Welcome to Sunset Sail Key West

Welcome to Sunset Sail Key West

Sunset Sail Key West

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Welcome to Sunset Sail Key West, Key West’s most versatile custom charter experience. With four beautiful vintage boats, great local captains and crew, and the pristine waters of the Florida Keys at our disposal, we’re confident that we’ll have everything you need to make your dream sail come true.

Four Vintage Boats

high tide w schooner

Our four classic boats are ready to take you sailing any time of day or night. With private charter as well as ticketed sails available and a crew to take you away with the wind, we’re your choice for an exclusive, custom sailing trip in Key West. Get to know our fleet here.

Perfect Sailing

2 girls

No matter what kind of sailing experience you’re looking for, we’ve got you covered. Choose from our a-la-carte menu for a sun-soaked daysail, a romantic sunset, or a swim call adventure. Enjoy the privacy and flexibility of booking a private charter, or join a ticketed sail to share the sunset.

Our most popular trips

Private Sunset Sail

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Groups of up to 12 on your own private boat

Historic Sunset Sail

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A shared experience on a beautiful vintage yacht

Key West Daysail


Get some sun and catch the cool sea breeze

Trips on Schooner When And If

Private Sailing

Something Extra Special

See all our Key West Sailing Trips Here