Free Concierge Service
    Text or call 1-877-GREET-WELL
    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

    Resources

    • Travel Guides
    • Experience Gift Cards
    • Help Center
    [email protected]1-877-GREET-WELL

    Safe & Secure Payments

    © 2026 Greetwell, Inc. All rights reserved.
    Privacy PolicyTerms
    Cruise Destin Bay

    Cruise Destin Bay

    5.0 • 124 reviews
    Destin, FL

    Cruise Destin Bay offers intimate, six-passenger pontoon adventures through Destin Harbor, Choctawhatchee Bay, and the emerald waters of Crab Island. Led by Captain Harry, a U.S. Coast Guard–licensed captain with decades of experi...

    Report an issue

    Book Cruise Destin Bay

    Addon image

    Sunset Cruise in Destin Harbor & Choctawhatchee Bay

    Cruise Destin Harbor at sunset on a small-group pontoon

    From$67person
    Addon image

    Destin 22' Pontoon Cruise

    Cruise Destin Harbor and Choctawhatchee Bay with your own captain

    From$67person
    Addon image

    Cruise to Crab Island Sandbar From Destin

    Float and swim at Crab Island on a 3-hour private pontoon charter

    From$84person

    Review summary

    5.0
    Excellent
    124 reviews•Google Maps
    108
    0
    0
    0
    0

    Captain Harry and his wife Lesli have built something genuinely special here. Guests consistently describe them as warm, knowledgeable, and safety-focused, with many noting it feels more like spending the day with friends than a commercial tour. Harry's a certified Merchant Marine captain who clearly knows these waters inside and out. Multiple reviewers mention his keen eye for spotting dolphins and his ability to position the boat for incredible wildlife encounters. The intimate group size (up to 6 people) gets praised repeatedly for making the experience feel personal rather than crowded. The trips to Crab Island come loaded with equipment—paddle boards, floating mats, chairs, snorkel gear, and even speakers—so you can just bring your food and drinks and enjoy. What really stands out though is Harry's attention to safety and genuine care for people. Several reviews describe him rescuing another family caught in a dangerous current, and guests were moved by his quick thinking and humanity. Whether weather turns the sunset cruise foggy or rain interrupts your afternoon, this couple adapts gracefully and keeps the experience enjoyable. Return customers are common, with some booking multiple trips during a single vacation.

    What people are saying

    Review 1 of 5
    5/5

    The best afternoon trip to crab island! Captain Harry was highly experienced and navigated the crowds with ease. He was goofy and made the ride out and back in very fun and entertaining. Captain Harry genuinely wants everyone to have a good time and be prepared for everything - he even helped me get over my fear of touching the jellyfish! Floats and paddle boards were available for use and the pontoon was clean and comfortable. Absolutely worth your money if you’re heading to crab island - book with Captain Harry!! I will definitely be a returning customer :)

    Photo of Jewels Riley

    Jewels Riley

    September 2, 2026

    Review 1 of 1
    5/5

    The best afternoon trip to crab island! Captain Harry was highly experienced and navigated the crowds with ease. He was goofy and made the ride out and back in very fun and entertaining. Captain Harry genuinely wants everyone to have a good time and be prepared for everything - he even helped me get over my fear of touching the jellyfish! Floats and paddle boards were available for use and the pontoon was clean and comfortable. Absolutely worth your money if you’re heading to crab island - book with Captain Harry!! I will definitely be a returning customer :)

    Photo of Jewels Riley

    Jewels Riley

    September 2, 2026