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    1. Local experiences
    2. /Things to do in Key West…
    3. /Water Activities
    4. /Sailing
    5. /Men's Sailing Cruise in Key West
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    Men's Sailing Cruise in Key West

    A clothing-optional all-male sailing trip with snorkeling, sandbar, or kayaking

    4.9 stars• 414 reviews

    Duration

    4 hrs

    Ideal For

    Up to 30 people

    Includes

    Snacks, water, snorkel gear

    Highlights

    Join an all-male, clothing-optional sailing outing on Key West waters. Sandbar and snorkeling are typical when weather and tides allow, with kayaking available on some days.

    • Sail aboard a flat, comfortable catamaran
    • Snorkel, swim, or kayak as conditions allow
    • Relax in the water or in the boat's shade
    • Bring your own drinks to keep chilled in onboard coolers
    • Enjoy a clothing-optional atmosphere with other gay men

    What's Included

    • Snorkeling equipment
    • Kayak gear
    • Flotation gear
    • Snorkeling instruction
    • Bottled water
    • Fresh organic snacks
    • Wetsuits during winter months

    Important details

    • Ages 18+ only
    • Arrive 15 minutes before departure for check-in
    • Bring a towel and reef-safe sunscreen
    • Do not bring spray sunscreen
    • Expect activities to change with weather and tide conditions
    • Expect the trip to run in light rain and moderate weather; severe or unsafe weather may cancel the activity
    • Groups of 6 or more have an automatic 20% gratuity added after reservation; it is not included in the listed price

    Cancellation Policy

    Free cancellation up to 6 days (144 hours) before departure. No cancellations or rescheduling within 6 days. Private charters can be refunded until 30 days before boarding; no refunds or rescheduling within 30 days.

    Product ID: X6ED7B

    FAQs

    Bring a towel, reef-safe sunscreen, a swimsuit, and any additional snacks or drinks you want. Do not bring spray sunscreen. Bring layered clothing between November and March.

    Clothing is optional. Wear as much or as little as you like.

    Expect the captain to choose activities based on conditions. Sandbar visits and snorkeling are typical when conditions allow; kayaking may be offered instead.

    Meeting details

    Blu Q Catamaran, 120 Margaret Street, Key West, FL 33040

    Experience provided by Blu Q Catamaran

    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

    Adult

    $146.42

    Ages 18+

    0

    Private Charter

    $4,297.11

    Up to 30

    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

    4.9
    Excellent
    414 reviews•Google Maps
    370
    3
    6
    2
    6

    Smalls, Hadden, and the rest of the crew have built a serious reputation for making people feel welcome on the water. The vibe is relaxed and judgment-free, with most trips centered around snorkeling at the coral reef, walking a sandbar ten miles offshore, or simply soaking up the sun on the catamaran. Wildlife sightings, including sharks, dolphins, and turtles, come up often enough to feel like a genuine bonus rather than a lucky fluke. The all-male day sail draws a loyal crowd, with plenty of repeat visitors and couples celebrating special trips. Guests consistently praise the crew's energy and attentiveness, and the food and drink offerings get strong marks too. If you're on the fence, the reviews here make a pretty clear case to just go ahead and book it.

    What people are saying

    Review 1 of 5
    5/5

    First time sailing with Captain Smalls and First mate Haddon Labor day weekend. They work well as a team and enhance the experience! All around wonderful time from beginning to end. Fun on the water with nice group of men and shedding the clothes is icing on the cake!. Thanks guys!

    Photo of Michael Spatz

    Michael Spatz

    September 9, 2026

    Review 1 of 1
    5/5

    First time sailing with Captain Smalls and First mate Haddon Labor day weekend. They work well as a team and enhance the experience! All around wonderful time from beginning to end. Fun on the water with nice group of men and shedding the clothes is icing on the cake!. Thanks guys!

    Photo of Michael Spatz

    Michael Spatz

    September 9, 2026

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