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JOIN US ON A TRUE, CLASSIC SAILING EXPERIENCE

Offering exclusive private sailing charters at an affordable price, Sunset Sail Key West is a small, locally-owned fleet of sailboats and sailors in beautiful Key West, Florida.

We love sailing, and that’s what we’re here to do! Join us on one of our boats and experience the Florida Keys from the best place you can—out on the water! We depart daily from Key West and Stock Island on our authentic sailing vessels.

It’s not just about sunset sails, either! Come sailing with us to snorkel the backcountry, have your wedding or private party, or see anything from the sunrise to the full moon.

Call Us
(305) 587 4488

When And If is back!

Welcome back, When And If!

The schooner When and If is back home with Sunset Sail Key West for Winter 2017/18!

Join us on 12/10

The annual ILSI festival is back in town – join us for special-rate daysails and Sunset Sails aboard When and If!