Private & Shared Sailing Charters

Sunset Sail
Key West

Have the sea to yourself with Sunset Sail Key West—chartered sailing trips led by us, tailored to you.

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Get inspired with our most popular trips!

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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Sunset Sail on When & If

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

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.
Sail When And If

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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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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