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    Destin Sailing Adventures

    Destin Sailing Adventures

    4.5 • 27 reviews
    Fort Walton Beach, FL

    Glide across Destin’s emerald waters aboard a sleek Stiletto 27 catamaran captained by lifelong adventurer Kip. Backed by 15 years of racing and charter experience, he welcomes just six guests at a time, crafting laid-back outings...

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    Book Destin Sailing Adventures

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    Proposal & Anniversary Sailing Cruise in Fort Walton Beach

    Sail with a licensed captain for a proposal or anniversary cruise

    $482.30
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    Cruise To Crab Island In Destin Private Charter

    Cruise to Crab Island with a licensed captain, music, shade, and room to relax

    From$482
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    Sunset Catamaran Adventure

    Sail at sunset on a catamaran with time to spot marine life and relax on the water

    $482.30
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    Sunrise Sailing Charter in Destin

    Sail Choctawhatchee Bay at dawn for Mid Bay Bridge views

    $344.50
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    Snorkel Cruise in Destin & Choctawhatchee Bay

    Snorkel Destin and Choctawhatchee Bay on a captain-led boat charter

    From$482
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    Cruise Santa Rosa Island on a Private Sailboat Charter

    Sail Santa Rosa Island on a private charter with a licensed captain

    From$482
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    Cruise Fort Walton Beach on a Dolphin Tour

    Cruise the Emerald Coast with a licensed captain to spot dolphins

    From$482
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    2-Hour Catamaran Sailing Cruise in Fort Walton Beach

    Sail Choctawhatchee Bay on a 2-hour catamaran adventure

    $371

    Review summary

    4.5
    Excellent
    27 reviews•Google Maps
    22
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    Captain Kip and Elizabeth have clearly mastered the art of making guests feel special on the water. With a perfect 5-star track record, reviewers consistently praise their friendly, knowledgeable approach and the relaxed atmosphere they create. These are private charters on a 27-foot catamaran that seats up to six, so you get an intimate experience perfect for families or small groups. Guests love lounging on beanbag chairs under sail power, enjoying the peace without motor noise. Dolphin sightings are a frequent highlight, and several reviews mention stops at Crab Island for swimming and snorkeling. The captains clearly know where to find wildlife and the best spots to explore. Families with kids rave about how welcoming and patient both hosts are, and the experience has even served as the backdrop for a successful proposal during a sunrise cruise. Multiple guests called it the highlight of their vacation, citing everything from sunset cruises to mid-morning sails as relaxing, fun, and memorable ways to experience the Destin waters.

    What people are saying

    Review 1 of 3
    5/5

    Well-stocked bait shop and knowledgeable staff.

    Photo of Sam & Heather Perry

    Sam & Heather Perry

    April 21, 2026

    Review 1 of 1
    5/5

    Well-stocked bait shop and knowledgeable staff.

    Photo of Sam & Heather Perry

    Sam & Heather Perry

    April 21, 2026