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Destin's Most Romantic Thing To Do -- A Private Sailboat Charter

Destin Marriage Proposal Engagement Sailboat Cruise

Engagement & Romantic Cruises


Best Way to Get Engaged in Destin, Florida

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, champagne in hand. It's just the two of you! The rest is a history of love.

The Setting: Destin, Florida


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)

Marriage Proposal Destin Ideas
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The Engagement Cruise

This romantic wedding proposal/engagement sail includes:

  • 2-6 hour use of 30-foot catamaran sailboat

  • One seasoned, Coast Guard licensed captain with exemplary hosting capabilities

  • Free planning of cruise

  • You may drop-off or we will pick-up of special items (so she won't wonder why you are treking around with a bag of goodies)

  • Ice-filled cooler

  • Bluetooth-enabled stereo with MP3 player

  • Life jackets

  • Lavatory


  • Towels, if swimming

  • Gratuity

  • True love (please bring with you!)

Check out our sailing page for more information on pricing and options for day or evening sails, activities, and fireworks availability!

Engagement Destin Florida Catamaran Sailboat Charter

Captain Jambo's Destin Sailing Tours

314 Harbor Blvd

Destin, FL

(850) 888-8359


"I'm not a rich guy but this trip made me look like a millionaire to my now wife! And to think I thought the group dinner cruise was my only option for a romantic boat proposal!"

Chad A./ Milwaukee, WI

"Weeks later, I still hear her tell the story of how we 'just barged on someone's boat,' before she realized this was our engagement trip"

Ted A./ Topeka, KS

"The sailboat was such an amazing place for our engagement. It really allowed us to spend that time together in Destin. I wouldn't change a thing!I love you Amanada!!"

Brian P./ Austin, TX

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