Schooner When And If, Operated by Sunset Sail Key West. Built in 1939 for General George Patton and designed by legendary naval architect John G. Alden.
Key West's First USCG Certified Sailing Charter Vessel. Built in 1978 by Glander Boats of Islamorada, FL. High Tide is Key West's Most Versatile Charter Boat. Shallow Draft with a Large Cockpit for Up to 12 Guests and 2 Crew
Key West Wreckers Race For an Incredible Opportunity to Re-enact History in the Key West's Waters. Last Sunday of the Months of January, February, March and April
Private & Shared Sailing Charters

Sunset Sail
Key West

Set Sail on a Historic Schooner or a Private Charter on Key West's Premier Sailing Vessel, the Sloop High Tide - Key West's Most Memorable Day and Sunset Cruises Passion drives our success, let us share our view of Key West with you!

Real. Classic. 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 one of our stunningly beautiful and historic schooner yachts.
Intimate. Historic. Unparalleled.
$109pp limited to 28 guests
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Private Sunset Sail

Set sail on Key West's premier sunset sailing sloop. USCG certified
Comfortable. Elegant. Local Charm.
From $645 up to 12 guests
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Chillout Lilypad Sail

Key West Private Charter Sandbar and Dolphin Watch Sandbar Cruise Includes a 6' x 18' Floating Lily Pad for On the Water Fun
Sail away on your private charter into Key West's wildlife preserve
Your charter. Your way!
From $595
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Key West Daysail

Key West's Most Romantic Sunset Option is an Intimate Private Charter Onboard Key West's Premier Sailing Vessel. Fully Restored and Immaculately Maintained. Curate Your Private Charter Today!
Sun, sea and Keys breeze. 90 min. Key West Harbor Daysail
Personable. Private.
From $395
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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
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

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.
I'm thinking about it...
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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