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
TripAdvisor
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

Come Together on a Shared Charter

Rise above the crush of the crowds and set sail on a unique shared sunset charter, 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.
News

When And If is back at beautiful Stock Island Marina!

The gorgeous 1939 wooden schooner built for General George S Patton to sail around the world "When the war is over, and If I live through it." With sailing available every day and private charters starting at just $995, this is a historic sailing experience not to be missed.
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News

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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News

Wreckers' Race Season Is Back!

Starting the third Sunday in January, 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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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