Private & Shared Sailing Charters

Sunset Sail
Key West

Home to Key West's finest schooner sunset sail. Beautiful sunset sailing from downtown Key West and the luxurious Perry Marina.

Real. Fun. Sailing.

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4.89/5
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Avg. after 1,146+ ratings.

Get inspired with our most popular trips!

Schooner Sunset Sail

A two-hour sunset sail on the gorgeous schooner When and If
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Private Sunset Sail

Groups of up to 12 on your own private yacht
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Chillout Lilypad Sail

Swim call! Jump into that beautiful aqua water
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Key West Daysail

Sun, sea and Keys breeze. Private charters groups up to 6, 12, and 32 guests
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Privates Charters

Discover Your Perfect Private Charter

Set out on a snorkeling, stargazing, or sunset sail, or build your own custom trip. Romance, relax or unwind from the privacy of your own chartered sailboat.

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Shared Trips

Daysails & Sunset Sails

Rise above the crush of the crowds and set sail on a unique sunset sail experience, with a few friends you haven’t met yet. A personable local crew and captain will treat you to a stunning sunset view from the deck of an unforgettable vessel– General Patton’s elegant, private schooner When and If.

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Three Classic Boats

View Our Fleet

We sail a fleet of three vintage sailboats, each with their own unique charm and appeal. A custom sloop, a classic ketch, and a historic schooner are waiting to make memories with you on the crystal clear waters of Key West. Each boat is suited to different types of outings, so take a moment to get acquainted with our vessels.

Our Fleet
About Us

Real. Fun. Sailing.

You could say that we’re obsessed with sailing, but that’s putting it lightly. With unmatched passion and a fleet of classic boats, we offer authentic, fun, unique ocean adventures in Key West.
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A proposal to remember at Sunset Sail Key West

With our selection of coral, pearl and diamond proposal packages we're sure to have everything you need for the perfect moment.
I'm thinking about it...
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Wreckers' Race Season

Starting the third Sunday in January and every month through April, book your seat on When And If to race a winner to the reef for salvage rights as in the days of Old!
Race a Winner!
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Classic Schooner Blue Angels Viewing Cruise

For the best view of the Southernmost Air Spectacular 2025 come admire the pride of America's Air Force as they soar overhead. Glimpse the planes through the rigging as they fly above, or enjoy the panoramic view to the horizon from the deck.
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Check Out Our Ship's Store!

Your one stop shop for all our awesome swag. Take a look at our selection of hats, tee shirts and other commemorative items, and have them delivered right to your door.
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Bringing decades of experience and a bottomless love of sailing, our locally-owned fleet and passionate sailors share the beauty of Key West– from on the water.
Friends of SSKW
Sunset Sail SalemSchooner When and If
Contact
sailing@sunsetsailkeywest.com(305) 587 4488
202 William Street
Key West, Florida 33040
© Copyright Sunset Sail Key West 2020