action, you won’t be disappointed.

Caribbean Cuisine

Caribbean cuisine is as colourful and varied as the islands with distinct flavours reflecting their rich cultural history. Fusing together West African, Creole, Cajun, Amerindian, European, Latin American, Indian/South Asian, Middle Eastern, and Chinese (phew!) we guarantee dishes to set the tastebuds tingling. Our onboard chefs will prepare your meals each day using locally sourced produce wherever possible. Sample island-grown plaintains, sweet potatoes, cassava, chickpeas, bell peppers and coriander along with freshly caught fish and seafood. Bright, colourful mouth-watering dishes packed with eclectic flavours served alfresco, the perfect accompaniment to a sailing holiday in the Caribbean.

If you have any dietary preferences or intolerances, please do advise us prior to travel so we can advise the boat in advance.

Read more about our sailing holidays in the Caribbean

For a more in-depth guide on the highlights of a sailing holiday in the Caribbean, head to our Journal where you can find a guide to sailing in Grenada , St Vincent and the Grenadines , and the British Virgin Islands .

Destinations

Our range of vessels enables us to offer several destinations all over the globe. Which adventure will you choose?

With vessels of all sizes and each with a unique history and construction, there is no shortage of choice for your sailing holiday.

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CARIBBEAN YACHT CHARTERS

1272 boats available for bareboat or crewed charter

Yachts from professional fleet operators in Caribbean

Free cancellation of reservation without obligations within 4 days

Most popular boats For rent in CARIBBEAN

Fountaine Pajot Elba 45 - 4 + 1 cab. catamaran charter (2024)

Rent a boat Leopard 45 (2023) in St Martin

Catamaran Fountaine Pajot Aura 51 (2022) for rent in St Vincent and the Grenadines

Oceanis 41.1 sailboat charter (2019)

Rent a boat Voyage 440 (2006) in Cuba

Catamaran Lagoon 40 - 3 + 2 cab (2020) for rent in Bahamas

Dufour 470 - 3 cab. sailboat charter (2022)

Rent a boat Lagoon 46 - 4 + 2 cab. (2023) in USVI / US Virgin Islands

Sailboat Dufour 470 - 3 cab. (2023) for rent in USVI / US Virgin Islands

Oceanis 42 sailboat charter (2019)

Top destinations in caribbean for boat rental.

484 boats for charter

from €1,096 per week

251 boats for charter

from €1,214 per week

THE BAHAMAS

144 boats for charter

from €1,689 per week

US VIRGIN ISLANDS (USVI)

118 boats for charter

from €1,693 per week

99 boats for charter

from €1,350 per week

78 boats for charter

from €1,368 per week

• Guadeloupe 68 boats in Guadeloupe 68
• Antigua 48 boats in Antigua 48
• St. Vincent 31 boats in St. Vincent 31
• St. Lucia 27 boats in St. Lucia 27
• Puerto Rico 6 boats in Puerto Rico 6

Types of boats available for rent in Caribbean

Catamaran charter

975 catamarans available for rent in Caribbean, form €1,229 for 1 week charter. Ideal option for group of friends or family vacation.

Sailboat charter

There are 228 sailboats available for charter in Caribbean, prices start from €1,096 per week. Most budget friendly option for a vacation.

Power boat charter

44 powerboats available in Caribbean for rent, starting from €1,729 per week. Bareboat or crewed options available for sailing vacations.

Trimaran charter

11 trimarans available for rent in Caribbean, with prices from €3,133 per week. Great option for skippers looking for performance boats.

Gulets charter

Currently not available for charter in this country. Check other boat types.

Houseboat charter

Yacht charter types available in Caribbean

Bareboat charter, crewed yachts, by the cabin charter, skippered boats, cost of boat rental in caribbean.

Average yacht charter cost in Caribbean starts from €1,096 per week. Graphic below represents fluctuation of charter prices in Caribbean during the year, based on a sample of 50 boats ranging from 40 to 50-foot. This graphic shows months with lowest prices during the year as well high season when prices are above average. Before booking the boat at lowest rate, please check sailing conditions as usually best prices are during off season.

Caribbean Yacht Charter Reviews with 12knots

United States

“My first experience with 12 Knots”

My first experience with 12 Knots, very good services, very good communication skills, prompt reaction and easy procedure for booking. I highly recommend their services. Clearly, not everybody could be satisfied, but personally I did not find any wea…

Flori Grottoli

“Spanish Virgin Islands are stunning / March 2019 / Puerto Rico / Dufour 412”

The experience was beautiful and the Spanish Virgin Islands are stunning! Even though we started off with a few setbacks (had to switch boats because of technical issues), the marina made good and was very accommodating....they did the very best they…

South Africa

“Thank you Irina and the 12 Knots team”

Thank you Irina and your entire team for your excellent service culminating in a wonderful sailing holiday out of Fethiye, Turkey. The team at the Fethiye base was on top of their game and accommodating in every respect. The boat was in excellent con…

“Great company that provides great…”

Great company that provides great customer service and find the best deals. I'm especially grateful to Grigory for helping us negotiate and reschedule our multi boat sailing trip that had to be postponed because of COVID-19. Great job and thank you!

Adrian Grigorof

“Everything was arranged as planned”

We chartered 2 sailing catamarans for a 10 day USVI/BVI vacation and everything was arranged as planned. Good communication, good service, no surprises. The boats were in perfect shape and we had a great time.

Gerzsenyi Andras

“The boat was in super condition”

The charter was excellent, everything perfect. The boat was in super condition (brand new), and very clean. The staff was helpful, and very kind. We enjoyed the trip very much and are looking forward to our next booking.

Sailing Around Windward and Leeward Islands of the Caribbean

The  Caribbean covers a huge region of widely spread islands 2,000 miles (3,218 km) long.

The larger ones have become sovereign countries with broad range of amenities for sailors, while the smaller ones still preserve its untouched rural charm and tranquility.

From the western tip of Cuba to the Leewards in the east, then south to the top of South America and along Venezuela’s north coast – this chain of islands has created a hook-like shape around the Caribbean Sea. Location like this is always an enticing bait for sailing - perfect climate and  array of diverse cultures, customs, cuisines and experiences, water sports and an unlimited number of other attractions.

Planning sailing vacations in Caribbean, you may wish to consider these groupings of the islands as points of your itinerary, as they contain many popular cruising areas and harbor stops. There is no doubt that in the scope of Caribbean bareboat or skippered yacht charters  both groups have their charms and countless reasons to explore, which definitely makes it a great sailing destination.

Caribbean yacht rentals

12 Knots offers eleven yacht charter bases in the Caribbean region, each with unique individual character, providing sailing experience for everyone, from a novice to an experienced sailor. This region comprises more than 700 hundred islands and islets, so you can choose Caribbean sailing vacations with shot and easy hops or more challenging passages.

Taking Caribbean sailing vacations, you will find warm and steady trade winds in picturesque surroundings; discover plenty of great bars and authentic cuisine!

It’s up to you, choosing between the Leeward Caribbean islands with short and easy hops with line-of-sight sailing and the Windward with more challenging open water passages. Wherever you go, you will return home relaxed, refreshed and ready to start planning your next Caribbean sailing adventure.

The Windward islands

Windward Islands located at the southern end of the Caribbean island chain and stretch for over 300 miles to the south-eastern end of the Caribbean Sea. The Windward Islands are simply called so due to their position as they are exposed to the northeast trade winds. For experienced sailors, it can be right choice to sail among the four main islands: Martinique, St. Lucia, St. Vincent and Grenada. They lay far apart each other allowing open ocean sailing and while steady easterly trade winds, make passages north or south easy. With constant 12 to 25 knots wind, Caribbean sailing is among best in the world. Night anchorages in peaceful and protected areas give sailors freedom to explore and soak up British and French island culture. The islands of St. Lucia, St. Vincent and Grenada  were British colonies until they gained independence during the 1970s. Martinique is still an overseas department of France.

The climate of the Windward Islands is definitely a marine one.

When tropical heat reaches its peak, steady trade winds and daily sea breezes come to rescue.

Typically, dry and wet seasons go hand in hand here. Although the priority of more rainfalls is given to the eastern side of the islands mainly due to the prevailing north-east trade winds there.

The islands east of Puerto Rico were called “Windward Islands” by the Spanish, while the islands south of Puerto Rico were named as “Leewards “. And Dominica positions itself right on the border line between the Windward and the Leeward Islands.

Long time ago some of the islands used to be French colonies, subsequently gained its name as The French Antilles.

The population of the Windward Islands is mostly of African origin, with some exceptions of Chinese and Caucasians. The present day Windward Islands will welcome tourists with upscale resorts, stunning beaches and pleasant sunny weather.

After cruising through the Windward Islands, you may wish to set sails to the Leeward Islands.

The Leeward islands

The Leeward islands are located on the eastern edge of the Caribbean Sea and form the northeastern boundary between Caribbean and Atlantic Ocean, extending from Puerto Rico to the Windward Islands, forming part of the Lesser Antilles chain.

Although 700 miles long stretch of these magnificent isles mostly constitute the whole body of the Leewards, it provides the abundance of enjoyment: quaint fishing spots, ancient ruins and delicious authentic cuisine.

Blessed with balmy temperatures all around the year, The Leeward Islands are called leeward because they're away from the wind or downwind (in the "lee"). Leeward group of Caribbean islands includes: the U.S. Virgin Islands, the British Virgin Islands, Anguilla, Saint Martin, Saint-Barthelemy, Saba, Sint Eustatius, Saint Kitts, Nevis, Barbuda, Antiqua, Redonda, Montserrat and Guadeloupe.

One of two "sister islands", St Kitts and Nevis, provides a brilliant Caribbean experience, from their picture-perfect beaches and volcanic mountains to friendly locals and layers of history to explore. For the water sport lovers, there are numerous aquatic activities that include fishing, diving, windsurfing and surfing.

St.Kitts and Nevis

Switch from sailing to inland for a change and St.Kitts and Nevis will deliver the most exceptional hiking in the Caribbean. The dormant volcano of Mount Liamuiga is considered to be the toughest to climb. And with the experienced guide you may even try to descend in its crater!

The unspoiled landscape of dry littoral forest and rainforest will present memorable show of fauna and flora. Many plants are of culinary and medical use, and some even used in black magic, as informative guides would point out its botanical value.

The wild life-lovers will not be disappointed with variety of different types of exotic animals.

Actually, the Great Salt Pond has become famous for its largest habitat of green velvet monkeys.

St. Kitts and Nevis will keep you captivated with majestic view of huge conical shells, remains of old sugar mills, along with some other plantation ruins, built in the 18 th century.

Back to water activities, and tourists will be pleased with what these two island can offer: deep-water fishing, snorkeling, scuba diving and more.

Then in order to satisfy your growing appetite visit two popular restaurants: Carambola and the Shipwreck Bar and Grill to enjoy its delicious local meals.

A yacht charter in the Caribbean Leeward Islands offers sailors an unrivalled remarkable experience. Enjoy tropical landscapes, pristine palm-lined beaches and azure waters — all the joys of marine life.

Sailing over the Leeward Islands may have all the pleasures to offer: the Tropical rainforests, glittering coral reefs, and luxury sand beaches. That’s probably why most of the known tourist resorts on these islands play a critical role in their economy, as do banking and fishing. Many of them also rely on their status as a tax haven to promote offshore financial services as a source of government revenue. But there is much more to discover in the Leeward Islands. These Caribbean islands provide great variety of yachts for charter and pleasant sailing vacations. Most of the Leeward Islands are located close to each other with moderate winds from 10 to 15 knots and rather low wavers. BVI is the most popular area for Caribbean charters either bareboat or luxury crewed vacations. This is the right place for the novice sailor’s easy passages in line-of-sight sailing.

The climate of the Caribbean Leeward Islands can be described as tropical, but much drier than in Windward Islands. Though the climate does vary from island to island and can even be different in different parts of the same island. Rainfall increases with elevation and in more southerly latitudes. In some cases trade winds look like refreshing tonic to the tropical heat. There is minor seasonal variation, although the second half of the year, the wet season, is slightly warmer and rainier. The best time for sailing in the Caribbean may be the first half of the year. At this time the temperatures usually range between 81°F (27°C) and 95°F(35°C). Annual rainfall averages about 40 to 50 inches (1016 to 1270 mm). Keep in mind, that nearly every island had been severely damaged by hurricane activity in its recent history.

English is the most widespread language all around the islands, plus many of the people speak French and Dutch on the St Martin Island. Both English-based and French-based Creole are also spoken. The prevailing currency is The East Caribbean dollar. But St Martin is odd man out again, circulating the Netherlands Antilles guilder in the Dutch area and the Euro in the French region. Nevertheless, the US dollar is widely accepted throughout the islands.

If you eager to take part in sporting activities, then you may be pleased to know that cricket is widely played and followed in the former British territories. Besides, as in the rest of the Caribbean, music is also always a big part of local life. Enjoy the magical sounds of calypso, soca, steelpan, reggae, salsa and jazz — all of the mentioned has their adherents.

During your Caribbean yacht charter, you may wish to participate in some major holiday celebrations, including the St Kitts Christmas, New Year carnaval, the annual music festival, as well as Anguilla’s Emancipation Day and Culturama festival on August 1st.

The culture of the Leeward Islands is varied by different influences, including French, Dutch and West Indian. Due to that sailing around the Leeward Islands provides a wonderful choice of cuisine and some great restaurants to satisfy your affection for the finest dishes. By the way, the island of Anguilla offers true gastronomic feasts. When sailing in the Caribbean Leeward Islands, be sure to try freshly caught lobsters with a glass of wine.

Sailing the Caribbean With 12 Knots

So, while planning a Caribbean charter it is highly recommended to decide on how many islands you would like to visit in a given time frame. Research Caribbean boat rentals and determine which island you would like to have as a starting base. Then you can plan an itinerary for the week or ten days, taking into consideration distances between the islands and activities you would like to have, like island tracking, scuba diving, snorkeling, volcano hiking, or even shopping.

12 Knots team will give you plenty of useful information not only on the bareboat charter in Caribbean, but also itineraries, places of interest and peculiarities of each island.

Taking a yacht charter in the Caribbean is just a perfect combination of sailing and relaxation, authentic culture and a range of water sport activities. In a few words, this area may always offer something for everyone in these amazing islands’ surrounding.

Frequently Asked Questions about yachting in Caribbean

How much does it cost to rent a yacht in caribbean , how many boats are available for rent in caribbean , what are the main yacht charter bases in caribbean , what boats are available for charter in caribbean .

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Caribbean yacht charters - one resource for every luxury charter yacht

The proven resource for crewed yacht charter in the caribbean.

From the moment you contact us, you will be helped by an experienced and knowledgeable specialist who will take the time to understand your unique needs and preferences for your caribbean vacation. They will be your dedicated specialist and our exceptional personal service will answer every question.

The largest choice of crewed Caribbean yachts?

Absolutely, with our relationships built over decades we truly do have access to EVERY crewed private charter yacht based in, or visiting, every part of the Caribbean.

Whatever the type of yacht for your Caribbean charter, your vacation budget, or the size of your party, our specialists will guide you in choosing the ideal yacht for your Caribbean charter. It's your vacation to explore the islands the very best way possible - on a Caribbean charter yacht.

Browse different types of Charter Yachts in the Caribbean

Motor Yachts

This category of Caribbean yachts include mega yachts, super yachts, and all sizes of power yachts. With the maximum space for guests, both inside and out, these types of yachts offer excellent vacations. You can choose from a fast, agile yacht, one that is high-end and luxurious, a yacht with a classic design, or one that is contemporary. This is one of the many choices you’ll have when you plan your vacation. See some yachts:-

Crewed Catamarans are very popular in the Caribbean , especially in the BVIs. Catamarans offer ample deck space that allows everyone to relax together during their charter, sharing the same views throughout the voyage. Caribbean catamarans can typically accommodate between 6 and 12 guests. See some yachts:-

Sailing Yachts

If you are looking for a winter getaway, there is no better place to charter a sailing yacht than the Caribbean! Feel the warm, tropical breeze on your face. Experience the exhilaration as the wind fills the sails and the yacht is suddenly moved along by just the wind. Savor the magnificent beauty of the Caribbean as you sail silently from one island to the next. Although typically offering smaller spaces for guests, sailboats deliver a truly unique caribbean charter vacations . See some yachts:-

Sample Charter Yachts in the Caribbean

ODYSSEA. The 59' sailing catamaran Odyssea is ready to take you and your guests on your next adventure. Throughout she offers relaxing areas to lounge and enjoy the voyage, while enjoying the company of others or absorbing the serenity of the sea. Her spacious cockpit area offers large dining table, sun pad across the back, and wet bar. See ODYSSEA :-

OKTO. Get ready for adventure when you step on board the 217' mega yacht Okto. You and your guests will find plenty to do, as she offers plentiful spaces for lying out to enjoy the sun, enjoying a movie in the circular cinema, working out in the indoor gym with an amazing view, or enjoying the on deck Jacuzzi. See OKTO :-

NAMASTE. The immaculately maintained mega yacht Namaste offers 121 feet of opulence at sea. She features five well-appointed cabins, both a main salon and sky lounge, sundeck with Jacuzzi, gym equipment, and a long list of watersports including jet skis, wakeboard, fishing gear, and the list goes on. See NAMASTE:-

LIQUID SKY. The 67' sailing catamaran Liquid Sky was launched in 2024 by Fountaine Pajot. With four cabins, she accommodates as many as eight guests, and offers a number of places for you to hang out and enjoy the journey, including on the bow soaking in the in deck Jacuzzi, up on the flybridge taking in the views, or on the aft deck with al fresco dining. See LIQUID SKY:-

MARIAH PRINCESS III. The 77' Lagoon built sailing cat Mariah Princess III was built in 2020. She offers two queen cabins and two king cabins, all en-suite. The master cabin has a private deck, the flybridge offers an on deck Jacuzzi, and she has a generous complement of watersports, including onboard SCUBA. See MARIAH PRINCESS III:-

TRUE STORY. The 67' sailing catamaran True Story is ready to give you and your guests a fun and exciting charter in the beautiful waters of the Caribbean. She offers a spacious main salon, large cockpit with al fresco dining and lounge, and flybridge with conversational area. You and your guests can also enjoy a long list of water toys throughout your journey. See TRUE STORY:-

The British Virgin Islands include Tortola, Jost Van Dyke, Virgin Gorda, and more. There’s no better way to experience the waters and beaches of the BVI's than on a private Caribbean charter with a full crew to pamper you. Of all the islands in the Caribbean, the Virgins are furthest north. This makes them very convenient due to the proximity to San Juan and due to their direct flights from the United States. Catamaran sailing vacations and crewed sailing charters are very popular in the islands, and their protected waters make them a favorite spot for guests that are taking their first private Caribbean yacht charter. To learn more about them:

The U.S. Virgin Islands consist mainly of the three large islands of St. Thomas, St. Croix, and St. John. With lovely bays, long beaches, lush nature preserves, fabulous diving spots, and excellent, onshore evening entertainment, many choose to vacation in the USVI’s. Caribbean charters often visit both the BVI’s and USVI’s during the same week, as they are close to one another and the waters are generally calmer than in other parts of the Caribbean. They in general are also home to the largest fleet of crewed, all-inclusive, luxury catamarans. To find out more about them:

The Leewards are situated in the middle of the Caribbean Island chain. The major airports are located on St. Maarten and Antigua. Due to the English, Dutch, and French influences everywhere you look, they exhibit the best example of cultural sophistication anywhere within the Caribbean. If you are looking to see where the rich and famous go on vacation, you will want to visit the island of St. Barts; for many this is a must stop for a Caribbean yacht charter. Many mega yachts are available for rental in St. Maarten, as it has become a popular mega yacht Caribbean base for the winter. To learn more about the Leewards:

The Grenadines are also called The Windward Islands. Oftentimes our guests will choose a sailing charter over a motor yacht when in the Grenadines, due to the more constant tropical breezes that occur. The islands are much less developed than the rest of the Caribbean, and the inhabitants live on their own time schedule, which enhances the feeling of getting away. The northern most island accessible by air is ST. Vincent, while the southern tip’s major airport is on Grenada. There are fewer Caribbean charter yachts based here; however, occasionally some charter yachts are happy to relocate in order to offer a vacation that happens a little off the beaten path. To find out more about the Grenadines:

What Type of Charter Yacht?

There are all types of Caribbean yacht charters available, including mega yachts, power yachts, catamarans, and sailboats. We have helped countless clients choose the right charter yacht, learning what features and amenities make a difference on caribbean charter yachts. Learn more about different types of Caribbean yachts.

Where Can You Go?

Typically you’ll choose between the Virgins, Leewards, and the Grenadines to charter your yacht. Beyond the region, it is your Caribbean to explore. It’s important for you to remember that there is no cruise ship itinerary to worry about! Your itinerary will be custom designed specifically for you, with you, and is flexible to changes during your charter. We have put together some samples for you to get an idea of what you might like to do while on vacation in the Caribbean. Interested in seeing a sample cruise itinerary ?

Find Your Perfect Yacht for a Caribbean yacht charter

To see the Caribbean yachts we have in our online database, please select a yacht type and your budget below. Please keep in mind that we do not have every available yacht online. There are many more yachts available for you to choose from when you contact one of our specialists.

For your personalized selection including yachts not online:- Email us now

Caribbean Charters - When To Go.

One of the lovely things about the Caribbean is that the temperatures remain consistent throughout the year; however, there are some other weather considerations that you will want to factor in when making your caribbean yachting vacation plans. Read More....

Vacations here are most popular between November and July.

If you are thinking of a megayacht, you will want to keep in mind that many of these private yachts which are Caribbean based in winter leave in the late spring and early summer months. They will return again in early winter; however, this does limit their availability. To charter a mega yacht, you will want to make sure that you do so well in advance.

Motor, sail, or catamaran yachts, on the other hand, often have selections available year round. Holidays like Christmas, New Year’s, and Easter do need to be planned for as early as possible as these are very popular charter times.

The availability for Caribbean charters can also be affected by the weather in other climates, for instance, when the severity of the weather is bad in the United States or Europe, especially between January and February, the charters are often booked. This is due to many clients looking for a break from the cold.

What Do Our Clients Say About The Caribbean?

Are you excited yet? You should be! Our clients have enjoyed fantastic Caribbean vacations. There is an endless number of places to visit in the Caribbean, from smaller islands to absolutely must be seen locations like St. Barts. Read some of our Caribbean charter reviews from clients who booked a Caribbean charter with us.

Ready to learn more about Caribbean charters?

We are specialists who will make your trip a reflection of our expertise! We know clients need to be confident in their charter vacation plans, so we encourage our clients to benefit from the knowledge base we’ve been building for years. You’ll speak to an authority on Caribbean charters without any obligation on your end.

Test our expertise with your questions!

Contact a specialist - available 7 days a week.

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Do you have a particular yacht in mind? We likely have it online and if not, email or call us for details. Search for it online by name here:

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Caribbean Sailing Charters

This stunning cruising ground is everything you would imagine and so much more. In the British Virgin Islands (BVIs), Caribbean sailing yacht charter guests can spend their days snorkelling vibrant coral reefs before visiting the famous Soggy Dollar Bar - known for its intoxicating Painkiller cocktail - for a night you’ll never forget.

Caribbean sailing charters.

A sailing holiday in the Windward Islands makes for a bounty of wild experiences; allow the scent of exotic spice to enchant you as splash in Grenada’s crystal-clear waters, or discover real island living in Barbados.

In the Leeward Islands, St Kitts promises rugged adventure while  Caribbean sailing holidays  to Antigua offer a chic escape complete with Michelin-Star cuisine. The unspoiled Grenadines are the place to come if you seek undisturbed relaxation, the most untouched of all the Caribbean island groups.

Oyster offers sailing yacht charters exploring every one of these blissful regions. Read on to learn more.

CRUISING GUIDE: CARIBBEAN SAILING YACHT CHARTERS

The best time to visit the Caribbean by sailing yacht charter is between December and April. Although the region is known for having a permanently glorious climate, averaging between 24-29°C/75.2-84.2°F all year round, a visit during these months offers lower humidity and less chance of rainfall. It also falls outside of the June-November hurricane season. You can expect temperatures of around 26°C/78.8°F and blissfully calm waters, perfect for bathing away your troubles or getting your heart racing with some exhilarating watersports.

Some of the most popular times for crewed Caribbean sailing yacht charters include the Christmas and New Year’s period and the Easter weekend when the islands fill up with festivities. You will discover more secluded sailing destinations and deserted beaches outside of these peak holidays, but the festive magic is hard to beat. The choice is yours...

Maximising your island-hopping experience onboard a Carribean sailing yacht charter allows you to explore every little bay that takes your fancy. Drop anchor by tiny secluded coves and discover deserted islands where you really can get away from it all.

For skippered Caribbean sailing holidays, look no further than Oyster. Our beautiful boats are light and spacious with luxurious furnishings that prioritise comfort without compromising on practicality. Large windows below decks mean you’ll be able to spot every single palm tree that dots the horizon, while our highly-professional crew come equipped with a local’s knowledge of every part of the Caribbean.

Explore this stunning region on one of our  luxury sailing yachts , or read on to learn about sailing the beautiful island groups of the Caribbean.

Sailing in the British Virgin Islands

An iconic cruising ground for Carribean sailing holidays, the BVIs are not to be missed. With nightlife that will have you dancing until dawn, seafood restaurants with fresh tuna and gin-clear waters offering perfect conditions for snorkelling and diving, this is the epitome of island living. Sail out to the caves at Norman Island to swim amongst exotic sea life and marvel at the vibrant colours. For charter guests who want nothing more than to lie on the sand and relax, cruise over to Anguilla, where the island’s flat topography makes for some truly phenomenal beaches. As the sun begins to set, head to The Rum Bar at Cooper Island, or for those who want to party all night, why not hop between the many lively bars on Jost Van Dyke.

The BVIs provide a delightful climate throughout the peak charter season: a perfect escape from the colder weather of the Northern Hemisphere.

Sailing in the Windward Islands

The Windward Islands deliver surprise after surprise on any Carribean sailing holiday, with each island full of its own unique character. St Lucia promises a vibrant history and rugged landscape - hike the Pitons for some truly incredible views across the islands and out to sea. Bequia is considered by some as the perfect Caribbean island, its difficult to get to by aeroplane meaning it has been protected from mass tourism, preserving all of its natural beauty. Glamourous Mustique is the favourite holiday spot of A-List celebrities and supermodels. However, despite its famous visitors, this three-mile haven is surprisingly low-key, with only one (extremely elegant) hotel on the island.

Authentic Caribbean living and jaw-dropping natural beauty await in the Grenadines - a 35-island region that lies within the Windwards. Snorkel in the Tobago Cays to meet friendly marine turtles and revel in the untouched landscape. Head to Mayreau for the wild nightlife and swim at best-kept-secret beach Salt Whistle Bay. Try your hand at kiteboarding on Union Island, and hang out with the locals in this laid-back set of villages. Caribbean sailing yacht charterers will love the variety of experiences that await in this cruising ground.

Head to the Windward Islands from December through to April to experience them at their best, with a multitude of fantastic events across all the islands. Look out for the Barbados Film Festival, now in its third edition and normally held in late January, or the lively Carriacou Carnival in mid-February. Also, visit in February to experience the yearly St. Vincent Yacht Club Regatta, or in March for the Saint Vincent’s Blues and Rhythms Festival.

Sailing in the Leeward islands

The Leeward Islands are famous for their good sailing winds, making them a must-visit destination for experienced sailors or those on skippered Caribbean sailing holidays, where the crew will guide your vessel while you simply relax. Head to Antigua, one of the most important superyacht hubs in the Caribbean, for unmatched glamour and a rich history. Don’t leave without touring Nelson’s Dockyard, the preserved 18th-century base of the British Fleet in the West Indies.

As the smallest landmass ever to be divided between two nations, St Martin/St Maarten offers a chance to experience both French and Dutch culture while revelling in the island’s majestic green peaks and crystal-clear waters. Heavenly St Barts has not one but fourteen gorgeous beaches at which to stretch out and do nothing or to get your pulse racing with some exhilarating water sports. Meanwhile, on St Kitts and Nevis, lose yourself in sugar plantation history at the UNESCO-protected Brimstone Hill Fortress National Park. This is an island group for those with an adventurous spirit, but it wouldn’t be a Caribbean sailing yacht charter destination without also being packed full of amazing beaches upon which you can soak up the sun.

In peak sailing season, the Leeward Islands offer the lowest humidity of all the Caribbean islands - perfect for keeping cool during those more challenging hikes - and temperatures average between 27°C/81°F and 35°C/95°F, ideal for lazy days on the beach.

Learn more about how to charter a sailing yacht in the Caribbean with Oyster. Discover  Oyster luxury sailing yachts for charter  or contact Oyster Charter Manager, Fiona McCarthy to begin planning your trip.

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Winner of European Yacht of the Year 2023. She sets a new 50 foot bluewater benchmark, offering a stunning combination of sailing performance, comfort, safety and luxurious living space.

Heralding a new generation of Oysters, this 60 foot bluewater cruiser is a sailing yacht for all oceans. Practical and well-provisioned for long distance sailing or cruising in coastal waters.

The much-anticipated Oyster 595 is well-proportioned and extremely versatile. Offering exciting, customised build options with no compromise, she is capable of great things.

A versatile sub-70 foot sailboat offering the perfect balance of size and practicality. She can be sailed shorthanded effortlessly or take a full crew and up to eight friends and family.

This long range 75 foot cruising yacht is designed for very big adventures. A joy to sail yourself, she also boasts dedicated crew quarters.

Oyster 885SII

An exhilarating 90 foot sailing yacht, delivering comfort and safety with uncompromising performance. She is capable of taking you anywhere in the world effortlessly, in luxury and style.

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ALL-INCLUSIVE SAILING HOLIDAYS IN THE CARIBBEAN

Sailing in the Caribbean is a real joy! Stunning scenery, delightful anchorages, and amazing weather: enjoy some of the most beautiful islands on earth.

From £2950 per person.

View our Caribbean brochure

We take you to the Caribbean that is hidden from you on a normal beach hotel holiday! Explore bays and coves that tourists cannot reach; the forest-clad mountains of Grenada; the exclusive glamour of Mustique; the film location for Pirates of the Caribbean in the Tobago Cays; and the excitement of trade-wind sailing around the idyllic Grenadine islands. Feel the warm wind fill the sails, swim with turtles, snorkel the reefs, watch the sun set from a beach bar – every day! Your dreams become your memories.

Come as a couple, individual or group of friends and family and experience this adventure. Sailing holidays used to be only for big groups: not any more! Meet discerning, like-minded people in the safe, comfortable environment of your luxury yacht on a shared or private charter. Make new friends while discovering wonderful new places together.

Discover the Caribbean that cruise ships and package tours cannot reach, a tropical paradise of deserted beaches, lush islands and refreshing seas. The moment you step aboard, the rhythm of the islands takes over. Days are marked by sunrises and sunsets: how much or how little happens in between is completely up to you!

It’s all included

From £2950 per person

• Luxury, modern catamaran with plenty of space to relax
• Private en-suite cabin
• Experienced skipper and crew with a wealth of local knowledge
• All meals included and freshly prepared
• Every other night we take you to a restaurant ashore
• We cater for special dietary requirements
• All drinks on board and in restaurants
• Return transfers to the airport
• All cruising taxes, customs and immigration fees
• Yacht fuel, moorings, laundry, bedding, towels, water and ice
• Vessel insurance
• No credit card fees

Your skippered yacht sailing holiday

We take you to the Caribbean that is hidden from you on a normal beach hotel holiday! Explore bays and coves that tourists cannot reach; the forest-clad mountains of Grenada; the exclusive glamour of Mustique; the film location for Pirates of the Caribbean in the Tobago Cays; and the excitement of trade-wind sailing around the idyllic Grenadine islands. Feel the warm wind fill the sails, swim with turtles, snorkel the reefs, watch the sun set from a beach bar – every day! Your dreams become your memories.

On-board luxury and comfort

There’s something wonderfully hypnotic about sitting on deck and watching the landscape drift slowly by. It’s one of the best things about travelling by boat. There’s also no hassle of packing and re-packing. Our itineraries allow you to explore new places every day: dots on a map that often can’t be seen any other way! There’s always the kick of waking up in your cabin and wondering what new heart-stopping views await you today!

Delight in the journey and in every detail along the way. With Escape Yachting, you’ll experience all-inclusive personalised service at every turn. New experiences are accompanied by warm smiles and prompt attention. Never in the way yet never out of reach, our gracious award-winning service makes your sailing holiday remarkable in every way! It’s all about the little touches with Escape. Your friendly crew, including a qualified professional skipper, have years of experience and useful local knowledge from sailing in the Caribbean and act as your guide, steward and chef. Who wants to be doing the cooking and washing up while they’re on holiday? You’ve earned the right to relax and spend time with each other, enjoying yourself while we take care of all that for you.

Escape to the sun with family and friends!

Whilst we love sailing in England, we also enjoy discovering sunnier climes by yacht, especially in the winter! Escape Yachting have sailed with guests around the Ionian Islands in Greece, on an adventurous expedition in Desolation Sound out of Vancouver in Canada, exploring the Dalmatian coastline of Croatia and sailing the tropical waters of South East Asia as well as returning to the glamorous Caribbean every winter.

Our full-service approach extends to all the fiddly arrangements of international sailing. We take care of everything for you, so all you have to do is sit back and enjoy your holiday.

Contact us today and let us help you organise your Caribbean holiday.

“I felt like I got a superyacht experience for the price of a cruise. Every detail was considered and everything was included; the itinerary had the perfect balance of action and relaxation. For an incredible (and unique) Caribbean holiday I would definitely recommend Escape Yachting.” Adam

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Caribbean Yacht Charter

The Caribbean Sea offers more than 700 islands to choose from and to sail around during your next Caribbean boat charters experience. Sailing the Caribbean caters to all tastes.

Explore the finest white sandy beaches and hidden coves, the most transparent blue waters on the Caribbean boats that make feel you more comfortable.

A Caribbean boat charter always reserves you to enjoy a 5 stars resort atmosphere, while also being able to enjoy and deeply explore the nature and secrets of the various islands in the area. Every paradisiac island, atoll, and beach of the Caribbean is an excellent option, wherever you will sail, the Caribbean will reserve you your lifetime yacht charter.

You can choose to cruise in the enchanting British Virgin Islands , embarking in Tortola, or to hire a yacht in the Windward Islands , better known as Dominica, St Lucia , Grenada, St Vincent, and the Grenadines and Martinique . Sailing west you will encounter the fascinating Cayman Islands , close to Jamaica and Cuba , where you join Havana or Cienfuegos. While the southern and eastern coasts of Antigua and the striking Barbuda are enclosed by corals, ensuring ideal conditions for shallow diving and extraordinary snorkeling. The same coral reefs that once wrecked ships, now attract snorkelers and scuba divers from all over the world. And separated by just a few miles off the coast, Barbuda 's fascinating little island.

MOTOR YACHT RENTAL CARIBBEAN

The most luxurious and extraordinary new private super and mega power yachts are available for exclusive crewed charters in the Caribbean . Select the motor yacht charter in the Caribbean that suits all your demands: hire a yacht with water toys, chef, jacuzzi, helicopter, fitness center, and diving courses aboard. Enquire now about your private yacht charter Caribbean .

CATAMARAN CHARTER CARIBBEAN

Bareboat, skippered, and crewed catamaran charter the Caribbean for the day, 5 days, week, and 14 days catamaran rental Caribbean . Luxury and fully equipped catamarans up to 110 feet, spacious and comfortable, with flybridge, cook, hostess, jet ski, and air conditioning all-inclusive Caribbean yacht charters. From 4 to 10 cabins catamarans for your best Caribbean sailing holidays.

SAILBOAT CHARTER CARIBBEAN

Sailing the Caribbean aboard new boats in top conditions is a must: we provide the best bareboat, crewed and skippered sailboat rental Caribbean sailing vacations from 30 feet to 200 feet and 6 guests cabins. Caribbean sailing cruise aboard monohull Caribbean boats from the main bases of Leeward, Virgin and Windward Islands.

CREWED OR BAREBOAT?

The best selection of yachts for Caribbean boat charter includes extremely luxury cruises aboard power and sailing vessels with crew, for the most extraordinary, prestigious and regal experiences, getting the most exclusive services from your impeccable staff. Or opt for freedom and rent sailboat or catamaran in bareboat for your next sailing trips Caribbean.

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24/7 Assistance and free charter quotes

Share with your charter broke r's team all your necessities about your next Caribbean sailing vacations: period of the year and duration of the cruise, sailing or power yacht, number of guests and type of charter. Our experts are glad to assist you by phone, email, WhatsApp, and in person, reserving you the most appropriate yachting proposals. Thank you for the opportunity to serve you and have you aboard our exclusive Caribbean charters .

Your Boat Holiday 's services for your next Caribbean charters: The best new and refitted boats | Expert, professional and reliable crew members and local staff | Best deals and offers on charter market | Luxury yacht charter Caribbean with crew | Yachts with jacuzzi in the Caribbean | Private sailboat charters Caribbean | Crewed or bareboat catamaran sailing vacations the Caribbean | Top Caribbean yacht charter prices | Caribbean island hopping by boat | Best powerboat to cruise the Caribbean | Best sailboat for Caribbean |

Your yachting vacation in the Caribbean

Experience the boat rental Caribbean of a lifetime aboard our ultimate selection of luxury, comprehensive, professionally crewed catamarans, sailing or power charter yachts in the Caribbean. We will suite you with a charter yacht that best matches your budget and all the needs of your group. Our yacht charters permit you to enjoy everything from line-of-sight sailing in the Caribbean's clear turquoise waters. Or if you are looking for bareboat charter Caribbean, enjoy the freedom of a self-captained sailing vacation in the Caribbean calm waters. Board your luxury plot your course, catamaran, and island-hop through paradise at your own pace. Create your private own charter experience, aboard your high-performance sailboat or catamaran.

Caribbean Yacht Charters Itineraries

During your Caribbean yacht cruise itinerary, get to Grenadines and Saint Vincent , just the name evokes visions of exotic island and beach life. Close your eyes and imagine a stretch of white sand and crystal clear ocean, just you and your loved ones. Or sail in Antigua , enjoying sunsets and breathtaking views. Or if you are looking for the most exclusive Caribbean yacht charter destinations, cruise to St Barth and St Marteen. For some time the Caribbean has been the charter destination, a park that promises steady trade winds, warm seas, sparkling colors, and, of course, as many variations of rum punch as there are beachside bartenders to mix them. Recommended: Get the best Tortola charter to add more fun to your Vacation!

British Virgin Islands

Day 1st Norman Island Day 2nd Cooper Island Day 3rd Baths, Bitter End and Virgin Gorda Day 4th Beef Island Day 5th Great Harbour and Jost Van Dike Day 6th Peter Island Day 7th Tortola

The Grenadines

Day 1st  Martinica Day 2nd  St Lucia Day 3rd St Vincent Day 4th Bequia Day 5th Tobago Cays Day 6th Union island Day 7th St Vincent

Top Destinations in the Caribbean

Recommended: 7 top BVI charter yacht destinations to make your vacation better!

Enjoy your Yacht Rental in the Caribbean

You will enjoy excellent weather, breathtaking sights and a culture that encourages smiling, relaxation and romance. You, your family and loved ones will have a great time while also enjoying plenty of opportunities to sneak off alone and enjoy each others.

During a private yacht charter in the Caribbean , each Island is a breathtaking and lifetime surprise, always different and more exciting than the previous one. One island leads to another. Breathtaking, serene, and a vast expanse of lucid blue waters that let your eyes travel beyond and afar – such is the charisma of a Caribbean yacht charter voyage. 5,000 idyllic islands adorn the place in endless clusters.

Discover the hidden archipelago of Cuba or enjoy the 180 miles of the white sand beach of Abacos! The Caribbean hosts a number of tropical islands such as Bahamas, Barbados, Leeward Islands, Caicos, Windward, and Turks islands. The Bahamas itself hosts 700 islands, and Antigua comes with 365 beaches. Every island boasts a unique culture and portrays vibrancy in its landscapes. Moreover, travelers shall also get to savor the multifarious cuisines in these places, each more delicious than the other. Most of the islands host hidden beaches, dive shops, and sheltered anchorages. The Virgin Islands , Grenadines , Nevis, St. Martin , and Anguilla are popular spots to hit on a vacation. So? Wait no more and set sail ASAP!

Catamaran Charter in the Caribbean

One of the most popular modes of embarking on a yacht charter in Caribbean Islands is a catamaran. These catamarans, giving a luxurious feel, offer extensive platforms coupled with private en-suite cabins for the guests.

VIEW ALL THE CATAMARANS AVAILABLE IN THE CARIBBEAN

They also possess easy access through sugar scoops to the water and many luxurious indulgences such as shaded cockpits, forward trampolines, and in some cases, bridge decks in the upper fly as well. If you want solo cruising, then bareboat catamarans are the best! Why? Because they allow much more freedom to move around the deck and along the islands! Moreover, they consist of seating aft, thus, providing enough space to relax. With your sailing license, get set for your voyage soon!

When you have decided to opt for a yacht charter in Caribbean Islands, we promise that our rental services won’t squeeze your pocket! We provide a wide range of catamarans of every size and model to fit your requisites. Sail to your heart’s content and explore the exotic islands of Barbuda and Antigua, the US Virgin Islands and more.

Super Yachts in the Caribbean Islands

When it comes to crewed motor yachts, we know how deluxe your vacation needs to be! Sail away in the gorgeous turquoise blue Caribbean waters by chartering our crewed motor yachts and enjoy the five-star resort experience. You shall cruise comfortably, and your crew including the captain & the chef will assure your voyage to be an unforgettable one! The small motor yachts are perfect for a one-day cruise and can speed up to 40-50 knots. The larger ones are suitable for a 7 days Caribbean yacht charter itinerary.

VIEW ALL THE MOTOR YACHTS AVAILABLE IN THE CARIBBEAN

Here, we have an expert team of veteran skippers who ensure that the voyage is safe. Be it with your friends or family, hire our motorboats and visit the best of the Caribbean islands such as Trinidad, Tobago, British Virgin Islands , St. Barts , Jamaica, and many more.

Sailboat Charters in the Caribbean Islands

Powered by sails using the wind force, sailboats are referred to as dinghies, yachts as well depending on their sizes. They carry a cadence of heritage in their tenure. They range from light-weight dinghies which are 7’9” to superyachts that are about 200 feet long!

VIEW ALL THE SAILBOATS AVAILABLE IN THE CARIBBEAN

Imagine sailing on the transparent blue waters, the long wooden masts looking surreal in the setting sun’s scarlet hue; this is an ideal voyage for every wanderlust. You can witness such majestic scenario when you hire our bareboat sailboats as your Caribbean yacht charter. The wheel will be in your expert hands, and as you whisk away amidst the surging waves, your holiday only gets more enigmatic. However, if you are foreign to these waters, then we suggest you opt for our skippered vessels where experienced professionals will guide you safely.

Considering your vacation requirements, we provide you with sailboats that have been intricately engineered as per voyage tenures. Our vessels are designed by acclaimed architects; so, you can travel with peace of mind knowing that you will be safe on the water. We house a troupe of experienced skippers who have extensive knowledge about the locales you choose to visit!

The Bahamas

The Bahamas should be a must-visit place for any adventurous soul who is also keen on history. This is an archipelagic state with many islands that cover over 470,000 square kilometers of ocean. It joins the Caribbean with the United States’ coastal reached and especially Florida . This place sure has an intriguing history that tells how the British ousted the cunning pirates from its shores. The walls of Fort Charlotte and the neoclassical patterns of Bahamian Parliament are wonders to look at.

Turks and Caicos

The Cockburn Town’s salt-washed jetties, idyllic Providenciales, 300 mini islets placed amidst the Lucayan Archipelago and what not! What else could you find in this intrepid island? This U-shaped land portrays pirate carvings that date back to the 19th century. Its sprawling coral gardens are the perfect scuba diving spots. Many of the islets are mere sandbanks or even rough rock pillars which rise above the Caribbean Sea waters.

Antigua and Barbuda

Any yacht charter in Caribbean Islands will take you to these places for sure. Located in the middle of Leeward Islands, this duo quips for being one of the most favorite tourist spots in the Caribbean area. Pearl white beaches of the Shirley Heights Lookout located in Antigua along with its soothing palm forests indeed make this colonial town a serene place to hop in. As for enjoying solitude in real bliss, Barbuda proves to be the right spot for solo travelers.

Dominican Republic

Stretched across two-thirds of Hispaniola Island, the Dominican Republic is a convenient travel spot especially for North Americans. Santo Domingo, its capital, boasts a lot of attractions, and tourists usually flock in as they can indulge in many activities here! Arid deserts, lush rainforest and divine alpine ranges make this terrain an exotic and diverse spot to visit. The historic colonial architecture of this village and the remarkable mountain retreats are a vision to behold! If you stop in the capital for a day to two, then do relish the colonial-era relics of the place.

Adventure! This is the one word that defines Haiti. Unlike the other Caribbean islands, this place is all about exploring and experiencing nature’s best. The turquoise waters of Labadee, Jacmel’s palm-fringed beaches, Citadelle Laferriere’s juggernaut walls and many more places make Haiti a wild and adventurous zone for everyone. Thus, it becomes a must-go spot on your Caribbean yacht charter itinerary! Amidst the scarlet sunsets, pinkish dawns, and tranquil dusks, nature shall truly become yours when you set sail on the waters of the Caribbean.

Caribbean Yacht Charter Experts

The Your Boat Holiday 's Caribbean Yacht Charter Managers check and update our selection of sailing and power yachts regularly, establishing long-lasting relationships with crew staff and local operators. That's the reason why our team is professionally placed to offer you tailor-made and transparent support for your boat rental Caribbean . We developed more than twenty years of charter experiences in the Caribbean Sea, which allow us to achieve always our customer 100% satisfaction and to maintain fruitful cooperations with our highly qualified partners.

Recommended: How much does it cost to rent a yacht in the Caribbean?

Our Featured Yacht Charters Destinations: BVI yacht charter - Grenadines yacht charter - Antigua yacht charter - Cuba yacht charter - St Lucia yacht charter - Mauritius catamaran charter - Aeolian Islands yacht charter - Capri yacht charter - Amalfi Coast by boat - Mykonos yacht charter - Santorini yacht charter - Ibiza yacht charter - Cannes yacht charter - Olbia yacht charter - Greece catamaran charter

Sailing Qualifications

To skipper a bareboat charter or flotilla yacht, you need to hold a practical sailing certificate equivalent to RYA Day Skipper Practical qualification or RYA International Certificate of Competence (ICC) . For charters in Greece, you must now have the ICC certificate . You must also be assisted by at least one competent crew member over the age of 18.

The port authorities in Greece are now insisting on one of the following practical certificates: RYA ICC (International Certificate of Competence), RYA Coastal, RYA Yachtmaster, ASA IPC (International Proficiency Certificate) or the IYT (International Yacht Training) Passport. If you hold an RYA Day Skipper or ASA104 it will no longer be accepted and you need to obtain either an ICC or IPC from the corresponding issuing body (RYA or ASA). If your RYA Coastal/Yachtmaster or ASA105/106 certificate is more than 12 years old and does not have a photo ID, then we would also strongly advise applying for an ICC or IPC. If you are a member of the RYA or ASA, you may qualify for a discount or free certificate, otherwise, you will have to pay. The approximate cost is £50. Please use this link - RYA application for the ICC or ASA application for the IPC.

For charters in Croatia, Malta and the Canaries , at least one member of the crew or the skipper will also need a VHF licence .

RYA qualifications can be obtained by RYA sailing schools in the UK or alternatively choose from one of our overseas centres in Gibraltar, Greece or Turkey .

For  Seychelles,  the local authorities require an ICC for the skipper of a bareboat or flotilla yacht charter.

For Caribbean and Tropical charters, formal qualifications are not compulsory, however, you should be Day Skipper standard and be assisted by at least one competent crew . A brief sailing resume should be provided to outline your experience.

For Thailand A Day Skipper qualification is required as a minimum and you must have at least 3 weeks of skippering experience prior to your charter. A VHF qualification is compulsory.

If you don't hold the relevant qualifications then why not add a skipper ?

Sailing Levels

Winds force 2-3 (4-11 Knots)combined with generally shorter distances. Good for beginner or intermediate sailors. Line-of-sight navigation but basic knowledge of charts and ability to plot your position required.

Winds force 3-5 (7-21 Knots) with approximately 15-20nm per day. Intermediate experience required. Predominately line of sight navigation but an understanding of how to sail in open water.

Winds force 4-6 (11-27 Knots) with mileage of approximately 20nm+ per day. Ideal for experienced skippers looking to venture out to new destinations. Day skipper standard but with experienced crew would be recommended.

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Caribbean sailing holidays.

Anchor off your own white sandy beach. Dive into warm turquoise seas to snorkel among the rainbow colours of a coral reef. Relax with a rum punch sundowner on the deck of your yacht while you watch another glorious sunset....

Click on the cruising areas below for more details on sailing in the Caribbean. 

With 365 palm-fringed beaches and numerous anchorages, Antigua offers excellent sailing round the island. As part of the Leeward Islands, Antigua boasts a spectacular choice of picturesque coves and bays, with fine sand, blue seas and some of the best watersports in the Caribbean.

Cruise the "out islands" of the Abacos, just 1 hour flying time from Miami, an archipelago of pale sandy islands, tranquil bays, sheltered harbours and sleepy historic villages. The beaches are spectacular, mile after mile of white sand and plenty of reefs for fantastic snorkelling and scuba diving.

Belize is located on the Caribbean coast of Central America, South of Mexico. Home to the second longest barrier reef in the world, Belize offers superb calm water sailing, diving and snorkelling, Mayan ruins and more - truly an unspoilt holiday getaway.

British Virgin Islands

Come and see for yourself why the BVI is the most popular cruising area in the Caribbean. Perfect sailing conditions and sheltered passages round the islands make this area a delight for all levels of sailors wanting to relax in a Caribbean paradise. Great choice for a first Caribbean charter.

Cuba is a magical new destination for experienced sailors with some of the world’s finest beaches, a rich cultural heritage and a vibrant approach to life. Dive and snorkel on some of the most exquisite coral reefs in the Caribbean and when the sun goes down, party to the salsa rhythms.

Explore these Robinson Crusoe islands with soft white sand, turquoise seas and spectacular coral reefs. The Grenadines are undeveloped and unspoilt. Nightlife is conspicuous by its absence, peace and solitude are unsurpassed, and the dress code - like the lifestyle - ranges from informal to barefoot casual.

Cruise around this butterfly-shaped island with a French Creole flavour or sail to neighbouring Antigua. On Guadeloupe the beaches are secluded and the smell of fresh croissants and pastries mixes everywhere with the spicy aromas of West Indian cooking in restaurants and charming bistros.

Martinique is more relaxed than the Caribbean islands to the north and more sophisticated than the islands to the south. The French influence ensures excellent restaurants. Spend a whole week exploring Martinique or head north to undiscovered Dominica or south to St Lucia.

This surprisingly little island embodies a dual personality - half French, half Dutch. St. Martin/St. Maarten and the surrounding islands of Anguilla and St Barths offer some of the most spectacular sailing in the Caribbean. Experience beautiful anchorages, stunning sunsets and outstanding restaurants.

Ask us for a Quick Quote We'll get back to you with a no obligation tailored quote within 24 hours ( Mon-Fri: 0900-1730 )

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Sailing Holidays in Caribbean

A nautical dream come true!

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Up to 35% discounts and extra 5% on all bookings made until November 30th, 2023

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What makes Caribbean so attractive for sailing?

The Caribbean is a group of islands which is located on the Caribbean Sea to the East of North America, simply known to as “paradise on earth!”

Whether you’re planning a family vacation with the whole crew, a romantic getaway for two , searching for calm, preserved waters and short island hops or exhilarating blue water passages, the Caribbean is one of the most exciting sailing vacations you could ever experience.

Currency: East Caribbean Dollar, United States Dollar, Euro

Sailing season and climate

The climate in the Caribbean is tropical which means that the weather is hot and sunny all year long. Although most of the islands start their rainy season from May to October, the official hurricane season in the Caribbean begins from 1st of June until the 30th of November.

Caribbean yacht charter options

Tailored yacht vacation

Tell us everything you want to experience and explore and we will get started on working towards making your dream sailing trip come true

All-Inclusive or self-catered, it’s your choice. These sailing trips are tailored to bring family close.

Romantic sailing holidays

Is there a better way to explore some of the world’s most romantic holiday destinations but island hopping with your private boat charter?

Bareboat Charter

Boat rental without any crew member. With a valid sailing license, you sail the boat by yourself.

Skippered Yacht Charter

Yacht charter holidays with a professional skipper and other crew members on request.

Luxury Sailing Yacht Charter

Embark on your next sailing trip with class! We strategically plan your luxury sailing holiday to suit all your wishes.

In case you are a solo traveler, couple or a smaller group, and want to have a wonderful sailing experience, but are not able to afford a whole boat charter, cabin charter is a great and accessible option for you!

Pick a route for your perfect sailing holiday

7-Days Sailing around BVI

This 7-day sailing itinerary promises a perfect blend of adventure and relaxation, offering a firsthand exploration of the BVI’s pristine beaches, vibrant coral reefs, and charming coastal villages.

7-Days Itinerary for Family Sailing Holidays in Bahamas

Embark on an unforgettable family sailing adventure in the Bahamas, where crystal-clear waters, white sandy beaches, and warm hospitality set the stage for a perfect nautical getaway.

Didn‘t find what you were looking for?

No problem! Reach out and let’s create your custom route together.

Top Caribbean Sailing Destinations

Cuba is located in the Northern Caribbean where the Caribbean Sea, the Gulf of Mexico and the Atlantic Ocean meet.

BVI (United Kingdom)

You would definitely fancy a BVI sailing trip as it is known to be one of the top sailing destinations in the world.

Saint Martin

Saint Martin is an island in the Northeast Caribbean Sea, approximately 300 km East of Puerto Rico.

Antigua and Barbuda

Antigua and Barbuda is a country in the West Indies in the Americas, lying between the Caribbean Sea and the Atlantic Ocean

Saint Lucia

This part of the world offers some of the most vibrant and colourful snorkelling in the Caribbean and where you can relish a warm welcoming and sensational French Creole culture.

In Martinique, you could take joy in swimming and snorkelling among coral reefs or stay at the lovely fishing villages, hot springs, lush rainforests and rugged peaks.

Saint Vincent and the Grenadines

This is a magical destination where the only limit is your time and how much you can pack into your itinerary.

Sint Maarten

The islands generally experience low humidity and recurrent droughts. The average temperature is 27 °C and the coolest period is between December and February.

The Bahamas

A tropical paradise that has been a top family vacation destination for decades

Cuba is located in the Northern Caribbean where the Caribbean Sea, the Gulf of Mexico and the Atlantic Ocean meet. Major cities include Havana which is the country’s capital capital and the largest city while other major cities include Santiago de Cuba and Camagüey. It is popular with sailors for its favourably warm climate, steady winds, natural beauty, and unbiased welcoming people.

– Official language: Spanish.

– Currency: Peso (CUP).

– Local climate: tropical, moderated by Northeasterly trade winds that blow all year long.

– Cuban culture: influenced by its melting pot of cultures, primarily those of Spain and Africa. In addition, most charter fleets are situated in Cienfuegos.

– Marina facilities: water, electricity, restaurant, bar, mini-market and washing facilities.

Beaches of BVI

The British Virgin Islands consist of the main islands of Tortola, Virgin Gorda, Anegada, and Jost Van Dyke, along with over 50 other smaller islands and cays. You would definitely fancy a BVI sailing trip as it is known to be one of the top sailing destinations in the world. With near-constant gentle trade winds, easy line-of-sight navigation and short leg voyages between the islands, it is a favourite for novice and seasoned sailors alike.  

– Capital: Road Town

– Currency: the US Dollar (USD)

– Official language: is English  

The British Virgin Islands have a tropical rainforest climate which is moderated by trade winds. The sailing route can begin in Saint Thomas, which then takes you to St. John, Tortola, the Bight, the Indians, Cooper Islands, Salt Island, Trellis Bay, The Baths, Gorda Sound, The Dogs, Great Harbor, Green Turtle Cay and finally Cane Garden Bay. On your way, you should definitely stop to explore the wildlife, the caves and go snorkelling.

Saint Martin is an island in the Northeast Caribbean Sea, approximately 300 km East of Puerto Rico. The 87-square-kilometre island is divided roughly 60/40 between the French Republic and the Kingdom of the Netherlands. Sailing from St. Martin allows you to explore some of the marvellous islands in the Eastern Caribbean, including mainland St. Martin, Anguilla and St. Barts. As for the divers and the snorkelers, they can enjoy some of the most spectacular unspoiled reefs in the world.

Currency: Euro

Capital: Marigot

Antigua and Barbuda is a country in the West Indies in the Americas, lying between the Caribbean Sea and the Atlantic Ocean. It consists of two major islands, Antigua and Barbuda, and a number of smaller islands. There is said to be 365 distinct beaches on Antigua, perfect to visit one for every day of the year. This region is one of the world’s most desirable sailing destinations along with its complex coastline, an abundance of safe harbours and a nearly unbroken protective coral reef.

The capital: St. John’s on Antigua  

The official language: English

Currency: East Caribbean Dollar (XCD)

The islands generally experience low humidity and recurrent droughts. The average temperature is 27 °C and the coolest period is between December and February. The sailing route can consist of a one week sailing trip around the island of Antigua which means starting in the capital of St. Johns and sailing away to Jolly Harbour, Carlisle Bay, English Harbour, Green Island and Dickenson Bay.

Saint Lucia is a sovereign island country in the West Indies in the Eastern Caribbean Sea on the boundary with the Atlantic Ocean. This part of the world offers some of the most vibrant and colourful snorkelling in the Caribbean and where you can relish a warm welcoming and sensational French Creole culture.

Currency: East Caribbean dollar (XCD)  

Capital: Castries  

The volcanic island of Saint Lucia is more mountainous than most Caribbean islands, with the highest point being Mount Gimie. The local climate is tropical, moderated by northeast trade winds, with a dry season from 1st of December till the 31st of May, and a wet season from 1st of June till the 30th of November. While sailing in St. Lucia, you will see why the island is famous and filled with sailors, as it is a fantastic mid-point to explore the Grenadines and the astonishing Caribbean islands.

Explore St. Lucia’s Rodney Bay in the North, where you can discover the Pigeon Island National Park, or visit Vieux Fort Wetlands in the South. If you enjoy hiking, the Gros Piton Nature Trail between the Piton’s volcanic peaks is a must see as it has one of the most impressive views in the Caribbean.

Martinique is one of the eighteen regions of France (being an overseas region) and an integral part of the French Republic. In Martinique, you could take joy in swimming and snorkelling among coral reefs or stay at the lovely fishing villages, hot springs, lush rainforests and rugged peaks.

Official language: French

Currency: Euro  

Capital: Fort-de-France

The capital celebrates every aspect of the French culture with style and panache from their excellent cuisine to the chic sophistication of fine resorts and hotels. While sailing in Martinique, just like sailing in Antigua, your route consists of sailing around the island and most of the charter fleets are situated in Le Marin.

Saint Vincent and the Grenadines is a country in the Lesser Antilles Island Arc, in the Southern portion of the Windward Islands. In fact, out of their 32 enchanting islands, only 9 of which are inhabited, including Mustique, Bequia and Union. St. Vincent, while the largest island is your gateway to the Grenadines with us! This is a magical destination where the only limit is your time and how much you can pack into your itinerary. You may even wish to consider a 14-day stay to explore this wonderful cruising ground.

The capital: Kingstown

On your sailing trip, you could consider visiting St. Vincent, Mustique, Canouan, Mayreau, Tobago Cays, Union Island, Clifton Harbour and Chatham Bay.

Sint Maarten is the southern Dutch part of Saint Martin island and is one of four constituent countries that form the Kingdom of the Netherlands. It is commonly believed that Christopher Columbus named the island in honor of Saint Martin of Tours when he encountered it on his second voyage of discovery.

Sint Maarten is 34 km2. The terrain is generally hilly, with the highest peak being Mount Flagstaff at 383m. The area to the west around the airport is flatter and contains the Dutch section of the Simpson Bay Lagoon. The Great Salt Pond lies to the north of Philipsburg. Several small islands lie off the coast (Cow and Calf, Hen and Chicks, Molly Bay, Pelikan Key, Guana Key of Pelican). It is home to many distinctive plants: hibiscus, yellow sage, mahogany, and cacti.

In March there is an annual regatta being held. It lasts three days and is culminating in the first weekend in March. There is also the annual St. Maarten Carnival which starts in April and ends in May.

The island is famous for its Maho Beach which is right next to a runway at Princess Juliana International Airport. Landing aircraft pass within 35 meters from the beach.

Nightlife full of festivities, beautiful beaches, traditional and delicious cuisine, and grandiose casinos make Sint Maarten a great place to spend your sailing holidays.

Currency: Netherlands Antillean Guilder  

Capital: Philipsburg

Bahamas week sailing route

Have something else in mind.

Bahamian coast is very long, compared to the total area of the country. This is due to a large number of islands, islets, atolls and cays. In large numbers, the islands are rounded, with a large number of coves and a very sandy bottom, ideal for sea fun – swimming, diving and underwater safari. Sailing in the Bahamas is popular because of the aforementioned relief features. 

One of the features of the Bahamian coast is coral reefs from which the atolls develop, shallow islands rounded up in the lagoons. There is growing awareness about the conservation of beautiful coral reefs, which are more and more damaged due to climate changes and pollution of the oceans. As the Bahamas are surrounded by the ocean, there are few places where there are no coral reefs on all sides of the island. The shores of some islands in the Bahamas are a bit steep, with much deeper ocean depths.

Currency: Bahamian dollar (BSD)

Language: English

Coastline: 3542 km 

Number of islands : over 700, including cays (small sandy islands)

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Picking a boat type.

Picking out the type of boat to go with will generally come down to your budget, the group size, and preferred method of sailing. Moreover, different sailboats available can be chartered independently or with a fully-staffed crew.

Starting from 160 EUR per day

Starting from 500 eur per day, have a question we have the answer, enquiry about caribbean, requirements for bareboat charter.

In order to be able to charter a bareboat in the Caribbean, the skipper is required to fill out a questionnaire and the sailing experience they had. No official sailing license is necessary to have on hand, however, before making any reservations, we advise you to check all the requirements with your agent. Otherwise, we can provide you with a local professional skipper and other crew members (such as hostess and a chef) to attend to you and make your sailing experience a holiday to remember!

Feel free to ask us anything. All hands on deck. Let's sail

Thank you for sending us an inquiry, thank you so much for your enquiry.

Bareboat, Skippered and fully Crewed Yacht charters.

Relax, sail and explore onboard your yacht on the Caribbean azure.

Top notch bareboats, sensational catamarans, magisterial mega yachts and cabin charters for your amazing sailing holidays.

Why book your Caribbean yacht charter with Oceanedia Sailing Holidays?

We offer expert advisory, with years of local knowledge, in partnership with the best yacht charter providers in the Caribbean.

The Caribbean

Experience the cultural diversity, cuisine, vibrance and jaw dropping seascapes of the Caribbean by yacht charter.

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Worldwide Yacht Charter

Yacht Charters in St Vincent and the Grenadines

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Yacht Charters in St Maarten

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Yacht Charters in the Bahamas

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Caribbean Catamarans

Croatia yacht charter holidays, caribbean sailing holidays by oceanedia.

An Enviable Lifestyle

Whether it’s skimming jewel coloured waters between Antigua and the Grenadines or mooring in a picturesque anchorage off the coast of the British Virgin Islands. Caribbean Sailing Holidays by Oceanedia, offers a fleet of private, luxury crewed yachts for the discerning and stylish vacationer. Discover the colour and culture of the Caribbean, the art deco havens of Florida, the magic of Mexico’s east coast beaches, and the aquatic enclaves of South America.

Meet the Fleet

Caribbean Sailing Holidays works in partnership with long established yacht charter providers and holds access to some of the world’s most sophisticated luxury yachts directly. Select 10m to 100m, classic, vintage, motor and sail. Between November and June, you can circumnavigate Bermuda and the Caribbean or discover Mexico and South America, with a hand-selected team of service staff and highly experienced qualified professional captain and crew.

The Caribbean Sailing Holidays’ range of Motor Vessels and Sailing Yachts, our luxury yacht range boast sun-drenched entertaining areas and exquisite open-plan spaces, akin to a premium hotel interior.

Unwind in the ambient lounge with cocktail and canape in hand or take in the balmy evening breeze under a scattering of stars. At night, when gentle waves lull you into the deepest of sleeps, retire to the most beautiful boudoir, complete with ensuite bathroom.

Desirable Destinations  

From diving into azure waters in the Florida Keys, The Bahamas, Antigua, Martinique, Guadalopue, St Lucia, Grenada, St Vincent and the Grenadines, The British Virgin Islands, St Barth’s, St Kitts and Saba to wandering ashore to sample the divine cuisine of Cozumel, Anguilla and St Martin, Caribbean Sailing Holidays with works with you, to map the route to paradise. We know every sugar white shoreline, picturesque city and secret cove around the Caribbean and adjacent shores and waters. Whether you dream of cosmopolitan chic or to glimpse ancient relics, we will help you discover it.

Work on a caramel tan in the tantalising Turks and Caicos before exploring the Mayan Ruins near La Amada marina in Mexico. For the truly adventurous, charter your way to the bays of Colombia, to the historic town of Santa Marta.  

And if blissful 181 islands of Bermuda beckons, you can experience the glamour of Caroline Bay and the palm-fringed City of Hamilton – both favourite destinations during America’s Cup, the world’s eminent yacht sailing race.

Enquire Now

Ready to go on a voyage of discovery? Seeking a lavish vacation that will linger long in the mind? Contact Caribbean Sailing Holidays by Oceanedia today to design an unforgettable yacht charter – entirely bespoke, secure and private.

You only live once. It’s time to tick the bucket list. Those warm tropical waters and powder soft sands are inviting you in. Step aboard. Take the plunge. Live the ultimate dream.

You make the memories. We make the arrangements.

Amazing Caribbean Yacht Charter Holidays

Whether sailing with family, friends or even your colleagues, a holiday yacht charter will surely...

Whether sailing with family, friends or even your colleagues, a holiday yacht charter will surely be one of the most memorable vacations you have ever had. Here are 5 reasons you should book your amazing Caribbean yacht charter holiday now. On an Amazing Caribbean Yacht Rentals .

1. Early planning ensures a more relaxed holiday.

It’s never too early to start planning your next yacht charter vacation! By booking early, you can ensure that you get the best boat for the destination of your dreams. The holidays are already stressful enough, so why not take care of your vacation plans now so that you won’t stress about them later? The sooner you book, the more likely we will be able to accommodate your preferences and holiday schedule.

2. The best boats may sell out for specific dates.

It’s always best to book your charter early, especially if you have your heart set on a specific boat or destination like the Virgin Islands or the Bahamas over Christmas or New Year’s Eve . If you’re planning to charter during peak season, booking early is essential, as boats tend to fill up quickly.

Power catamaran FRENCHWEST is a top-rated boat that is perfect for families.

The yacht was beautiful, very new and very well maintained. It was well beyond our expectations. The rooms were spacious and comfortable. The size of the boat was great for 6 people plus crew, we had plenty of room all over the boat to hang out. FRENCHWEST charter guests Summer 2022

3. Enjoy a personalized gourmet Thanksgiving.

Thanksgiving is a time to indulge, and there’s no better way to do that than by chartering a yacht with a private chef. The chef will prepare a menu that includes all your holiday favorites. And what’s more, you can enjoy them while relaxing on the deck of your beautiful yacht, surrounded by family and friends.

And don’t worry about missing any vital football games, either. Your yacht is equipped with the latest TVs and WiFi connectivity. Moreover, you don’t have to do any dishes after your delicious meal.

TAIL LIGHTS is a 116-foot Azimut motor yacht that accommodates 12 guests in 5 spacious cabins. Loads of water toys and other amenities make this a fantastic choice for larger groups.

4. Celebrate Christmas and New Year’s Eve in style.

If you’re looking to celebrate Christmas and New Year’s Eve in bespoke style, then booking a holiday Caribbean yacht charter is a perfect way. Not only will you enjoy the beautiful weather and scenery, but you’ll also be able to relax and escape the hustle and bustle of the holiday season.

Picture yourself having Christmas dinner in the tropics rather than in the cold. You’ll feast on gourmet meals, travel from one lovely island to the next, and even have a unique holiday surrounded by those you love. Best of all, you don’t have to shop, cook, or clean up!

And this year, instead of the usual eggnog, why not swap a traditional tropical cocktail with a Christmas twist? Why not try a Cranberry Margarita? Here’s the recipe:

Yacht Holiday Cranberry Margarita

• 2 oz cranberry juice
• 1 oz fresh lime juice
• 1.5 oz blanco tequila
• 0.5 oz Cointreau (optional)
• 0.25 oz simple syrup or agave syrup
• Fresh cranberries and lime for garnish

Combine all ingredients in an ice-filled shaker and then pour into a salt-rimmed glass over ice cubes. Garnish with cranberries and lime slices. Enjoy!

EROS , a classic 115-foot sailing yacht, will delight everyone in your group. Imagine a champagne toast while watching New Year’s Eve fireworks on the deck of this remarkable vessel!

5, Make your next Valentine’s Day the most romantic ever.

How about celebrating Valentine’s Day on your private yacht? Surprise someone special with champagne, roses, and an intimate dinner together in the most romantic setting. Your crew will pamper you and make sure you have everything you need, including privacy. It’s nice to be pampered but being pampered in paradise makes it an experience to remember!

Reserve Your Amazing Caribbean Yacht Charter Holiday Now

The Caribbean is a beautiful place to spend your holidays, with plenty of fun-filled activities. If you’re planning on going during Thanksgiving, Christmas, New Year’s Eve, or Valentine’s Day, the best thing you can do is book early.

Call to find your Amazing Caribbean Yacht Rentals today. 321-777-1707 .

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Contact us to start a conversation about your dream vacation, and let us show you how we can help bring your vision to life through our exceptional yacht charter services.