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

New to the Fleet: Schooner Metani!

A modern classic built to the gorgeous lines of a John Alden design, Metani is a delight combining an exotic hardwood hull and a soaring modern schooner rig for the ultimate in sailing comfort and performance. Her ample deck space and comfortable cockpit accommodate up to six guests for private charter out of Stock Island Marina Village.
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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!

Check Out Our New Ship's Store!

Get your gorgeous 2021 When And If calendars here! 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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When And If is back DOWNTOWN for Winter 2020-21!

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 50% off private charters this season only, this is a historic sailing experience not to be missed.
Sail When And If

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