We're here to help
    Book online or call (650) 414-7338
    Ask AIAI
    Ask AIAI
    Why travelers choose Greetwell

    Curated by our team

    Every experience is hand selected and approved by Greetwell.

    Personal concierge

    Real humans available to help before, during, and after your booking.

    Intimate & authentic

    Including unique in-home experiences you won't find anywhere else.

    Easy booking & cancellation

    Reserve in minutes with free cancellation on most experiences.

    Greetwell

    Experiences that stay with you long after the trip

    Greetwell curates authentic local experiences and provides personal concierge support in over 500 destinations, helping you explore confidently wherever you go.

    About

    • Our Story
    • For Experience Providers
    • For Hospitality Partners
    • For Developers

    Concierge Support

    • Help Center
    concierge@greetwell.com(650) 414-7338

    Safe & Secure Payments

    © 2026 Greetwell, Inc. All rights reserved.
    Privacy PolicyTerms

    Destin Sailing Adventures

    5.0 • 58 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...

    Report an issue

    Book Destin Sailing Adventures

    Addon image

    Sunset Catamaran Adventure

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

    $482.30
    Addon image

    Sunrise Catamaran Sail in Destin

    Catch sunrise views over Choctawhatchee Bay with a private captain

    $344.50
    Addon image

    Destin and Choctawhatchee Bay Snorkeling Adventure

    See local sea life as you snorkel Destin and Choctawhatchee Bay with a licensed captain

    From$482
    Addon image

    Santa Rosa Island Adventure

    Sail with a licensed captain to swim, snorkel, and unwind—perfect for families and groups up to six

    From$482
    Addon image

    Emerald Coast Dolphin Adventure Tour

    Spot dolphins, seabirds, and sea turtles with a licensed local captain

    From$482
    Addon image

    2-Hour Sailing Adventure on Choctawhatchee Bay

    Sail Choctawhatchee Bay with a captain, spot wildlife, and try steering the catamaran

    $371

    Review summary

    5.0
    Excellent
    58 reviews•Google Maps

    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 5
    5/5

    Captain Kip and Elizabeth were nothing short of amazing. They were patient, kind, and knowledgeable. Thank you so much for having us.

    Photo of Jessica Cardin

    Jessica Cardin

    July 28, 2025

    Review 1 of 1
    5/5

    Captain Kip and Elizabeth were nothing short of amazing. They were patient, kind, and knowledgeable. Thank you so much for having us.

    Photo of Jessica Cardin

    Jessica Cardin

    July 28, 2025