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The state of Florida in the United States is home to some of the most popular boating destinations and cities such as Miami and Fort Lauderdale. While these areas offer many boats, Miami and the Florida Keys have some beautiful sailing conditions, which makes sailboat rental in Florida particularly popular.

Pricing and Info on renting a sailboat in Florida.

To rent a sailboat in Florida, prices cost around £500 for the day, while renting a sailboat in Florida for a week will average at around £4000. These prices vary however, due to the type of boat and the time of year you want to go.

Sailboat availability in Florida

Because Florida is sunny year-round, it does not follow the conventional sailing season. The peak season will typically run from December deep into February, but sailing still goes strong into May. If you’re looking to avoid the influx of tourists, then sailing in the months of April and May is perfect for you. Outside of this period, you’ll still have plenty of sunshine, but you’ll also have heavier periods of rain and humidity. Even in the low season sailing is very popular in Florida, and so you should always book far in advance.

Do I need a license to rent a sailboat in Florida?

To rent a sailboat in Florida, you do not need a license, however, if you were born on or after January 1st of 1988 you will need to obtain a Boating Safety Education Identification Card, which will require you to complete an approved Boating Safety Course. Also, if you are 18 years old or younger, you cannot rent any sort of watercraft.

If you do not have a licence or sailing experience, you can rent any of our sailboats with a skipper from our catalogue. When you rent a skippered sailboat, you can relax and enjoy your trip. The skippers help you to get to know the places you visit by boat in depth.

Overview of Florida

Undoubtedly one of the best areas to sail in the USA is Florida. With the sunshine year-round, you’ll always have perfect conditions to explore this beautiful state by boat. Due to its geographical position, it’s a sailor's paradise with an endless coastline that is available. If you’re living in the US, it’s the perfect place close to home; if you live abroad, it is more than recommended to make the trip.

In Florida, you’ll have several options for where to rent a boat. One of the most popular destinations to sail in Florida is the Florida Keys. Rent a boat in Key West, here you will have access to some of the best island hopping and you will be able to create a unique journey. Seeing the different islands and several coves is a highlight of any vacation. If you plan on sailing in the Florida Keys, chartering a yacht for at least is the right way to go.

Besides the Florida Keys, you’ll also be able to rent a boat in Fort Lauderdale. Fort Lauderdale is the perfect departure point for seeing the coast of Florida. Because of its location, you’ll have access to hot spots like Miami or sail down to the Florida Keys. Either way, you’ll surely have the perfect sailing holiday in Florida.

Due to the popularity of sailing in Florida, it is no wonder sailboat rental is so popular, as the sailing conditions are some of the bests you will find in the US, particularly in the Bay of Florida, with Miami and the Florida Keys, in particular, being a popular area to rent a sailboat.

Sailing areas around Florida:

• Florida Keys
• Fort Lauderdale

Our other types of boats

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Sailboats Unlimited

Bareboat and Crewed Sailing Charters

Bareboat and Crewed Sailing Charters in Naples, Florida since 1985!

Crewed Sailing Charters

Choose from a 2 hour “taste of sailing”, a half-day “jaunt along the beach” sailing the wind, a full day “adventure to Marco Island” sightseeing or romantic sunset or moonlight cruise.

Bareboat Charters

Let us help you plan a complete Florida sailing vacation from a simple overnight to a couple of weeks

Types of Charters

Choose your desired charter.

When choosing a sailing charter, you want to choose with confidence. Established in Naples in 1985, providing romantic getaways, sunset/sunrise trips, once in a lifetime sailing experiences for families on vacation, and corporate team building adventures.

About sailboats unlimited, naples most trusted sailboat chartering company since 1985.

The best experience you will have while visiting beautiful Naples, Florida

Located in sunny Naples, Fl, we have specialized in crewed sailing charters, bareboat sailing charters, yacht deliveries, and yacht maintenance since 1985.

When visiting Naples, FL or any of the surrounding areas, you have the opportunity to take our sailboats out onto the beautiful gulf. Let us charter you and your guest, or reserve the entire yacht for your guest. Sunset and moonlight cruises, half day and full day cruises. We have something for every scenario.

Our bareboat yacht charters are on boats ranging from 34′ to 42′. Half day to weekly bareboat charters are available. Preliminary checkout available by phone or fax. Prices vary depending on vessel. 34′ ocean racers and up to 42′ luxury cruising yachts. Large parties can be accommodated, with up to 16 on the Danmark, a 40′ Sloop U.S. Coast Guard inspected vessel.

Enjoy the unique Florida experience sightseeing and watching the dolphins at play. Kick back and be pampered or you take the helm. Free sailing instruction during the charter.

Beachside Sailing

Sailing Lessons and Rentals

Sailboat Rentals

Sailboat Rentals in Port Canaveral and Merritt Island, Florida, near Cape Canaveral, Cocoa Beach and Orlando, FL.

Our sailboat rentals are affordable and conveniently located near many Orlando and Central Florida attractions, just a short drive from Walt Disney World.  We have boats available in Port Canaveral and Merritt Island, located near Cape Canaveral, Cocoa Beach and Titusville, Florida. Our locations allow quick access to the Indian River, Banana River, and Atlantic Ocean.  Our sailboats can accommodate multiple persons, so please click here or call us at (321) 624-5537 for more information about our sailboat rentals, sailing school and other Sailing events.

Florida Keys Sailing

Private liveaboard classes, come sail with us.

Proud Member of the ASA

At Florida Keys Sailing our specialty is: Private Live Aboard Sailing Classes and Sailing Vacations with just you and your spouse or friends. “Learn to Sail” or take an Advanced Class to develop your skills. Qualified sailors can Charter our boats. A Captain will happily take you and your family on a Day Sailing Trip if you need one. Many sailing classes offered elsewhere crowd you on a boat with a group of total strangers.

At Florida Keys Sailing ALL of our Sailing Classes, Day Sailing Trips, and Private Charters are exactly that…PRIVATE.

No one else except YOUR Party is ever on-board. This means you will learn more by having more time DOING, not WATCHING someone else sail. Dollar for dollar you will find more VALUE in taking your Sailing Courses at Florida Keys Sailing.

Or download the form here

Fun on the Waves

Our Classes

To learn more about the liveaboard classes we offer, visit our classes page

2 DAY BASIC FUNDAMENTALS OF SAILING

Designed for beginners who want the best introduction to the exciting sport of sailing. Students will receive a good understanding of all the “Basic Fundamentals of Sailing”. They will leave as very competent Crew Members.

3 DAY BASIC KEELBOAT “LEARN TO SAIL CLASS”

Beginner students will learn to responsibly be the Skipper of a Day Sailing Keelboat in familiar waters in moderate wind and sea conditions. Classes available are year round on demand based on your travel plans.

5 DAY BASIC COASTAL CRUISING OR 101 & 103

Students will learn to responsibly skipper and crew an auxiliary powered cruising sailboat during daylight hours within sight of land in moderate wind conditions. This Private Live Aboard Class is taught aboard our Catalina 30' or Irwin 34 Offered all year on demand based on your travel plans.

5 DAY BAREBOAT CRUISING OR 103 & 104

Charter a cruising sailboat during daylight hours in most wind and sea conditions. This Private Live Aboard Class is taught aboard our Irwin 34. Offered all year on demand based on your travel plans. 5 Days and 4 Nights…Privately Living aboard at our Dock

3/1 DAY ADVANCED COASTAL CRUISING OR 106

Cruise a sailboat during nighttime hours in most wind and sea conditions. A Private Live Aboard Class is held aboard our Catalina 30 or Irwin 34. Offered all year on demand based on your travel plans. 3 Days and 3 Nights…Privately Living Aboard

7 DAY BAREBOAT CRUISING OR 101, 103 &104

Charter a cruising sailboat during daylight hours in most wind and sea conditions. This Private Live Aboard Class is taught aboard our Irwin 34 This is the Class the Bareboat Charter Companies want you to have. Offered all year long on demand based on your travel plans. 7 Days and 6 Nights…Privately Living Aboard at our Dock

3 DAY FAST TACK TO CRUISING ASA 101 & 103

It’s the fastest and least expensive way to get the first 2 – ASA Certifications. Both combined into a 3 Day / 2 Night Live aboard Class. Prior sailing experience before enrolling is advised. Only $2,039 per student! And better yet…a second student enrolls for FREE!

5 - DAY FAST TACK TO BAREBOAT CRUISING ASA 101, 103 & 104

It’s the fastest and least expensive way to get these 3 - ASA Certifications. All 3 are combined into a 5 Day / 4 Night – Live aboard Class. Prior sailing experience before enrolling is advised. Only $3,599 per student! And better yet…a second student enrolls for FREE!

Testimonials

Daysailing & charters, we offer both daysailing and charters, click below to learn more.

Private & Shared Sailing Charters

Sunset sail key west.

Have the sea to yourself with Sunset Sail Key West—chartered sailing trips led by us, tailored to you.

Get inspired with our most popular trips!

Private sunset sail.

Chillout Lilypad Sail

Key West Daysail

Sunset Sail on When & If

Privates Charters

Discover your perfect private charter.

Set out on a snorkeling, stargazing, or sunset sail, or build your own custom trip. Romance, relax or unwind from the privacy of your own chartered sailboat.

Shared Trips

Come together on a shared charter.

Rise above the crush of the crowds and set sail on a unique shared sunset charter, with a few friends you haven’t met yet. A personable local crew and captain will treat you to a stunning sunset view from the deck of an unforgettable vessel– General Patton’s elegant, private schooner When and If.

Three Classic Boats

View our fleet.

We sail a fleet of three vintage sailboats, each with their own unique charm and appeal. A custom sloop, a classic ketch, and a historic schooner are waiting to make memories with you on the crystal clear waters of Key West. Each boat is suited to different types of outings, so take a moment to get acquainted with our vessels.

Real. Fun. Sailing.

When And If is back at beautiful Stock Island Marina!

Check Out Our Ship's Store!

Wreckers' Race Season Is Back!

Hello, Sailor! Don’t miss out on the latest Sunset Sail news & offers.

Friends of SSKW

Legal & safety.

• Sailboat rental
• Boat rental

Beneteau Oceanis 51.1  (2019)

From $737 per day.

Beneteau Oceanis 51.1 Avocado  (2019)

Sailboat Bavaria 46 cruiser 13.99m  (2007)

From $352 per day.

Bavaria 36  (2002)

From $447 per day.

Sun Odyssey 440  (2023)

From $809 per day.

New Beautiful Dufour 390 Grand Large  (2022)

From $553 per day.

Oceanis 41.1 - IBIZA  (2019)

From $594 per day.

Sailboat Jeanneau Sun Odyssey 509 15.00m  (2013)

From $793 per day.

Oceanis 30.1 REEF  (2021)

From $304 per day.

BENETEAU CYCLADES  (2006)

From $401 per day.

Bavaria Cruiser 40S  (2012)

From $561 per day.

Juanneau Sun Odyssey 43 DS  (2004)

From $448 per day.

OFFER!!!! DAY CHARTER + WATER GAMES!!  (2006)

Private boat sailing tour with Paella!  (2015)

From $449 per day.

Sailboat Sun Odyssey 410 12.00m  (2024)

From $609 per day.

Sailboat Beneteau Cyclades 50.4 15.00m  (2007)

From $671 per day.

Oceanis 40.1  (2021)

From $303 per day.

Bavaria C38  (2022)

From $466 per day, why should i rent a sailboat.

Looking forward to set sail with your sailing boat for a unique escape. Well, a sailboat rental may seem like a fancy choice for a sailing vacation, but it's actually a highly practical option. Sailboats are designed to harness the power of the wind, making them a highly efficient and eco-friendly mode of transportation. Plus, their ability to sail upwind means that you can easily explore coastal destinations that would be more difficult to reach by motorboat.

In addition to their practicality, sailboats also offer a certain sense of elegance and sophistication. There's something romantic about sailing across the water with nothing but the wind to guide you. And with their classic lines and graceful movement, sailboats are sure to turn heads wherever you go.

Sailboat charters offer a unique opportunity for adventure and exploration. Sailing requires a certain level of skill and knowledge, which means that renting a sailboat is more than just a leisurely activity - it's a chance to challenge yourself and learn something new.

With Click&Boat, there are countless sailing destinations to choose from, the possibilities for adventure are truly endless. You can choose to rent a sailboat with a captain if you are new to the sport, or without a captain if you are a seasoned sailor. So are you ready to set sail on a once-in-a-lifetime adventure?

What is the price of renting a sailboat?

When it comes to renting a sailboat, the cost can vary greatly depending on a number of factors. The type of sailboat you choose, the number of guests you will have on board, and the length of the rental are just a few of the factors that can impact the cost. Generally, it is possible to rent a sailboat for less than $100 per day, making it an affordable option for those who want to experience sailing without breaking the bank.

However, for those who are looking for a more luxurious experience, the cost can be much higher. A luxury sailboat can cost $2,100 or more per day. On average, the cost to rent a sailboat is approximately around $450 per day.

It's important to keep in mind that the average price may vary depending on the location you are traveling to, and also on the type of sailing boat. Additionally, if you charter your sailboat with a captain, this will add more to the final price. To get a better understanding of the cost of renting a sailboat, contact local boat owners through Click&Boat's messaging system to find out all the details of the price.

Do I need a boat license to rent a sailboat?

Exploring new countries and islands with a sailing boat charter can be an unforgettable experience, but it's crucial to be aware of the requirements before you set sail. In some countries, possessing a nautical license is mandatory for renting a sailboat, which can be challenging if you're unfamiliar with the process.

For your sailboat rental in Europe , obtaining a nautical license isn't typically necessary. Most countries, including sought-after sailing destinations such as Greece and Croatia , allow boat rentals without special qualifications. Nonetheless, some countries have exceptions, such as Italy , where a certificate of competence is required to rent a sailboat. This can be obtained by taking a sailing course or passing an exam at a sailing school.

If you lack the necessary license or nautical permit, Click&Boat offers the option of renting a sailboat with a captain. 

Where to sail?

The Mediterranean is a perfect destination  for a first-time or advanced sailor. With transparent and calm waters, beautiful beaches, and picturesque coastal towns, the conditions are perfect. Some of the most popular sailing destinations in the Mediterranean include Greece , Croatia , and Italy . There are also tons of small islands and lesser-known beaches that are beautiful hidden places as well.

The Caribbean is also a popular destination for a sailing vacation. With its warm, tropical climate, turquoise waters, and beautiful islands, the Caribbean is a true paradise for sailing enthusiasts. Popular sailing destinations in the Caribbean include the British Virgin Islands , the Grenadines , and the Bahamas .

For those looking for a more remote and adventurous sailing experience, the South Pacific is an excellent choice. The islands of Tahiti , Fiji , and Tonga offer some of the most spectacular sailing destinations in the world, with blue waters, beautiful coral reefs , and stunning scenery. Whether you're an experienced sailor or a beginner, there's something for everyone in the South Pacific .

Our itineraries for sailing destinations:

• Sailboat rental British Virgin Islands
• Sailboat rental Barcelona
• Sailboat rental Ibiza
• Sailboat rental Greece
• Sailboat rental Italy

What brands/models can I rent at Click&Boat?

Click&Boat has a wide range of sailboats for you to rent. Bavaria yachts, with their spacious design, are a great choice for families seeking a sailing experience. Jeanneau sailboats are known for their excellent performance and are great for both racing and cruising.

Beneteau sailboats are designed for easy handling and a comfortable sailing experience, making them great for beginners. Dufours , known for their high-quality and innovative sailboats, are designed for performance and speed.

To narrow down your search, you can use the filters on Click&Boat provided on the left-hand side of the page to select your preferred capacity, size, and power. With these options, finding the perfect sailboat for your needs is a breeze. Once you've found the sailboat of your dreams, simply book it and get ready to set sail.

At Click&Boat, we make it easy for you to find the sailboat that's right for you. With our wide selection of sailboats and user-friendly platform, you're sure to find the perfect vessel for your next adventure on the high seas.

Bareboat Charters

Bareboat charters. your sailboat. your experience.

Sail Away to Tropical Paradise: Explore the Florida Keys on a Well-Equipped Sailing Vacation

Picture this: a gentle breeze brushes against your face as you navigate the calm, turquoise waters of the Florida Keys. You’re at the helm of a beautiful sailing vessel, equipped with all the amenities you need to make your sailing vacation unforgettable. Whether you choose the Catalina 22′ for a day sail or the Morgan 33′ Out Island for an overnight trip, you can rest assured that your boat is well-equipped for your chosen adventure.

As you board your boat, you feel a sense of excitement and freedom wash over you. You’re in charge of your vacation – you get to plot your course and sail into tropical paradise at your own pace. The warm sun beats down on you, and you can’t help but feel grateful for this opportunity to escape the stresses of everyday life.

If you’re planning a multiple night charter, you can provision at one of the local chain supermarkets and enjoy your fully-equipped galley at your leisure. Or, if you’re just renting for the day, you can grab a packed lunch and set off on your adventure.

The Florida Keys offer a plethora of activities for sailors of all levels. From visiting underwater or land-based state and national parks to local beach bars and restaurants, there’s something for everyone. Take a dip in the crystal-clear waters, explore the mangrove islands, or relax on a secluded beach – the choice is yours.

Whether you choose the Catalina 22′, the Morgan 33′ Out Island, or one of our catamarans, you can rest assured that your boat is well-equipped for your chosen adventure. So go ahead, captain your sailing vacation in the Florida Keys and create memories that will last a lifetime.

Meet your yacht at our home in Soper’s Hole

“Know your charter is going to be perfect, without any drama.”

Experience exhilarating Sailing and Nature.

“Discover the Islands of the Florida Keys.”

“Morning Star Charters.”

Let the day Start and stop when and where you desire.

“The Perfect Getaway”

“Enjoy the feeling of being welcomed into the Morning Star sailing family”

Sailing at it’s best

“Morning Star Sailing Charters is the longest established Sailing snorkeling Charter company in the Florida Keys.”

Enjoy self-prepared meals from your well equipped galley while surrounded by incredible beauty

“All the water toys you could want, available to rent right here at Morning Star Charters.”

Morning Star Charters, Sailing, Snorkeling, Kayaking, Sunset Sails, Cottages and Sailboat Rentals in the Florida Keys / Key Largo. Sailing and land based Sailing Vacations.

READY. SET. SAIL THE FLORIDA KEYS

At the end of a 110-mile-long chain of islands, stretched like a string of pearls across a Caribbean blue sea lies charmed Key West, it is here you will find Florida Yachts Charters. We are a boutique yacht charter company that specializes in Bareboat and Crewed Charter, ASA Sailing Instruction and Yacht Management. Experience the best of sailing the Florida Keys with a well maintained fleet of yachts, local knowledge and expertise, a warm island welcome and the personal touches of a luxury yacht charter.

Bareboat Charter

Raise the sails or take the throttle. With a bareboat charter i f you have the experience, then enjoy the freedom of captaining your own yacht on your own Florida Keys adventure. Explore our fleet of sailing monohulls, catamarans and power yachts.

Captained Charter

Sit back, relax, and let the professionals do all the work. Charter the yacht of your choice and connect with one of our experienced crew for your carefree sailing vacation in the Florida Keys. Want a full-service chef, we can help with that too!

Learn to Sail

Let us show you the ropes. Do you dream of owning or bareboat chartering your own sailing yacht one day? We are an accredited ASA Sailing School offering fully private courses for high quality one on one time with your instructor. Customize your itinerary and turn your Florida Keys sailing vacation into a great educational opportunity for you and your family.

Yacht Management

If you are dreaming of enjoying the luxury of keeping your yacht in paradise then join our curated fleet of well maintained charter yachts. We will be happy to consult with you about our yacht management options in the Florida Keys.

6651 Maloney Ave, Unit 1 Key West, FL 33040

[email protected] 800-650-6940

KEEP IN TOUCH

Destination and charter fleet updates, special offers, and more

• Sailing boat rentals

Beneteau - Oceanis 50 | 11 people  (2011)

From $597 per day.

Dufour - Dufour 45 Classic | 12 people  (2002)

From $494 per day.

Hanse - 540e | 10 people  (2008)

From $722 per day.

Jeanneau - Sun Odyssey 410 | 8 people  (2020)

From $636 per day.

Atlantic - 49 | 13 people  (1993)

From $785 per day.

JEANNEAU - SUN ODYSSEY 43' | 8 people  (2001)

From $401 per day.

Beneteau - Oceanis 45 | 10 people  (2013)

From $545 per day.

Dufour - Dufour Gib Sea 43 | 6 people  (2002)

From $471 per day.

Dufour - Dufour 430 Grand Large | 10 people  (2020)

From $481 per day.

Jeanneau - Sun Odyssey 39i | 8 people  (2007)

From $584 per day.

Gibert Marine - Gib Sea 362 | 8 people  (1994)

From $695 per day.

Beneteau - Cyclades 50.5 | 10 people  (2008)

From $1,571 per day.

Jeanneau - Sun Odyssey 410 | 8 people  (2021)

Beneteau - Oceanis 400 | 10 people  (2002)

From $337 per day.

HANSE - 540e | 10 people  (2008)

From $689 per day.

Atlantic - 44 | 10 people  (2004)

From $2,413 per day.

From $681 per day

Jeanneau - Sun Odyssey 440 | 10 people  (2020)

From $407 per day, why should i rent a sailing boat.

A sailing boat is an ideal way to discover new gems on land while cruising on the sea and allowing the wind to carry you. Sailing boats are safe and marvelous boats, which you can use for relaxation, or also for going on an adventure and experiencing the thrill of sailing on the waves.

Spend time with friends or relax with family. Renting a sailing boat can be the best way to make the most of your holiday! Look forward to sunbathing aboard your boat and enjoying a drink or two in the sun. If you’re ever seeking shade then don’t forget you can take a break and relax in your cool cabin below deck.

How much does a sailing boat rental cost?

A sailboat rental has different price ranges depending on the number of cabins, the length, season, the year the boat was built, if it is chartered with or without a skipper, etc. You can rent a sailboat for a day starting from $250 during low season. Bigger sailing yacht rentals with 6 cabins can cost from $11,000 per week. Rent a sailboat for a week during low season for $1,000 per week. Depending on the owner’s listing, there may be different included or additional costs so make sure you read all of the additional costs and options.

Additional options such as air conditioning, power generator, and water toys raise the price. One last thing to take into account is whether or not you will be sleeping on board and if so, how many people will want a cabin or are okay with sleeping in other living spaces? This decision can greatly influence the price.

Do I need a boat license to rent a sailing boat?

A sailboat charter may require a boating license depending on the legislation of the location, where you are going to sail and the boat owner’s listing. Some owners choose to not have their sailing boat for rent available without a license due to risks of damage. For example, in Spain, a permit is only required for those up to 6 meters in length. Meaning you can sail your boat rental in  Barcelona  without worrying about a permit so long as the boat meets regulations.

Don’t have a boating license? Then you should charter a sailboat with a skipper! A professional sailor will help you set sail and make your sailing holidays unforgettable. Your luxury sailing experience is waiting for you! These special offers allow you to learn from the skipper in your own personal sailing school.

What are the best destinations to rent a sailing boat?

Among the possible sailing boat charter destinations,  Cabo San Lucas  is definitely worth mentioning, as well as  the Bahamas and all of its many islands. Other places to visit are the Spanish Balearic Islands, including Mallorca and Ibiza , Mexico , Italy,  and  Caribbean  destinations, such as  Puerto Rico . The best time of year to sail will depend on your destination and the winds in that area. Places in Europe usually have the best sailing conditions in the summer. Don't miss out on our favorite European spots,  Valencia ,  Corfu ,  Cinque Terre , and  Split . If you are planning to go to places in the Caribbean, Mexico, and South America, these are excellent destinations all year round!

With a sailing boat, you can sail between beaches with spectacular scenery and swim in clear turquoise waters, all whilst making the most of the opportunity to captain your very own boat (if you have the required license). Otherwise, a skipper will be available to help you discover new places and make the experience that extra bit special. From your sailboat, you can dive, snorkel, scuba dive, or use a surfboard to discover the most hidden spots! If you’re feeling extra adventurous then why not test the canoe out?!

What should I consider when renting a sailing boat?

Some things that you should consider when renting a sailing boat:

• Dates of travel
• Destination
• Additional charges

The first things to consider when renting a sailing boat are the capacity you will need, the dates of travel, and the destination you want to start your sailing experience in. The capacity is especially important if you are choosing to stay on the boat. The capacity will also depend on if you decide to hire a crew and a skipper. A skipper may be mandatory for your sailing yacht charter if you do not have a valid nautical license. Make sure you count the correct number of people including crew!

There are also additional charges depending on if you want to add certain features for the trip. You may also choose to bring your pet on board! If you choose this option then you will most likely need to pay an extra price per rental.

What is included in a sailing boat charter and what additional expenses can I expect?

Each sailing boat charter has different additional and included costs, so if you are not sure of what costs are included make sure to ask the boat owner of your rental. Included costs can include mooring in the home port, sometimes skippers may be also included.

You can expect different additional expenses depending on the boat owner’s listing. The skipper may be a mandatory cost and included or can be optional and at an additional cost. Skippers normally range from $180 per day. Items such as extra cleaning, pets on board, early boarding, water sports equipment such as paddle surf, snorkeling gear, and more.

How can I rent a sailboat?

Our website offers a wide range of sailing boats, and you can find the one that suits you best by using our filters. For example, you can choose the size of your boat, the number of people that will be with you, the dates of your trip, whether you require a skipper, and much more! Don't forget to check the time and available dates of each sailing boat and don't hesitate to contact the owner if you have any doubts. Prices range from $1,000 per week in low season, and around $10,000 per week in high season for sailing boats required for more people and with more cabins.

What are the most popular brands for sailing boat rentals?

The most popular brands for sailing boat charters are Bavaria and Jeanneau.

How much does it cost to rent a sailboat for a day?

The cost of a sailing boat charter for a day depends on the destination, the capacity, boat features, season and lastly the boat owner’s listing. For example a sailing boat charter in Barcelona costs around $200/day with 6 places in low season and the boat is 6-8m in length. 

How much does it cost to rent a sailboat for a week?

A sailboat rental for a week depends on the destination, capacity of the boat, boat features, season, and the boat owner’s listing. For example, a sailing boat rental in Barcelona costs starting from $2,500/week in low season. The boat listing has a capacity of 10 people and is 40ft in length. A sailing rental in Miami instead can cost from $1,600/week with the boat having a capacity of 6 people and a length of 41ft.

What is included in a sailboat charter and what additional expenses can I expect?

Usually, there is a base price for the charter period and a flat rate for the additional mandatory costs. Pay particular attention here to decide if you want to include only the final cleaning or also add bedding, towels, and an engine for the auxiliary boat. Other costs include mooring fees, of course, which can vary greatly depending on the size of the ship, the port, and the country. For gas and fresh water, you can expect to pay between $150 and $300 per week.

Do you need a license for a sailing boat rental?

If you want to charter a sailboat without a skipper, most countries require a navigation license. In France and the Caribbean, however, you can charter a sailboat without one. The decisive factor in such cases is the "past history sailing experience" of those who wish to charter the sailboat, which is a sheet that details the entire navigational experience of the interested party.

Where to charter a sailboat?

Spain and Italy offer many beautiful sailing spots. Croatia is an ideal place for beginners. For experienced sailors, we recommend chartering a sailboat in Martinique, Seychelles, Greece, or in the Canary Islands. Choose your favorite destination and we will send you an offer!

Can I move to different places with my sailing boat charter?

Yes. A sailboat charter is an excellent and affordable way to spend a holiday at sea discovering different places. You will feel at ease on board and can anchor in quiet bays or explore a new beach or cove every day. If you rent for more than one day you should know that weekly rentals nearly always start on Saturday afternoon and require you to return to the port of origin the following Friday afternoon. The last night is usually spent on board since check-out will take place on Saturday morning around 9 am.

• (305) 223-3488

FEATURED YACHTS

More luxury yacht rentals.

Party Boats

Our fleet of Party Boats come complete with catering & service. Plan your office events or private parties accordingly.

Sport Yachts

Sport Yachts are great for day trips. Excellent for a small party or a day out in the sea.

Motor Yachts

Luxury Motor Yachts are great for long trips on the water but are also available for shorter day trips & events.

Party Catamarans

Party Catamarans are the best vessels for groups seeking a large stable platform to experience cruising,entertainment, catering and water sports under the sun.

Sailing Yachts

Sailing Yachts offer a classic cruising experience with only the sound of the sails in the wind and the ocean in the background.

Bareboat Yachts

Speed Boats

Speed Boats provide a thrilling and power full cruising experience while covering lots of water fast!

Mega Yacht Charters

Mega Yachts are the choice for guest seeking an elite private luxury yacht charter.

Fishing Boats

Fishing Boats are professionally equipped for deep sea fishing and feature local crews who know where to find fish.

CHARTER TESTIMONIALS

Luxury Yacht Rentals, corporate Team Building, creative charters & Events

Our corporate sailing regattas are perfect for folks seeking an interactive sailing experience..

Our friendly and knowledgeable Captains and mates will inspire and instruct individuals of all levels in the basics of sailing and line handling.

Every vessel will assign an honorary Captain who will assist at times our licensed captains at the helm. This great team-building experience will challenge novice and experienced sailors.

Choose from a variety of traditional sailing monohulls and luxury catamarans..

Luxury Yacht Rentals for Any Event

Our friendly and knowledgeable captains and mates will inspire and instruct individuals of all levels in the basics of sailing and line handling. every vessel will assign an honorary captain who will assist at times ou.

Headquartered in Miami, Florida, we offer a wide variety of boats and event planning services including luxury yacht rentals, yacht charters, party boat rentals, speed boat rentals, yacht weddings, catamaran rentals, sailing yacht rentals, bareboat charters, mega yacht charters, private yacht rentals, fishing boat rentals, motor yacht rentals, sport yacht rentals and boat tours in Miami, Miami Beach, Sunny Isles, Aventura, Hollywood, Fort Lauderdale, Pompano Beach, Deerfield Beach, Boca Raton, Delray Beach, Boynton Beach, Lake Worth, West Palm Beach, Bimini and the Bahamas.

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Sailboat Trawlers and Powerboat charters in Florida are the perfect ways to explore the Islands of the Gulf Coast of Florida!   We have a great line of Grand Banks and Krogen Yachts for charter. SW Florida Yacht Charters also has a great selection of Sailboats and Powerboats so you will be able to find the size and type of vessel that meets your cruising needs. If you are an experienced sailor you may want to do a Bareboat Charter . However, we can arrange for a crewed charter with one of our excellent Captains . Southwest Florida Yachts is the best and most complete yacht charter company in the area. The sailing and cruising grounds from Marco Island to Venice on the Gulf of Mexico provide for quiet protected sailing areas or offshore sails. The Fort Myers area is the best place in America for sailboat charters or powerboat charters. With its unspoiled natural beauty and ease of navigation it offers something for everyone, from the experienced sailor or cruiser to the novice sailing enthusiast . Our cruising and sailing area extends from Cape Romano (Marco Island) to the south , to Venice Inlet to the north and includes: Fort Myers, Cape Coral, Sanibel Island, Captiva Island, Boca Grande, Gasparilla Island, Cayo Costa, Useppa Island, Cabbage Key, Pine Island, Naples, Labelle, Clewiston, and Lake Okeechobee. We offer a wide range of sailboats and power yachts for charter including: Grand Banks Trawlers, Krogen, Island Packet Sloops, Island Packet Cutters, Hunter Sloops, and more .

Whether you are planning a Florida family vacation or a romantic tropical getaway for two, our sailboat or powerboat charters may be just what you're looking for. We are celebrating 30 Years of Sailboat and Powerboat Chartering in Florida and know that you will find a sailing charter one of the best vacations you have ever had.

Call today and book your charter then spend your next vacation on the water where you can sail your troubles away!

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Departure date

Trip duration, multiple days (less than 1 week), weekly trip show boats that have weekly prices. most weekly boats outside of the us are available only saturday to saturday., boat length: 5ft -, manufacturer, boat build year: -, weekly trip, price: $ - $, 4 sailboat rentals & charters tampa, fl.

Tampa Bay and St. Petersburg, FL

boating guide

In addition to the best offers we have for boat and yacht charters in Tampa, FL, see also options available for rent in these nearby locations:

• 49 boat rentals in Tampa, FL
• 49 boat rentals in Palmetto Beach, Tampa, FL
• 50 boat rentals in Bayshore Gardens, Tampa, FL
• 49 boat rentals in Westshore, Tampa, FL
• 50 boat rentals in Greater Palm River Point CDC, Tampa, FL
• 45 boat rentals in Greater Carrollwood, FL
• 47 boat rentals in Town N Country Alliance, Tampa, FL
• 50 boat rentals in Riverview, FL
• 46 boat rentals in Brandon, FL
• 45 boat rentals in Tampa Palms, Tampa, FL

Rent a Sailboat Charter in Tampa, Florida on Sailo!

Choosing a sailboat rental in Tampa, FL? Discover Florida by a private sailboat charter in Tampa with Sailo. Enjoy a whole other side of Florida on a Tampa sailboat rental with captain, or skipper yourself if you prefer. Whatever your boating needs, you’ll find the perfect Tampa yacht rental for your sailing trip, you can find the right party boat rental in Tampa for a special event. Enjoy sunset cruises, watersports or fishing trips, or a day out with family and friends for a memorable experience on a Sailo boat.

Our premium fleet of Tampa sailboat charters in Florida

We’ve been asked many times if a sailboat rental in Tampa is a good choice to explore Florida from the water. With more than 4 charters rented every day during the season, our answer is YES, you’re set for an amazing experience when you rent a sailboat in Tampa! Our boats are available with or without captain, with prices starting at $250 per day, depending on the boat type you choose. Browse, find, and book in minutes the best sailboat for you in Tampa, FL!

How to find the right sailboat charter in Tampa, FL?

Wondering how to find the best Tampa sailboat charter for a memorable experience on the water? We have created a set of advanced filters to help you navigate easily our database of Tampa yacht charters and find the one for you. First pick a start date and then choose your trip duration. You can go for an extraordinary of 2, 4 hours or full day experience. Next, select the number of guests, the type of boat and the price range you are comfortable with. The crew filter helps you narrow down the results to the boats with the captain included in the price, or bareboats that you’ll captain yourself. Choose the boat you want in Florida, to view more pics, read description and reviews. Message the owner if you have any questions or continue with your booking request.

How much does it cost to charter a sailboat in Tampa, FL?

Tampa sailboat charters for daily trips are available at an average of $1100 per day. Cheaper sailboat rentals in Tampa, FL (sometimes with no captain included) may be rented for $600. Our Tampa luxury yacht charters may have price tags up to $6500, with crew, fuel, docking fees and other extras added to your budget.

What happens in case of bad weather?

For captained charters, weather cancellations and reschedulings are entirely at the discretion of the Captain or Boat Owner. The Renter can not invoke 'bad weather' and request a refund as reason for cancellation unless the Captain or the Boat Owner agrees to it. For captained charter, the Captain will make the decision if the weather conditions are dangerous to get out on the water. Cloudy skies or a slight chance of rain are not grounds for cancellation or rescheduling. If a cancellation or rescheduling due to bad weather is necessary, either the Renter or the Boat Owner must send an email to  [email protected]  stating the reason. If the Renter sends such a request, the email must include a written confirmation from the Boat Owner. Read more details  here .

Because we love the ocean

Sailing is a great way to experience nature. So we like to remind everyone that keeping nature as beautiful as possible involves a little effort from all of us. Some of our tips for responsible boating include:

• Don’t litter or throw waste overboard - take rubbish home and dispose of it responsibly
• Eco-friendly sunblock can help prevent damage to marine life
• buy local and sustainable food products

However long you’re sailing for, a little goes a long way.  Read more about responsible boating.

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