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Key West Sailing

Sailing and Key West have a history that dates back over 400 years—yet Sailing remains as real and wonderful a part of Key West today as ever! Captains and mates hauling sails. Soft tropical breezes. Sunset vistas of unspoiled horizons. Drawing upon a rich history of maritime tradition and world-famous seamanship, Key West Sailing is a vacation must.

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Wind & Wine Key West Sunset Sail

The Wind & Wine Key West Sunset Sail has been honored with a #1 rating on Trip Advisor three years running. See the sunset on a beautiful 65ft sailing boat.

Times: 5:00PM Duration: 2 hours (approx.) Activity Level: Easy
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Sail, Snorkel, Kayak with Sunset Option

Enjoy an unforgettable morning or afternoon of sailing, kayaking and snorkeling in the pristine marine wilderness of the Key West National Wildlife Refuge.

Times: 9:30AM, 3:30PM Duration: 4.5 hours (approx.) Activity Level: Moderate
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Backcountry Safari Key West

Spend an unforgettable day sailing emerald waters, kayaking mangrove-shaded channels and snorkeling coral gardens in an unspoiled marine wilderness.

Times: 10:00AM Duration: 6.5 hours (approx.) Activity Level: Moderate
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