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Sailing Destin - Family Fun - Sunset Sail Destin

 Catamaran Sailing Cruise
Destin, Florida



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The Closest



Green sea turtle Destin.jpg
Destin Sailboat Cruise FL

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

Catamaran Sailboat, Sailing in Destin, Florida
Deck of the Cataman Sailboat, Sailing Destin Florida

Destin Sailboat Tours

Combine any of these activities for your
Sailing Adventure!
Destin Sunset Cruise
Destin Sailing.jpg

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
Snorkeling Sailing Destin Florida

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 cruise Destin - Destin Florida Sailboat

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
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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
Sailing Destin FL Crab Island
Crab Island Sailing Destin, FL

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
Destin, Florida Fireworks Sailing

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 honeycomb 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!

Catamaran Sailboat

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?


Captain Jambo's Sailing Tours

Heron Harbor

314 Harbor Blvd

Destin, FL 32541

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