Key West Sailing Tours

unique sailing experience

Exceptional Schooner Sailing Tours

Sailboat on calm sea at sunset with clear sky and scattered clouds.

Schooner Champagne Sunset Sail—Key West’s Premier Cruise

As the schooner glides into open waters, unfurl the sails and take in views of historic landmarks. Sip on champagne or a signature cocktail while enjoying appetizers as sunset paints the sky.

Starting At

$109.95

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Silhouetted sailboat at sunset with passengers on the water.

Key West Sunset Sailing Aboard the Windjammer

On a wooden schooner, watch the sun dip below the horizon. The two-masted vessel glides past historic sites as you savor hors d’oeuvres and sip champagne or premium beer. Join in hoisting the sails for an authentic sailing experience.

Starting At

$79.95

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Sailboat with people on board sailing on blue water, clear sky.

Windjammer Classic Day Sail – Authentic Schooner Ride

Hoist the sails on a traditional two-masted schooner, joining the crew in an age-old maritime tradition. Navigate past iconic landmarks while enjoying complimentary beverages and spotting dolphins or seabirds along your journey.

Starting At

$49.95

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People kayaking on a clear blue river surrounded by greenery.

Bugeye Backcountry Eco Tour – Key West Eco Adventure

Sail on a wooden schooner to secluded mangrove islands, where shallow waters invite exploration. Paddle through calm channels in sea kayaks, learning about the vibrant ecosystem. Snorkel among sponge gardens, observing tropical fish and marine life. Back aboard, enjoy a fresh buffet lunch with beverages as you return from this eco adventure.

Starting At

$119.95

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