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    Danger Charters

    Danger Charters

    4.9 • 5.8K reviews
    Key West, FL

    Danger Charters creates personalized on-the-water experiences for guests looking to relax, explore, and make the most of their time by the coast. With knowledgeable guidance and a welcoming approach, each private outing is tailore...

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    Book Danger Charters

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    Private Sunset Cruise in Key West

    Cruise Key West harbor at sunset with your group and captain

    $427.17
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    Key West Sunset Sandbar & Snorkel Sail

    Relax on a schooner with snorkeling, sandbar time, snacks, and drinks

    From$147person
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    Private Key West Sunset Sailing Charter

    Private 2-hour sunset sail for up to 30, with wine, beer, and hors d'oeuvres included

    $3,499.79
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    Sail, Snorkel & Kayak Key West Sunset Cruise

    Sail a historic schooner, snorkel and kayak, then cruise into the Key West sunset

    From$147person
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    Private 1.5-Hour Schooner Sailing Charter in Key West

    Charter a private historic schooner sail with drinks and snacks included

    $1,712.96
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    4.5-Hour Sail, Snorkel & Kayak Tour in Key West

    Sail, snorkel, and kayak on a historic schooner with drinks and snacks included

    From$134person
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    Sail a Key West Wine Tasting Sunset Cruise

    Sail a historic schooner at sunset with wine, beer, and small bites

    $147.66person
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    Sail, Snorkel & Kayak Charter in Key West

    Private Key West schooner charter with snorkeling, kayaking, drinks, and snacks

    $2,408.85
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    Key West Private Boat Charter with Snorkeling

    Customize your Key West day on a private boat with snorkeling gear and sandbar stops included

    $694.82
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    Key West Sunset Sail with Wine & Craft Beer

    Sip fine wines and craft beers on an intimate schooner sail as the sun sets off Key West’s coastline

    $147.82person
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    Key West Day Sail with Snorkel & Kayak Lunch

    Sail Key West's clear waters, kayak mangrove islands, snorkel vibrant reefs, and refuel with a buffet lunch—all in one day.

    From$186person

    Review summary

    4.9
    Excellent
    5.9K reviews•Google Maps
    5,548
    135
    27
    15
    21

    Key West sailing doesn't get much better than this, according to travelers who consistently rave about their time on the water here. Whether you're booking the adventure combo with snorkeling and kayaking through the mangroves or opting for the more leisurely sunset wine cruise, you're apparently in for something special. The crew members get called out by name again and again, with captains like Mary, Janet, Anthony, and Micah earning particular praise for being knowledgeable, professional, and genuinely fun to be around. People love that these aren't massive cattle-call operations. Groups tend to max out around 16 passengers, which creates an intimate vibe where the crew can actually give you personal attention and fellow travelers become part of the experience rather than just anonymous faces. The full-day excursions seem to be the showstoppers. You're looking at snorkeling (though not on a reef, so temper expectations accordingly), kayaking around mangrove islands with solid ecology commentary, plus snacks and unlimited drinks throughout. One couple said it was the best day of a rough year, which speaks volumes. The sunset sails hit differently too, with proper wine flights paired with cheese and appetizers, all enjoyed under actual sail power. A few practical notes: the snacks are described as good but light, so consider bringing extra food if you're prone to getting hungry. Weather can look sketchy before departure but often clears up, and you might even spot manatees at the dock. Multiple repeat customers say this is their go-to charter year after year, which tells you everything about consistency.

    What people are saying

    Review 1 of 4
    5/5

    We recently were on Vacation in Key West where we scheduled the Key West Wind and Wine sailing. The crew was amazing, the wine was amazing as were the Hors d'oeuvres. Do not worry if you do not like wine there are other options like soft drinks or beer. One thing I really loved about this sailboat with Danger - it was far more intimate than the larger options with MANY people. We went at the end of August and it was hot and the breeze lower than normal and we still had an amazing time. One of my favorite nights out that week and you can’t beat the views on the water! And that day we actually saw a few water spouts!

    Photo of Tricia Craft

    Tricia Craft

    August 31, 2026

    Review 1 of 1
    5/5

    We recently were on Vacation in Key West where we scheduled the Key West Wind and Wine sailing. The crew was amazing, the wine was amazing as were the Hors d'oeuvres. Do not worry if you do not like wine there are other options like soft drinks or beer. One thing I really loved about this sailboat with Danger - it was far more intimate than the larger options with MANY people. We went at the end of August and it was hot and the breeze lower than normal and we still had an amazing time. One of my favorite nights out that week and you can’t beat the views on the water! And that day we actually saw a few water spouts!

    Photo of Tricia Craft

    Tricia Craft

    August 31, 2026