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best way to get engaged in destin, florida

Destin Sunset Cruise

Give her the most memorable wedding proposal on your Destin vacation! Imagine you take your honey for a walk, stumble upon a stately, white sailboat, and step aboard. Wisked away with surprise, she is delighted. Then, you anticipate the special moment, pop the question, and celebrate with entangled bodies of potent love and champagne in hand. It's just the two of you! The rest is a history of love.


Destin, Florida, is home to an amazing natural harbor, picturesque sugar-white beaches, and glowing emerald water. Our Stiletto catamaran showcases all of these amazing elements for your once-in-a lifetime moment! No worries of seasickness with the stable, double-hull design and plenty of room to dine on our cushioned deck or snuggle on the front trampoline with a glass of wine for some breathtaking views. Our captain Billy knows how to be hospitable and will photograph the occasion with your camera, or he may photograph your proposal with his professional Nikon camera and give you an SD card of digital photos capturing the proposal and sail! ($50)

  • What can you expect from this experience?

    This romantic wedding proposal/engagement sail includes:


    • 2–6 hour use of a 30-foot catamaran sailboat
    • One seasoned Coast Guard licensed captain with exemplary hosting capabilities
    • Free planning of a cruise
    • You may drop off or we will pick up special items (so she won't wonder why you are trekking around with a bag of goodies).
    • Ice-filled cooler
    • Bluetooth-enabled stereo with an MP3 player
    • Life jackets
    • Lavatory

    Exclusions:


    • Towels, if swimming
    • Gratuity
    • True love (please bring it with you!)
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a romantic outing

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 for the whole family too! We offer marriage proposal cruises to Destin, FL! Book your trip and surprise your love with a private engagement sail to Destin.

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an extraordinary adventure

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 you to capture your snorkeling adventure!

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make some new aquatic friends

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!

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acquire a new skill

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!

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join the party

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, and 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 are available.

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a beautiful display

Fireworks Cruise of Destin Harbor

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 videos of the show!


Bring libations, snacks, dinner, or 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)

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The whole package

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

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 beaches. 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 in 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 land, 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 sail again for a relaxing sail through the calm waters of Choctawhatchee Bay, watching the explosive colors of the sunset on this incredible sailing day. Finally, we head back to the dock, 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.

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Parasailing

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