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    1. Local experiences
    2. /Things to do in Fort Walton Beach…
    3. /Water Activities
    4. /Sailing
    5. /Proposal & Anniversary Sailing Cruise in Fort Walton Beach
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    Proposal & Anniversary Sailing Cruise in Fort Walton Beach

    Sail with a licensed captain for a proposal or anniversary cruise

    4.5 stars• 28 reviews
    From$492incl. taxes and fees

    Duration

    2 Hour, 3 Hour

    Ideal For

    Up to 6 people

    Includes

    Licensed captain, snorkel gear

    Highlights

    Plan a proposal or anniversary cruise aboard an insured Stiletto 27 Special Edition with a licensed local captain. Bring your own food and drinks, relax under the sunshade, and enjoy time on the water.

    • Choose a 2- or 3-hour private sail for up to 6 passengers
    • Celebrate a proposal or anniversary cruise with captain support
    • Relax on bean bag chairs with a sound system onboard
    • Bring your own beverages and food for the trip
    • Plan ahead for gratuity, which is not included

    What's Included

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

    Things to know

    A photo package and Insta360 and GoPro are available at checkout.

    Cancellation Policy

    Cancel 24+ hours before arrival time for a full refund. No refund within 24 hours or for no-shows. If weather or waves are unfavorable, the trip may be rescheduled or you will receive a full refund; weather calls are at the captain’s discretion at the time of sail.

    FAQs

    Arrive about 15 minutes early for parking and waivers. Check in behind the Tackle and Bait Shop, then park in the upper parking lot in front of the Adventure Marina Sales and Service building.

    Bring flat shoes, beverages and food, polarized sunglasses, a hat, a lightweight shirt, towels, a camera, and cash for gratuities. Apply sunscreen before you get on the boat, in a cool place.

    No. Gratuity is not included, so plan for an extra tip.

    Meeting details

    1201 B Miracle Strip Pkwy Fort Walton Beach, FL US 32548

    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 1-877-GREET-WELL

    Report an issue

    Reference #JBWNPJ

    Three Hour Adventure

    $492.90

    0

    Why book through Greetwell?

    • No Added Fees

      No booking or service fees, ever

    • Concierge Support Included

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    • Free Cancellation Available

      Most experiences can be cancelled for a full refund

    Discover what we've curated for you

    Review summary

    4.5
    Excellent
    28 reviews•Google Maps
    22
    1
    1
    1
    2

    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 2
    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

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