catamaran rides florida

Catamaran Sailing Vacations in Florida Keys: Upper and Lower Florida Keys - Dry Tortugas - Fort Lauderdale, Miami, Marathon and many different stops along the way! Charter a Catamaran with no crew and drive yourself or hire professional crew for your catamaran trip.

The florida keys have become a popular destination for americans looking for a tropical sailing vacation without leaving their own country. the florida keys can be considered the american caribbean and features all the same amenities as other island destinations such as world class sport fishing, scuba diving and snorkeling, boating, sailing, kayaking and eco-tours. each of the island destinations has some special features. we invite you to visit each area individually and discover the tropical paradise in the florida keys..

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Florida Keys Itinerary

Keys - one week.

Upper Florida Keys - 3 Days

Lower Florida Keys - One Week*

Sailing from Marathon Key you will experience the many pleasures and sites of the Florida Keys. The unspoiled coral reefs of the Lower Keys have many sites where you can tie up to a mooring ball and snorkel or dive. Hawks Channel provides fantastic sailing, as there is protection from the ocean swells but still great wind.

Dry Tortugas - One Week*

Bahamas itinerary, chain in the bahamas.

Across the Gulf Steam from Florida's east coast lies the Bimini Island Chain. These sub tropical low-lying islands are a fantastic destination for a weeklong sail. Bimini offers some of the finest SCUBA diving, snorkeling, fishing and beachcombing anywhere. These "islands in the stream" offer water clarity, which is nothing less than spectacular. You may rent snorkel gear at our office in Ft. Lauderdale if you have not brought your own. For those who are certified divers we recommend renting your SCUBA gear from Underseas Sports in Ft. Lauderdale before you head across the Gulf Stream.

The Bimini Chain is lightly populated with the center of village life located on North Bimini, in Alice Town. There are many small restaurants, shops, and bars, as well as the Hemingway Museum at the complete Angler. Marinas are abundant if you decide not to anchor out. The beaches on North Bimini offer miles of un-crowded fine white sand and snorkeling from the waters edge. Golf Carts and Mopeds are available for rent so you can explore the island. One of the most interesting dive and snorkel sites off of North Bimini is "Bimini Road", which some say is the ruin of the lost city of Atlantis.

South Bimini is primarily residential with only two marinas. The new Bimini Sands Marina is located at the entrance to the harbor and has a Customs and Immigration office so you can clear in there without having to take a taxi and ferry over to North Bimini. The other marina is located at the south end of the island. A new channel has been dredged in Nixon's Harbor that takes you into the marina. Not far from the south end of South Bimini lies the wreck of the "Sappona". This is a great snorkel and dive site.

The only other island in the Bimini's with a marina is on North Cat Cay. This is a private Island with some "high profile" homeowners. For this reason the local authorities limit the accessibility of the island for non-members. You are welcome at the Marina for transient dockage but they prefer for you to stay in the area of the marina where there is a fine dining restaurant a store for provisions, dock bar, and gift shop. It is a truly beautiful setting at the marina and we recommend this for your last night in the Bahamas. Just off the coast of South Cat Cay is a fantastic dive site. "Tuna Alley" has mooring balls and is 50' to 80' with deep caverns and crevasses in the coral.

There are many other Anchorages such as Honeymoon Harbour, Dollar Harbour. Moxom Rocks, and Nixon Harbour. Please call to speak with our knowledgeable staff for more details.

One Week Itinerary to the Bimini Islands

Day three -, day seven -, day eight -.

Obviously there can be a lot of variation on this itinerary, but it shows there is plenty to do in a week charter to the Bimini Island Chain. If you would like further information or would like to plan a different Bahamas trip give us a call and speak with our knowledgeable staff. We can provide you with a cruising guide to the Bahamas Islands as well as charts of the area.

Tropical Sailing

Catamaran tours in miami & fort lauderdale, florida, our most popular trips.

• User All ages
• Hour Glass 2.5 Hours

Full Moon Sunset Sail Ft. Lauderdale

Join us as we cruise along the Intracoastal waterway, you’ll be treated to a tour of the magnificent waterfront mansions and spectacular yachts.

• Most popular
• Hour Glass 2 Hours

Sunset Cruise Castaway the Day – Fort Lauderdale

A perfect way to end the day, taking in the breathtaking views. This Fort Lauderdale sunset cruise calls for sun dresses, sandals and chilled wine. Take advantage of one of Florida’s finest highlights upon our comfortable catamaran as we sail out to the Atlantic Ocean.

Sunset Cruise Castaway the Day – Miami

Castaway the Day Sunset Cruise is a perfect way to end the day, cruising on the Caribbean Spirit. This Miami sunset cruise calls for sun dresses, flowered shirts, sandals, and cold refreshments.

• Hour Glass 3.5 Hours

Sail and Splash – Fort Lauderdale

Come sail and play in Fort Lauderdale’s “Aquatic Playground” on this unforgettable excursion aboard our state of the art catamaran the Spirit of Lauderdale. Sit back, relax and enjoy one of the best Fort Lauderdale boat cruises .

• Hour Glass 3 hours

Island Adventure – Miami

Enjoy an unforgettable adventure at our island destination during our day cruise from Miami. Experience the Miami lifestyle like a local on board our motor catamaran, Tranquility.

Looking for more to do? Check out these other local tours!

• Hour Glass 1 Hour

Waverunner Beach Rentals

Aloha watersports.

An excellent water sport activity for the whole family!

Seven Isles of Fort Lauderdale Tour

Blue moon outdoor center.

A sightseeing tour of the Seven Isles of Fort Lauderdale!

Kayak and SUP Rentals

2 hour – all day rentals! Choose between a single or tandem kayak, or a stand up paddleboard.

• Hour Glass 45 Min

Speedboat Tour

Thriller miami speedboat adventures.

The Thriller Speedboat Tour departs from Bayside Marketplace in Downtown Miami, Florida. The tour provides the ultimate sightseeing experience in true “Miami Vice Style”.

• Hour Glass 1.5 Hours

Parasailing

Sea rocket water adventures - ft. lauderdale.

Get ready to fly high above the Gold Coast and have a first class experience you will remember forever!

Everglades Day Safari

The Everglades Day Safari offers an in-depth, naturalist-guided day trip into the majestic Everglades! Includes an airboat ride, nature walk, mangrove wilderness boat ride and a delicious lunch!

What we do at Tropical Sailing

We offer two convenient locations Miami Marina at Bayside and Bahia Mar Resort in Fort Lauderdale providing great sailing access to South Florida’s finest destinations.

Our sailing and power vessels are Catamarans, that by nature of the design, provide a stable, comfortable platform with plenty of lounging space for your guests.

Our experienced staff consists of licensed Coast Guard Certified Master Captains and first mates certified in first aid and rescue. Every Captain and crew member has been hand picked for their exceptional skills and personality. Our entire staff consisting of charter specialists, captains, crew and mechanics share a passion for South Florida’s waterways, working on the water and sharing their enthusiasm with everyone they come in contact with.

During your trip, a professionally trained captain and crew will pamper your guests with tailor-made service while you cruise the world’s most desirable Caribbean destinations. Special menus can be arranged, transportation coordinated – everything necessary to assure an adventure that your group will remember for a long, long time!

Discover the ultimate in extravagance and personalized service as you step aboard our luxury crewed yachts. Stylish, spacious and elegant, our prestigious catamaran will delight you. Equipped to the highest standards, with special features and state-of-the-art electronic and water sports equipment, you can expect quality similar to that of a luxury five-star hotel.

We look forward to sharing our love of sailing and water sports with you, your family and your friends!

See Why We're Highly Rated!

Absolutely amazing! Cannot recommend this enough! We got to see dolphins, jumping fish, the sunset, and sit with our legs on the net of the catamaran. I can’t recommend this enough! It should be an especially part of anyone’s Ft. Lauderdale vacation!

Captain E and Nick were great on this tour! We brought our grandkids and they were very attentive to them! We all had a wonderful time! We would highly recently this sunset tour! Beautiful views and great crew!

Great time with Captain E and Nick! Absolutely worth doing, especially on a hot June night! Will book again on our next Ft. Lauderdale trip.

This is hands down a must if you have a family with kids!!! Captain Joe and Danny were amazing and we all had the best time. Super accommodating and helpful and made the whole sail from start to finish a great experience! Don’t hesitate to book this excursion you won’t regret it. The price was perfection for the experience you got.

One of the best romantic dates I could ever imagine. They sailed us out in the Miami Bay (Biscayne Bay) and we got to watch the sunset. Wow! A clear 5/5

Crew on board was amazing and indulged with the participants on board. They gave great knowledge of the houses and the city in general! The cruise was relaxing and calming all together I would definitely recommend!

Beautiful views, helpful, accommodating and entertaining crew and a nice long route all made for a great value trip

• Crab Island Adventure
• Snorkel Adventure
• Sunrise Sail
• Sunset Adventure
• Dolphin Adventure
• Santa Rosa Islands
• Proposal/Anniversary
• Fireworks Adventure
• Photo Gallery
• Current Weather
• Wind Forecast
• Local Regattas
• Surf Forecast
• Sailor Slang
• What makes a good sailor?
• The Ocean Race

Exclusive Catamaran Sailing Adventures

Spring break 2024.

Mins Minutes

Secs Seconds

Come explore the majestic waters of the Emerald Coast!

Catamaran sailing in the emerald coast sun..

Are you visiting the Destin, Okaloosa Island, Navarre Beach area and needing a little adventure in your life? This is what you're looking for aboard catamaran Destin Sailing Adventures. The boat is a Stiletto 27 Special Edition Catamaran, designed to provide maximum sailing pleasure and performance over a wide range of wind and sea conditions. Made for adventure and racing, so it offers plenty of excitement and comfort for any occasion. The boat is outfitted with a 20hp motor, so if the wind isn't blowing we can still get out and play! Charter comes with a local captain to take you to all the local spots, while you sit back and relax.   

We offer an array of private tours, cruises, and adventures at a reasonable price. The longer you book the more fun you can have and the more money you’ll save. These are private charters, so you won’t be with a huge crowd during these unprecedented Covid 19 times. Just you and the people you bring. Come explore Crab Island, Sunset cruises, Sailing lessons, Dolphin Tour, Snorkeling, Marriage Proposals, Birthdays, sightseeing tours, Anniversary celebrations, and more with us today.    

We are dedicated to making sure you have a great time while visiting the Emerald Coast. All trips include up to 6 Guests, Licensed Captain, cooler with ice, bean bag chairs, sound system, and a head (bathroom). Our Captain has 15 years of local experience racing/sailing along the Gulf Coast of Florida and more! Please contact us for special requests such as sailing to Navarre Beach (Juana's Sailors Grill), Sandestin (Baytown Wharf),Etc. Some of the best catamaran sailing adventures Destin, Okaloosa Island, Santa Rosa Island has to offer!

Jetty East Snorkeling

Usually one of the busiest spots during the summer, so book your trip early to beat the crowds.

Snorkeling with a Manatee.

Early bird got the manatee this day!  

Spanish Mack

Up close and personal to a Spanish Mack doing its thing!

Pick up location

Adventure marina, okaloosa island.

1201A Miracle Strip Pkwy SE, Fort Walton Beach, FL 32548, USA

850-217-3448

"A ship is always safe at the shore, but that is not what it is built for."

Albert Einstein

Destin Sailing Adventures

1201B Miracle Strip Pkwy SE, Fort Walton Beach, Florida 32548, United States

Copyright © 2023 Destin Sailing Adventures - All Rights Reserved

AFTERNOON SUN SAIL

Life is better on the water... Come sail with us!

Adults - $60 / Children under 12 - $30

A 2 hour Sailing excursion lay back, relax, sip a delicious cold drink from our service bar and listen to a variety of music. Custom built 50 foot Catamaran. Spacious sundeck. loads of space to view. Abundant seating area. Convenient service bar Two restrooms Beer and Wine Licence Stereo Sound System Capacity 41 guests

There is no better way to sail the Gulf of Mexico waters than aboard the Kai Lani Catamaran!

View Booking Info and Availability

Arrive early for check in

DAILY SUNSET CRUISES

The perfect way to end your day or kickoff your night!

• Relaxing Sunset Sail Monday & Friday $60 for adults $30 for children (under 12)
• Sunset Sail with Live Music Tuesday, Thursday & Saturday $75 Adults and $30 for children (under 12)
• Sangria Sunday Sunset Cruise Sunday Evening $80 Adults and includes bottomless Sangria $30 Children (under 12)

Enjoy a 2 hour Sunset Sail in the Gulf of Mexico or Clearwater Bay. Whether you choose to have a few drinks and make new friends dancing to live music or enjoy a wonderful romantic cruise with that special someone, we know you'll make a memory to last a lifetime.

SPECIAL EVENT CRUISES

Join us for one of our monthly special event cruises

Our monthly event cruises feature an open bar, food and may also have live music. Many of these cruises are also partnered with non-profit organizations to increase awareness or funds. So raise a glass with your friends while helping the community!

Just some of our special events include our Valentine's day Sunset Cruise, Easter Brunch Cruise and July 4th Celebration Sail

We also have all inclusive packages available at discounted rates. These packages include other goodies like party favors for your bachelor or bachelorette party or decorations and special touches for your birthday or reunion celebration.

Please include in your email a phone number in the contact form below so one of our representatives can be in touch with you.

Contact Us for Pricing and Availability

Where are you located?

Where do i park, what about bad weather, can we bring our own alcohol, are guests required to wear life jackets, is there a restroom on the boat, what is the unlimited drink wristband, how do i pay for drinks on board if i don't have a wristband, can i host a private party on the boat.

It is best to reserve as early as possible, as last minute bookings are hard to get. We suggest a few days ahead of time. Walk-ups are welcome if you want to leave your adventure to chance of available space on one of our day trips.

Contact Info

Address 25 Causeway Blvd, Slip #49 Clearwater Beach, FL 33767

Phone (727) 446-6778

@kailanicat1 on Facebook

@kailanicatamaran on Instagram

Reservation and Charter Policies

© 2024 Kai Lani

Sightseeing Marco Island and Naples on our boat tours.

Off the hook adventures., private sightseeing., daily boat tours & sunset cruises., we only offer private tours real estate showings, our catamaran has open fresh air with a forward seating and a shaded back deck with bench seating., we provide a chilled cooler with bottled water bring anything additional., lounge in the fresh sunshine or sit in the shade and enjoy refreshing fresh gulf coast air., private just your group, up to 6 passengers maximum per, catamaran boat tour .   , offering 2 hour tours completed within 2.5 hours or double 4 hour tours completed within 4.5 hours., all tours are private for up to 6 passengers on the catamaran, with a 50% deposit  2 hour, or reserve our longer double 4 hour boat tours., our rates include sales tax, shell bags and free refreshments., this is a fun activity when visiting marco island or naples. , reservations for our, catamaran boat tours.  , for catamaran sightseeing  , reservation boat tour times. , click 👆on, boat tour and or sunset cruise,, for current weekly and daily availability., we have been sailing from marco island as off the hook adventures  for 20 years. , all our tours are private for 2 – 6 of only your passenger guests per catamaran.  , a fun thing to do on your marco island and naples florida beach vacation., our boats are comfortable, fun and safe for all ages., enjoy local knowledge and narration by an experienced  licensed captain. , 🏝 explore uninhabited island beaches and sandbar shorelines for sea shells 🐚 . , watch for dolphins, manatees, birds and other seasonal wildlife. 🐬, your adventure awaits….

Showing all 1 result

Private Marco Island boat tour reservations $350/$550

Use code BAREFOOT for 10% off Guided Tours!

Catamaran Cruises in Key West, FL

Escape the downtown crowd - cruise with billy.

Key West’s nautical history is all based on its proximity to the world’s 3rd largest living coral reef. From pirates and privateers to ship wreckers and fisherman the draw has always been the sanctuary provided by the Florida Great Barrier Reef.  Key West’s coral rock islands trace a contiguous pathway from the Atlantic Ocean & Gulf of Mexico intersect all the way to mainland Florida. To this day our primary industry, tourism, celebrates our unique natural ecosystem in the shadow of the reef. 

Whether you want to cruise a couple of hours, island-hop all day, or see our beautiful wildlife, Billy has you covered! Bring your reef-safe sunscreen, and we’ll take care of the rest!

Ticketed Tours

• Kid Friendly!
• Users All ages
• Info Up to 36 people
• Clock 3.5 hours

Dolphin Watch & Snorkel Tour

Search for wild dolphins in their natural habitat and snorkel Key West’s backcountry waters off the Seabreeze!

• Most Popular Cruise
• Info Up To 38 People
• Clock 2 hours

Key West Sunset Harbor Cruise

Take in a breathtaking Key West sunset on this harbor cruise that sails past the southernmost point of the U.S. and cruises by a Civil War Fort.

Private Experiences

• Our Newest Boat
• Info 1-6 People
• Clock 2 to 8 hours

Barefoot Private Charters

Create the perfect outing for up to 6 with a custom charter! Cast off from the island and explore the unique nature surrounding the Florida Keys!

• Info 1 to 40 people
• Clock 3 Hours

Morning Island Charter

Spend your morning at the sandbar and experience the turquoise waters surrounding Key West at a slower pace on this private charter.

• Clock Varies

Seabreeze Charters

Snorkel, see Dolphin, or visit a sandbar with an open-air cruise for up to 40 people. Create the perfect escape with a private adventure aboard our 45-foot Corinthian catamaran!

• Sarasota & Siesta Key
• Longboat Key
• Anna Maria Island
• Clean Water

Captain Jambo's

Destin .

Call Now! 850-888-8FLY

AS FEATURED IN...

 Catamaran Sailing Cruise Destin, Florida

FALL & WINTER

AVAILABILITY

Click the Book Online Button for Schedule

The Closest

Check Out Our Latest Dolphin Sighting

Private sailing charters of destin, fl.

The STILETTO catamaran sailboat has plenty of room for up to 6 passengers, so bring your friends and family. Let's take your group on a Destin sailing adventure to make memories that will last a lifetime!

Snorkeling gear is complimentary and the sailboat is equipped with a lavatory, iced cooler and wifi stereo to play your tunes! The 30-foot catamaran boasts plenty of room for up to 6 people with two areas hang out on: the rear deck with shaded seating and trampoline in front. The catamaran sailboat is designed with two hulls that create a stable, non-rocking experience. So let's raise the jib (front sail), and let the sailing fun begin!

Bring snacks, lunch, romantic dinner, or water toys, we have your snorkel equipment and life jackets covered. Remember, it's your private trip so have fun your way!

Best of all, you can tour the Destin Harbor on your way out to see the unique waterways of Destin while you head out to the Gulf to look for dolphins, snorkel deep and shallow spots, Crab Island to hang out, or Okaloosa Island to look for shells! Parking is available at Heron Harbor and check-in directly on the boat at the dock! Complete instructions and tips will be sent to your phone after booking. We are happy to answer any questions! (850)888-8359

Destin Sailboat Tours

Combine any of these activities for your, sailing adventure, destin sunset cruise.

Wind in the sails, your honey at your hip, a majestic Destin sunset on the horizon... what else could your vacation need?  Destin sunset cruises are not only great for couples, but the whole family too!

We offer marriage proposal cruises of Destin, FL ! Book your trip, and surprise your love with a private engagement sail of Destin.

Snorkeling Destin's Emerald Waves

If the kids want to snorkel, Captain Jambo's has you covered. Masks, fins and snorkels are provided free for adults and kids. Explore the jetties and grassbeds. For the more adventurous, take a sail out to the Gulf to dive down to see starfish, angelfish and more! Destin boasts many great spots to explore the tropical fish or dive for sand dollars! Take our GoPro camera with to capture your snorkeling adventure!

Look for Destin's Dolphins

Dolphin sightings are pretty much a guarantee when sailing in Destin, Florida. Our local pod is quite friendly! Don't fight the crowds on larger boats. Enjoy your up-close-and-personal dolphin experience, the most ecological way! And if the area permits, you may jump in for a swim. It's your sailing Destin vacation! See how close the dolphins are in our latest video!

Learn to Sail Destin

Come out on an afternoon trip when the wind is pumping and we can push the Stiletto Catamaran to the limit through the Destin waterways. You will not believe how fast you can sail on a catamaran sailboat! Get ready to pull some ropes, Captain Billy has over 25 years of experience on boats and can help you learn to sail Destin, Florida!

Hang Out on Crab Island

For the folks that want to check out the local scene, a stop at Destin's famous Crab Island, won't disappoint! At this beautiful, clear, waste-deep sandbar, you may watch the sights or get involved in the fun. There are floating restaurants and bars, music, as well as activities for the kids!

Look for our Crab Island Sailing Tour that combines snorkeling, shelling and Crab Island fun on our booking page. Private and individual rates available.

Fireworks Cruise of Destin Harbor

Catamaran Tours

3-Hour Trip                $450

4-Hour Trip                $600

5-Hour Trip                $750

All Day, 6 Hours           $875

Sunset Sail 2-Hr           $375

Sunset Sail 3-Hr           $500  Fireworks Cruise 1.5-Hr   $375

(Thursdays, May 28 - Sept 3)

Sunset/Fireworks 3.5-hr   $600

One night a week Destin has a fireworks display over the harbor! Come out Thursday nights for a spectacular display while cruising in the sailboat. The deck of the catamaran is perfect for having fun with friends and family, there are two benches and a front trampoline for watching the explosions! Check out our Facebook page for video of the show!

Bring libations, snacks, dinner, whatever you need to make your Destin fireworks cruise take off! And don't forget your favorite streaming or MP3 tunes to hang out and make the festivities your own. Add a beautiful Florida sunset to your fireworks cruise for an amazing night! (3.5 hour booking)

Price is for up to 6 people with experienced captain as guide. Gratuity excluded.

Catamaran holds up to 6 passengers per Coast Guard regulations.

Ice-filled chest provided. Just bring drinks & snacks! (BYOB!)

Book with confidence! We reschedule or issue a refund for inclement weather (winds >20mph or rain), so book with a day or two as an alternate when possible.

Credit card fee on all credit purchases. Cash for best price.

Learn More About Our Catamaran Sailboat!

What's so great about a catamaran? A catamaran denotes a boat with two hulls or compartments that enable the vessel to displace water evenly on both sides. This design allows the catamaran to avoid rocking, as a traditional, single-hulled sailboat does. For folks on vacation--this point is a gold nugget--those that are not accustomed to boats tend to get seasick.

Why the double-hull design is a vacationers best boat friend:

Stable, non-rocking design . Why is this important? Because as the hull heaves so may your stomach.

Plenty of storage space with 2 hulls . And, if the kids fight, we can separate them.

Speed. The catamaran is twice as fast as a traditional sailboat. Save the monohull for the land turtles! (Sea turtles are fast too.)

Light footprint. A Stiletto can maneuver in shallow water due to a broader displacement of water across two lightweight hulls (Crab Island, here we come!)

Built for comfort. You aren't awkwardly lounging on a sloping deck like a monohull sailboat.

Maximized deck space. The catamaran has two opposing benches with cushions, as well as 80 square feet of trampoline for lounging and watching the waves.

Stiletto Catamaran

If you are thinking of chartering just any ol' catamaran, let me tell you why the Stiletto brand makes this boat even groovier:

Built light for speed. Although you may want to relax on your Destin sailing cruise, never forget, this cat has speed in its back pocket. The catamaran tops out at 25 knots (20 mph). In Destin, we can safely cruise at 15 knots with the jib (front sail) raised, and feel the power.

It will never sink . Aeronautic technology is utilized in its honey comb laminate that enables the material itself to float, not relying on the intact body of the vessel. So, no matter what the Florida waters bring, this puppy floats.

Versatility of design. You can beach it; you can trailor it. When was the last time you saw a monohull sailboat pulled up on the beach or roaming down the highway? This boat goes everywhere. But watch out, you might catch catamaran fever thinking of the possibilities of where you could take it!

You are cool by proxy. Riding in our Stiletto catamaran brings you closer to the lastest version of the Stiletto XF, the foiling catamaran that once it reaches 14 knots, raises up and rides on hydrofoils, appearing to hover 2 feet above the water!

The "Best Day Ever" Sailboat Cruise, 4-6 Hour Private Charter

At Captain Jambo's, We Know How To "Do" Destin.

Here is a write-up of a much loved itinerary that

may save you from being one of the many people

who ride into the dock thinking, "I wish I had

longer on the sailboat!"

The sails are set due south from Captain Jambo's

peaceful, scenic bay dock. With tummies full of

butterflies and expectations, we sail through the

glowing, emerald waves, under the Destin Bridge,

through the Destin Pass, and East and West Jetties to the magnificent Gulf of Mexico. Here, we look for bottlenose dolphins, sea turtles, and other marine life. We sail along Florida's beaches, marveling at the beauty of the water and sugar white beach. Next, the sails are set north, back through the Destin Pass to the world famous, Crab Island. This shallow, clear sandbar is a hot spot for Destin boaters' fun in the sun. Catch a margarita or some fish tacos at the festive Waterworld Restaurant and Bar. Play with the kids on the giant, inflatable waterpark. Just remember, no babysitting your pontoon boat, come and go as you please to check out the festivities, your captain will be happy to hold the anchor! After you've had your fill of Crab lsland, we sail to the nearby grassbeds for snorkeling. Crabs and fish abound here. You might even spot a majestic seahorse! Take our underwater Gro Pro camera to document your adventure! Next door is one of the few areas to find seashells in Destin, so take some souvenirs home from your hunt. When your pockets are full, we will set sails again for a relaxing sail through the calm waters of the Choctawhatchee Bay, watching the explosive

colors of the sunset on this

incredible sailing day.

Finally, we head back to

the dock from where our

adventure began. Now,

the sailboat sails away,

leaving you sun-kissed

and ocean-drunk with a

mind full of memories of

an amazing Destin sail.

​ Captain Jambo's Destin Harbor is happy to serve neighboring areas that may not offer our one-of-a-kind sailing tours, such as Sandestin and Hwy 30A Florida vacation destinations. Let us help you put together a vacation package to explore Florida by sea! Look below to see how far you are from our location:

East of Destin

Sandestin 20 min

Santa Rosa Beach, Florida 32 min

Blue Mountain Beach, Florida 36 min

Grayton Beach, Florida 39 min

Seaside, Florida 40 min

Watercolor, Florida 40 min

Seagrove, Florida 41 min

Rosemary Beach, Florida, 48 min

West of Destin

Fort Walton Beach, Florida 12 min

Navarre, Florida 36 min

Looking for Things To Do in

Sandestin, hwy 30a, or fort walton beach, 850-888-8fly.

Captain Jambo's Sailing Tours

Heron Harbor

314 Harbor Blvd

Destin, FL 32541

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Learn how to easily plan your dream trip to Florida!

14 Best Boat Tours In Naples Florida (Sunset, Catamaran, Dolphin, and more!)

March 18, 2021 //  by  Florida Trippers

The best Naples boat tours are waiting for you! If you’re looking for a new way to take to the water, you’ve come to the right place.

Florida’s West Coast beaches are undoubtedly beautiful, but swimming off the shoreline and sunbathing can get boring. If you’ve ever wondered what’s beyond the shoreline, then these Naples boat tours are for you. This is truly one of the best things to do in Naples!

It doesn’t matter your disposition, there’s a boat tour from Naples for everyone! If you want to relax and take in the scenery, no problem. Or if you want a workout and want to kayak through the Ten Thousand Islands or the Everglades, there’s a tour for you!

There are even options for Spring Breakers too! Say goodbye to getting stuck on sandbars or worrying about DUIs. Naples boat tours have an option for you that takes away all the worry and hassle so you can be safe!

So no matter if you’re a tourist, a local, a vacationer, a fisherman, or somebody who just wants more of the great out doors? There’s a boat tour from Naples just for you. We even have a list of the best Everglades tours from Naples if you want an airboat ride. Discover what Southwest Florida has to offer you!

14 Best Boat Tours In Naples Florida (Sunset, Airboat, Dolphin, and more!)

Ten thousand islands boat tour.

For half a day, board a boat and explore one of Florida’s top natural attractions. This tour is one of the most fun Naples boat tours, exploring the Ten Thousand Island!

You’ll depart from Marco Island , about fifteen minutes south of Naples, with 12 other people to ensure an intimate experience. Then you’ll head to a small barrier island only accessible by boat on tour lasting about 3 hours.

The captain will point out sea life, highlight interesting sites, and discuss local history and ecology. While on the island, you’ll be able to swim, go snorkeling , and look for rare seashells!

Book Now : Ten Thousand Islands Boat Tour

Western Everglades Adventure Tour

One of the best Naples boat trips is to explore the ecosystem that is the Everglades . This tour will take you from Naples into the marshes and swamps of this natural wonder.

While you ride, you’ll be looking for native Florida wildlife like birds and turtles. You’ll even see alligators , of which there are more here than anywhere else in the world!

There’s even an interactive reptile show at the end of the day! You’ll spend a half-day on the water with your naturalist guide who will teach you about the ecosystem while you spot herons, egrets, and snakes!

Book Now : Western Everglades Adventure Tour

Cape Romano Boat Tour

For a quaint morning and afternoon on the water, enjoy one of the best Naples boat tours of Cape Romano! With a guide, you’ll explore one of the prettiest areas of the Ten Thousand Islands.

You’ll depart at 9 AM from Caxambas Park Marina at the south end of Marco Island, only 15 minutes away from Naples. The tour only hosts 10 people, so you’re in for an intimate experience.

You’ll learn about the region’s marine life and see the ecosystem of mangroves of the Ten Thousand Islands. Afterward, you’ll stop on one of the islands to go shelling ! Make sure to look out for the Florida Domes !

Book Now : Cape Romano Boat Tour

Ten Thousand Islands Catamaran Tour

On this Naples boat tour hosted by Backwater Adventure , you’ll be in the captain’s seat! As you go through the Ten Thousand Islands, you’ll be operating your own catamaran!

On the morning of your tour, you’ll meet at the Little Bar Restaurant. You’ll be provided with all the required US Coast Guard equipment and bottled water. Complimentary pictures will even be shared with you via Dropbox!

Choose from a 2.5-hour or 5-hour tour, and you will operate your own 2 person catamaran through the waterways of the Ten Thousand Islands. Led by a guide on a separate catamaran, you’ll be able to see the marine life at a closeness not available on other boat tours from Naples!

Book Now : Backwater Adventure

Naples Bay and the Gulf Eco-Boat Tour

Of all the Naples boat tours, this may be the most luxurious. You’ll privately be led on a 3-hour sightseeing/eco-tour to discover Naples’s vibrant ecosystem.

Either departing at 9 PM or 1 PM, you’ll spend 3 hours on a 22-inch motorboat with comfortable seating for all guests! Shade will be provided by a T-Top plus an additional bimini on very hot days.

As you head head north through Naples Bay, you’ll see dolphins, manatees, and a variety of birds including blue herons, roseate spoonbills, ospreys, and egrets!

You’ll be provided with complimentary bottled waters and sodas as well as a cooler with ice for your personal snacks and drinks. You can bring your own alcohol onboard and be provided with cups and a corkscrew! Don’t forget a Bluetooth radio to stream music of your choice!

Book Now : Naples Bay and the Gulf Eco-Boat Tour

Naples Sightseeing Boat Tour

Take a break from the hustle and bustle of life on one of the best Naples boat tours. This cruise will help you discover the top sights that Naples has to offer!

You’ll board a small motorboat where you’ll be able to purchase alcoholic beverages and small snacks. Make sure to bring your camera to take unobstructed pictures of the city.

After stopping at Tin City, a shopping and dining destination, you’ll cruise to the Gordon River Greenway. Along this stretch of water, you’ll see historic buildings and the homes of millionaires in Port Royal, some even owned by celebrity snowbirds!

Book Now : Naples Sightseeing Boat Tour

Dolphin, Birding and Shelling Tour

On one of the best Naples boat tours, you’ll be introduced to birding! You’ll also have the opportunity to see dolphins and then go shelling for rare shells on the Ten Thousand Islands.

These tours are never “canned,” meaning the course changes daily to find the most beautiful Florida wildlife as it migrates. You’ll learn about these species in detail and their ecosystems from an experienced naturalist guide!

You’ll be able to see many different species depending on the season. Expect to encounter manatees, dolphins, sea turtles, bald eagles, ospreys, herons, egrets, pelicans, and roseate spoonbills. You’ll also see many species of fish and shore birds.

Make sure to bring your own water and snacks to last 2 hours. Wear a sunhat, sunglasses, sunscreen, and shoes you don’t mind getting wet. You also won’t regret bringing a camera and a pair of binoculars!

Book Now: Dolphin, Birding, and Shelling Tour

Sunset Catamaran Sailing Excursion

How many Naples boat tours allow you to sail on a catamaran named “Cool Beans?” Cool Beans Cruises will be the perfect way to see Southwest, Florida to make lasting memories.

Choose between a 2.45-hour day-sail or a 2.5-hour champagne sunset cruise! With up to 20 passengers, you’ll depart from Naples and pass by the Rookery Bay National Estuarine Wildlife Reserve.

During the day-sail, you’ll stop by Keywaydin Island for shelling and swimming. Keep your eyes peeled for dolphins, birds, and manatees ! Bring a camera to capture a photo!

On the sunset sail, you’ll have a complimentary champagne toast right as the sun sets on the water. On both cruises, you’ll be able to drink complimentary soda, water, beer, and white wine.

Book Now : Cool Beans Cruises

Mangrove Tunnel Kayak Eco Tour

Kayaking in Florida is always beautiful, but you can experience the best of one of the most fun Naples boat tours! Here , you’ll paddle a kayak through the mangroves of the Everglades.

You’ll discover the exotic beauty of the Everglades’ mangroves forest with the expertise of an experienced guide and naturalist. You’ll spend three hours winding through sleepy creeks and mangrove canopies.

Don’t worry if you’re not an experienced paddler, you’ll learn kayaking techniques from your guide. You’ll also get a larger-than-life view of alligators, herons, ducks, and loads of fish species! Don’t forget the bug spray!

Book Now : Mangrove Tunnel Kayak Eco Tour

Marco Island Dolphin-Watching Tour

Hosted by Florida Adventures and Rentals, this is one of the most relaxing of the Naples boat tours. Traveling through the Ten Thousand Islands, you’ll be looking for dolphins.

With your captain-guide, Captain Steve , you’ll explore the Ten Thousand Islands after departing from Marco Island at 11:30 AM. You’ll only be with 10 other travelers, so it’s an intimate experience.

You’ll be able to see dolphins right up close to the boat! Captain Steve will educate you about the natural environment and the area’s ecosystem. Also be on the lookout for native birds as well as fish in the maze of mangroves.

Book Now : Marco Island Dolphin-Watching Tour

Ten Thousand Island Jet Ski Eco-Tour

When you need to beat the heat, one of the regular Naples boat tours just won’t cut it. To get the best views on the water and from the water, consider the Ten Thousand Island Jet Ski tour !

Take a break from the beach and fly through the waters of the Ten Thousand Islands on a jet ski. From the Naples marina, your guide will point out dolphins and sea creatures often missed by untrained eyes.

Because you’re on a jet ski, you’ll be able to travel to secluded locations on the 30+ mile route that are inaccessible to boats and kayaks. With a small group size, you’ll be able to travel to the Florida Domes as well!

Keep in mind to drive a jet ski, you will have to obtain a Boaters Safety Certificate. You also must be 16 years old to operate the machine. If you were born before January 1, 1988, you do not need any certificate at all!

Book Now : Ten Thousand Island Jet Ski Eco-Tour

Naples Deep Sea Fishing Tour

Anglers, rejoice! Sometimes the pier just doesn’t cut it. Instead of chartering your own boat and going it alone, take one of the best Naples boat tours to go deep-sea fishing !

Departing from the Cocohatchee River Park Marina, you won’t even need your own fishing license on this chartered boat. You’ll drop anchor about 10 miles or 16 kilometers offshore before you cast your lines.

Choose between a 4-, 6-, or 8-hour tour. After you depart at 7 AM, your captain will offer instruction and casting lessons to those who need it. Equipment will be provided. Depending on the season, you might find cobia, mackerel, snapper, and grouper!

Book Now : Naples Deep Sea Fishing Tour

Captain Party Hard Boat Tour

If you’re looking for a fun and different Spring Break destination , consider taking the most fun of the Naples boat tours out there: The Captain Party Hard Boat Tour !

Captain Party Hard will provide you a safe and worry-free boat tour. Departing from Marco Island, you’ll sail around Keywaydin Island and the Ten Thousand Island with multiple opportunities to spy on dolphins.

You’ll be surrounded by great music and a party atmosphere on a 27′ Hurricane Deck Boat. For four hours, you won’t have to worry about DUIs or getting stuck on sandbars.

You’ll be provided with beach chairs, games, beverages, and snacks. Dance with locals on the beaches, too! All you need is a bathing suit and a towel! Captain Brent Wilson provides the rest.

Book Now : Captain Party Hard Boat Tour

Guided Kayak Tour

If sitting on a boat sounds unappealing, then enjoy the water on one of the most adventurous Naples boat tours! With small groups of 6 maximum guests, you’ll be on an intimate kayaking adventure !

Small groups create the best opportunity to quietly kayak so everyone can see as much wildlife as possible. Your naturalist guide will provide information about the incredible flora and fauna of Southwest Florida.

Departing from the Cocohatchee River Park Marina in Naples, your guide will provide you with your equipment: kayak, paddle, life vest, and even a dry bag for your electronics. Bring your own water, sunblock, and bug spray.

After departure, you’ll head to Barefoot Beach Preserve. Through the mangroves, you’ll have the opportunity to see dolphins, manatees, birds, and more! Then you’ll stop by Barefoot Beach to stretch your legs and go shelling and swim!

Book Now : Guided Kayak Tour

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