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    1. Local experiences/
    2. Things to do in Fort Walton Beach…/
    3. Water Activities/
    4. Sailing/
    5. Santa Rosa Island Adventure
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    Santa Rosa Island Adventure

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

    5.0 stars• 58 reviews
    From$426

    Duration

    3–9 hrs

    Ideal For

    Up to 6 people

    Includes

    Captain, Snorkel gear, Cooler

    Highlights

    Set sail for Santa Rosa Island with a licensed captain aboard a Stiletto 27 Special Edition. Enjoy bird gazing, swimming, and a relaxing sail; snorkeling is available on trips of 3 hours or more.

    • Choose from 3 to 9 hour charters
    • Sail on an insured Stiletto 27 Special Edition
    • Swim and snorkel on trips of 3 hours or more
    • Lounge on bean bag chairs under a sunshade
    • Play your music on the onboard sound system
    • Keep drinks cold in the provided iced cooler

    What's Included

    • Licensed local Captain
    • Insured Stiletto 27 Special Edition
    • Snorkel gear
    • Bean bag chairs
    • Sound system
    • Life vests
    • Cooler with ice
    • Sunshade
    • First aid kit
    • Portable Head (aka toilet)
    • Hand sanitizer

    Things to know

    Charter accommodates up to 6 passengers. Swimming and snorkeling are available on adventures of 3 hours or more.

    Cancellation Policy

    Free cancellation up to 24 hours before arrival. No refunds within 24 hours or for no-shows. If weather or waves are unfavorable, trips may be rescheduled or refunded at the captain’s discretion, decided at time of sail. If weather ends a sail in the first hour, you may reschedule or get a refund; after halfway, the charter is considered complete. Changes allowed outside 24 hours.

    Meeting details

    1201A Miracle Strip Pkwy SE, Fort Walton Beach, FL 32548, USA

    Experience provided by Destin Sailing Adventures
    Experience provided by Destin Sailing Adventures

    How can we help?

    We are here to assist with special requests, large groups, last minute needs, and any questions you may have.

    Call or text (650) 414-7338

    Reference #3JQ64D

    Three Hour Adventure

    $426.81

    0

    Four Hour Adventure

    $548.76

    0

    Five Hour Adventure

    $670.71

    0

    Six Hour Adventure

    $792.65

    0

    Nine Hour Adventure

    $938.05

    0

    Why book through Greetwell?

    • No Added Fees

      No booking or service fees, ever

    • Concierge Support Included

      Real humans ready to help with timing, questions, or special requests

    • Free Cancellation Available

      Most experiences can be cancelled for a full refund

    Discover what we've curated for you

    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

    Great for groups

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