sskw-logo-horizontal

Guess Who's Back?!

The perfect Holiday gift!

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

Lilypaddling!

Time to cool off on the Lilypad!

Now's your moment...

The sun setting, the sound of the sea as you and your beloved sail into the sunset…Now’s your moment!

Swim With The Fishes

Check out the unique ecosystem that supports a profusion of life surrounding the Florida Keys