Private & Shared Sailing Charters

Sunset Sail
Key West

Set Sail in the Key West Sun. Reserve your intimate and elegant a la carte private charter or legendary historic schooner sunset sail. Passion drives our success, let us share our view of Key West with you!

Real. Classic. Sailing.

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Get inspired with our most popular trips!

Schooner Sunset Sail

A two-hour sunset sail on one of our stunningly beautiful and historic schooner yachts.
Intimate. Historic. Unparalleled.
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Private Sunset Sail

Set sail on Key West's premier sunset sailing sloop. USCG certified
Comfortable. Elegant. Local Charm.
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Chillout Lilypad Sail

Sail away on your private charter into Key West's wildlife preserve
Your charter. Your way!
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Key West Daysail

Sun, sea and Keys breeze. 90 min. Key West Harbor Daysail
Personable. Private.
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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 classic sailboats, each with their own unique charm and appeal. A custom sloop and two historic schooners 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
News

The Schooners Are Coming!

Back in Key West for their WInter Season from October through June, our stunning 1930s wooden schooner yachts When And If & Malabar X are ready to take you sailing in style all day every day!
Book your classic schooner cruise here
News

Book your Holiday Party with Sunset Sail Key West

Show your employees some love and support a truly local family business! Treat your team to a night playing tourist in their home town by doing what Sunset Sail Key West does best - a classic schooner sunset sail.
Book early to avoid disappointment and celebrate the Holidays in style!
News

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.
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