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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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.
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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
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's Great Lakes Tour

When And If will be touring the Great Lakes this Summer as part of Tall Ships 2025. From Brockville, ON to Duluth, MN with numerous ports in between, come visit When And If for sailaways and happy days!
Click to see her schedule and book your ticket!
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...
News

Wreckers' Race Season

Starting the third Sunday in January and every month through April, 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!
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.
Shop Now
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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