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

Guess who's back?!

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

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!

2018 Wreckers Race

Every boat in Key West races 7 miles from the bight to the reef in remembrance of the wreckers of old…