sailboat cruises naples fl

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Take a Virtual Journey with Cool Beans

Choose a day-sail, champagne sunset or a private catamaran cruise below to enjoy a sailing adventure aboard our 42 foot sailing catamaran, Cool Beans .

If you’re looking for something different we can explore Keewaydin Island or one of the many other hidden treasures aboard Lil’ Beans , our luxury pontoon.

Day-Sail Cruise

Price includes a delightful escape to the beautiful waters of the Gulf of Mexico. Relax and enjoy your sailing experience on our beautiful catamaran while watching the abundant sea life and native birds of Southwest Florida.

During our day sails, we do stop for approximately 35 minutes at one of the many beautiful beaches of Southwest Florida – Keeywaydin Island, a barrier island in South Naples to swim, explore , and collect shells.

(Please note stopping at the beach is based on weather conditions. If it is too rough/choppy in the Gulf, the Captain may choose not to include a stop at the beach. Also know that to get to shore, you must swim in. We drop anchor in approx. 6 feet of water, approx. 30 yards off shore. Life jackets and floaties provided if needed. You are also welcome to stay on the boat to soak in the sun and scenery during the stop if you do not want to swim.)

• Complementary – soda, water, beer and chardonnay included
• You can also bring aboard additional food/snacks and beverages (no red wine please) on-board. Due to insurance liability, hard liquor is not allowed on our vessels.
• Smoking and Vaping are prohibited.

Gratuity Extra

Please note: 18% Gratuity will be added for parties of 7 or more.

• * Children must be at least two-years old.
• ** 24 hour prior notice cancellation policy for parties of 6 or under
• *** 48 hour prior notice cancellation policy for parties of 7 or more

Champagne Sunset Cruise

See Southwest Florida the way it was meant to be seen . . . by water! Escape from the crowds and set sail to take in our beautiful sunset. Sit back and enjoy a warm breeze in your face, a glass of champagne in your hand and the view of one of the most beautiful sunsets you will ever experience. Sail back to port and marvel at the view of the Gulf of Mexico and Naples/Marco Island beaches with the sunset lighting your way.

• Complementary – soda, water, beer and chardonnay included
• Complementary glass of champagne at sunset

Private Day-Sail or Sunset Cruise

 Would you like to have the boat to yourselves? Booking a “Private Cruise” is the perfect way to celebrate any occasion while enjoying your privacy. Choose from one of our Day Sails or our Champagne Sunset Cruises and leave the rest to us. Price includes items described above for your specific choice of cruise.

• ** 48 hour prior notice cancellation policy

Lil’ Beans Pontoon Island Beach and Sunset Adventures

Enjoy a Private 2 ½ hour Luxury Pontoon Tour for Up to 6 Guests for our Day Excursions or a 2 hour Sunset Excursion. Our Pontoons are perfect for Island hopping, up close Eco/Nature and Shelling on Keeywaydin Island. A “Must Do” while visiting SW Florida! (Sunset Charter arrives back to dock approximately 15 minutes after Sunset)

Keewaydin Island– A Deserted Barrier Island

Keewaydin Island is an 8 mile long unabridged barrier island just to the north of Marco. A fantastic sandy beach stretching the length of the island, with great shelling and opportunities to see plenty of wildlife. It serves as a sanctuary for wildlife and a popular recreational destination, especially at weekends. Keewaydin provides a great opportunity to experience Florida’s natural coast and is a vital nesting ground for Least Terns and Loggerhead Sea Turtles.

Hide-A-Way Beach/Sand Dollar Island – An Unspoiled Gulf Beach

Located just north of Tigertail Beach you’ll find Sand Dollar Island which abounds with wonderful seashells and is absolutely breathtaking and totally natural. Many of Florida’s beach-nesting shorebirds that face conservation challenges can be regularly spotted on Sand Dollar, including the Snowy Plover, Least Tern, Black Skimmer, American Oyster Catcher, and Wilson’s Plover.

• GOOD FOR CHARTERS COMPLETED BY AUGUST 31 st , 2024
• * Price includes soda and water
• ** Children must be at least two-years old
• *** 48 hour prior notice cancellation policy

Groups & Special Occasions

Small intimate sunset weddings.

Make memories to cherish for a lifetime when you exchange wedding vows during your Cool Beans private sunset sail. Whether you have something particular in mind or need ideas, we can provide some wonderful options to assure that your wedding is everything you expect and more.

Romantic Sailing Excursions

Create the perfect moment to ask your significant other for their hand in marriage with a private cruise along the beautiful waters of Southwest Florida. Ask us how we can help to make your interlude aboard the Cool Beans a magical event to treasure for a lifetime.

Private Anniversary Cruise Celebrations

Reaffirm your love for one another alone or among special friends and loved ones aboard the Cool Beans. Your private sailing excursion is sure to be fun, romantic and memorable.

The Ultimate Birthday Private Cruise

Making a magical birthday celebration aboard the Cool Beans is one of our specialties. Whether your event is for a family daytime cruise, adventure among friends or a private sunset intimate sail, we are here to make your birthday cruise an event to remember.

Bachelorette Party

What a great way to celebrate the Bride to Be with her “Last Sail Before the Veil!” Specializing in small groups up to 20, booking a Bachelorette Party with Cool Beans Cruises will truly create a lasting memory..

Share the gift of a Cool Beans Cruise!

239-571-7716

Boatnaples.com.

An Extraordinary Experience Awaits You On The Water Customize a unique and memorable tour. Relax while your captain takes you on a private guided tour of the Gulf of Mexico and the Inter-coastal waterways of Naples, Bonita Springs, Estero, or Fort Myers. Explore the backwaters, Ride out into the Gulf and travel along the beach, watch for dolphins and the beautiful birds of Florida. See the magnificent homes from the water, view incredible sunrises, sunsets. Come aboard, enjoy the magnificent waterways and create your own unforgettable memories !

SUNRISE/SUNSET CRUISES – COASTAL AND BACKWATER 

ECO-TOURS, BEACH PICNICS,  SHELLING,  AND DOLPHIN WATCHING

 DOG FRIENDLY

 Departing daily Sunrise through Sunset

 Cocohatchee River Marina

 USCG Licensed and Insured

Sunset Cruise

Backwater Home Tour followed by Sunset - 90 Minutes

2 Hour Day Tour

Backwater and Coastal Tours - Dolphin Watching

4 Hour Sun and Fun

Dolphin and Bird Watching - Beach and Backwater Home Tour

Trip to Fort Myers

6 Hours - For All Ages - Up to 6 Passengers

Parasailing

Starting at $100 per person | Up to an Hour Long Duration | Ages 6+

Jet Ski Dolphin Tour

Highly Recommended | 2 Hour Guided Tour | From $200 | Ages 6+

Book Your Trip Today!

Reserve your adventure today! Your Captain is ready for you at BOATNAPLES.COM. Located in North Naples at Wiggins pass, the Cocohatchee River park Marina. Start your journey with ease and explore the beautiful waters of South West Florida with us.

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Experience the Best Boat Tours in Naples

Top-rated boat tour in naples, florida.

Sit back, relax, and pop the cork of your favorite wine on our guided boat tour while cruising through the canals and backwaters of ultra-luxurious Port Royal and Naples or to the secluded Keeywaydin Island.

Private Sunset & Dinner Cruise

On our sunset cruise, you and your group will be taken to the absolute best locations to watch the sun dip below the ocean’s horizon. The setting of our sunset tour is relaxing, quiet, and romantic for private two-person trips. Order your takeout from any restaurant in Naples, including the Syren, Nosh, or Bonefish Grill. Guests should order directly from the restaurants by phone or in person. Food choices can be brought to the boat. Dinner, flatware, and wine glasses are provided on the boat.

Keewaydin Beach Adventure

This secluded island is layered with pristine shells that lay untouched from the general public. We provide beach chairs, umbrellas, water, and ice. Feel free to bring takeout aboard from your favorite restaurant or sandwiches from Publix (we don’t provide food). We will escort you through the mangroves and canals for a beautiful calm ride directly from Naples at the footsteps of a beautiful resort. This is a shared boat that holds up to 6 guests (coast guard rules, not ours.). We bring our garbage back along with anything else as there are no facilities on the island. No Bathrooms, No Garbage Cans. We leave nature the way we find it. There are plenty of shells to collect, and some days food and ice cream visit the island via food pontoons.

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Board Our Boat To Learn All About Naples

Your tour Captain will highlight the houses of celebrities and politicians, historical landmarks, and fun facts about the area and wildlife. We can provide as much of a tour as you would like, or sit back and enjoy a peaceful time with your family or significant other.

Naples Boat Tour

We’re located at the Naples Bay Resort 1500 Fifth Avenue South Naples, Florida 34102

If you’re looking for private boat tours in Naples, look no further. All private tours, including sunset cruises, for up to six people for only $750. Your group will enjoy our unforgettable adventure throughout the luxurious canals of Naples & Port Royal.

Naples' Premier Sailing Charter Company

bareboat/ boat club 

Island Sailing - Naples, FL​​

​Captained charters

We offer many different captained private sailing adventures, including 2, 3, or 4-hour sunset sails and day sails, overnight/weekend trips, and week-long adventures along Florida's southwest coast, Florida Keys, or to the Bahamas. Enjoy a bay tour, set sail in the gulf, and enjoy what nature has to offer aboard Island Time (47' Beneteau) or Island Dreams (31' Catalina). Be on the lookout for dolphins and various FL birds! We cater to our customers' every need and strive to provide our customers with the very best service possible.  Let your captain be your tour guide on your private charter. 

Experienced sailors can bareboat  Island Dreams , our 31' Catalina, for a half day or full day sail. Enjoy cruising along Naples' sugar white sandy beaches aboard a fun and easy-to-sail yacht. She is well equipped for your sailing needs.  Want to go sailing but don't want to pay the high costs of owning a sailboat? You can! We also offer a boat club (5 and 10-day packages). 

discover more >

Island Sailing Naples | 800 12th Avenue South, Naples, FL | [email protected] | 239.398.1483

< CLICK HERE FOR OUR CURRENT SPECIALS >

• Captained Charters
• Bareboat/Boat Club
• Our Captains

• 239-734-0670

Naples Florida

Why Go Bar Hopping When You Can Hop On A Bar?!

What better way to spend a day than hopping aboard your own byob tiki bar, tiki fun tours for adults*, (*teens 13 & up may accompany parent or guardian*), bring your own beverages & snacks, launch location for naples changed in june of 2022, naples launch is from the boathouse on naples bay restaurant.

Cruisin Tikis Naples

What better way to spend a day on the water than hopping aboard your own byob bar for your cruisin tiki® tour boat charter., learn more about our captains, check out the fun visit our photo gallery, learn more before booking a tour, certified in tiki fun.

• Up to 6 Passengers Per Tiki
• Shared Tiki or Private Tours
• U.S.C.G. Certified Captain
• Captains Tiki Fun Certified
• All Required Safety Gear
• 2 Tikis in Naples
• 1 Tiki in Bonita
• View Rates - Click Here
• Bluetooth Stereo System
• Cooler With Ice

Customer Reviews

Stephanie C

Legal Notice - Cruisin' Tikis is a patented, copyrighted and registered trademarked vessel. Our "Trade Dress" is proprietary and may not be duplicated in whole or part without specific written approval of Cruisin' Tikis International, Inc.

Fun Things to do in Naples, Florida: From the Beaches to the Everglades

N aples, on the Paradise Coast of Southwest Florida, is a popular destination for both winter snowbirds and vacationers. There are many reasons why — this stylish and upscale community offers great restaurants and shopping in a sophisticated downtown, plus beautiful beaches and top-rated golf courses.

Whether you love to get out on the water or the links, there are things to do in Naples Florida for everyone including arts, culture, and fun annual events like the world-famous Swamp Buggy Races, Naples Craft Beer Fest, the Stone Crab Festival, and the Naples Bay Christmas Boat Parade.

While it is busy year round, Naples really bustles from December through April. We have visited in both summer and winter, and rounded up some of the best things to do in Naples Florida.

Things to do in Naples, Florida

Naples pier.

The central hang out spot, and the best place to catch a sunset, is at the famous Naples Pier. Parking can be tight so if you want to park at the pay lot near the Pier you should get there early in the day. Otherwise, you can likely find street parking on 5th Street and walk over.

You don’t need to pay to access the Pier, and fishing off the pier is allowed without a permit. There are even sinks and stations for cleaning your catch. Even if you don’t fish, it is fun to take a walk to the end to watch the pelicans diving for their meal. You may even luck out and see some dolphins. Just stake out your spot early if you are going for sunset.

Lowdermilk Park

While there is a beach at the Naples Pier, it is narrow and a little crowded. If you aren’t staying at a beachfront resort, another great option is Lowdermilk Park . While you need to pay by the spot to park, access to the beach is free. You can also rent chairs and umbrellas on the beach.

The beach is lovely and the park offers a concession stand, showers, restrooms, picnic tables, two children’s playgrounds, and even beach volleyball.

Pure Florida Boat Cruise

If you want to go fishing, take a dolphin cruise, ride on a jet boat, rent jet skis, or even take a shelling eco-tour, Pure Florida is the place to look. Boats leave out of the historic Tin City shopping district so you can grab a lunch of Stone Crab claws before heading out or a drink when you return.

If you want to get out on the water but also get up close and personal with wildlife and nature, consider a kayak tour with Rising Tide Explorers . This is Southwest Florida’s only biologist owned and operated adventure company.

They offer kayak rentals, kayak tours, and boat tour with biologists. These tours go into winding mangrove tunnels, a bird rookery island, ancient sand dunes, and you can even go shelling on a remote section of Keewaydin Island.

If you love to shop, you are in luck in Naples. There are many pockets of places with great shopping, from planned centers to parts of downtown Naples. Each has its own unique personality.

Tin City is a historic area that reminds us a lot of Fisherman’s Wharf in San Francisco or Seattle, but on a smaller scale. You will find restaurants, specialty shops, and a mix of kitschy souvenir stores.

For upscale waterfront shopping, The Village at Venetian Bay, offers a mix of boutiques and familiar brand names, combined with a number of indoor and outdoor waterfront dining options.

The main shopping districts downtown are found along 5th Avenue South and 3rd Street South. These streets are also lined with a mix of great restaurants, many of which offer indoor and outdoor seating. On 3rd Street South you will find Tommy Bahama and upscale boutiques selling your fill of Lily Pulitzer. Fifth Avenue South also offers boutiques, art galleries, and restaurants.

A kid pleaser is the Naples Zoo at Caribbean Gardens. This accredited zoo is home to animals like lions, giraffes, monkeys, pythons, and bears. You can also book an animal encounter with lemurs, honey badgers, anteaters, and giraffes.

Naples Botanical Garden

The Naples Botanical Garden covers 170 acres and is home to plants from around the world. The Gardens also offers fun annual events like Night Lights (Christmastime), April Foolin’ in the Garden, and Garden Nights.

When we were there in December, our plan was to attend the Night Lights and we bought tickets in advance (as recommended since it sells out), but unfortunately it was pouring rain. While the event is rain or shine, we decided we would rather not get drenched!

Corkscrew Swamp Sanctuary

Remember a few years ago when there was that YouTube video circulating of a panther running past a person on a boardwalk in Florida? Well that was at the Corkscrew Swamp Sanctuary. Don’t worry, that isn’t a common event.

Located about 30 minutes east of Naples, Corkscrew Swamp Sanctuary is home to alligators, otters, deer, turtles, and obviously panthers! You can walk into the Everglades ecosystem on the 2.5 mile boardwalk through flat woods, wet prairie, and into the largest old growth Bald Cypress forest in North America. 

Airboat Tours

If you are willing to travel a little further south into the Everglades, there are plenty of opportunities for airboat tours in Everglades City and beyond. We decided to try a 30-minute tour with Wooten’s Everglades airboat tours.

These tours go through the mangroves and grasslands, with a high likelihood of spotting alligators. They also offer a 30-minute Swamp Buggy Tour that brings you through the river of grass of the Everglades. 

Extend Your Stay

Want to combine a stay in Naples with other nearby destinations? Check out our recommendations for the best Florida Gulf Coast vacations or here are some ideas.

Marco Island

Just 30-45 minutes south of Naples is the vacation paradise of Marco Island. You will find everything from high rise hotels to beach houses. There are similar things to do in Marco Island , but I’m a little partial to the wide white sand beach on Marco Island.

Sanibel & Captiva

Just 30-45 minutes to the south, outside of Fort Myers, the wildlife refuge on Captiva and the amazing shelling on Sanibel are a great draw for nature lovers.

Perhaps you want to move from the quieter West Coast to the cultural hot spot of South Florida’s east coast — Miami and Miami Beach. There is so much to do in Miami from food tours and art walks to people watching on South Beach and visiting world-class museums. Miami is just a two hour drive away across Alligator Alley.

There is even a seasonal ferry from Marco Island to Key West, making this hot spot accessible from the West Coast of Florida without the otherwise 7+ hour Florida Keys road trip .

Where to Stay in Naples

Note: This post contains affiliate links. If you click a link and make a purchase, I may receive a small commission at no cost to you.

Naples Grande Beach Resort

If you are looking for an upscale stay, we enjoyed our stay at the Naples Grande Beach Resort . Just keep in mind that if prefer the beach over the pool, you will need to walk a long boardwalk to get to the beach or take a golf cart shuttle. Don’t worry though, it is worth it as the beach is beautiful.

Residence Inn by Marriott

On our recent stay, we needed something a little more moderate so we chose to stay off the beach in the centrally located Residence Inn by Marriott . We were able to use points for a spacious two-bedroom suite and our stay included a buffet breakfast and the hotel had a decent pool for a Residence Inn.

Where to Eat in Naples

Naples is a great destination for foodies, especially sea food lovers. There are great brunch spots like Jane’s on 3rd, as well as delicious dinner options. See my list of recommendations for where to eat in Naples .

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The post Fun Things to do in Naples, Florida: From the Beaches to the Everglades appeared first on We3Travel .

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