Free Sail Away Trips on our Classic Sailing Vessels

Sunset Sail Key West 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.

We want to share our love of sailing with you. Have a real sailing experience.

Come sail away with us for 75 minutes on one of our classic sailing vessels:

• High Tide 1978 33' Glander Sloop, Key West's first private charter boat
  
  


• Free Spirit 1977 33' Lazy Jack Schooner (Key West's Smallest Schooner) Designed by Ted Brewer, she is one of only 25 ever built
  
  


• Conch West 1973 42' Island Trader She has been around the world twice.

Saturday, November 26th 2016 @ 10am - 11:15am RESERVE HERE

Saturday, November 26th 2016 @ 12pm - 1:15pm RESERVE HERE

Saturday, November 26th 2016 @ 4:30pm - 6:30pm RESERVE HERE

Private Sunset Charter for up to 6 guests $175 plus tax: Saturday, November 26th 2016 @ 4:30pm - 6:30pm RESERVE HERE

You must be at the dock 15 minutes prior to departure or your seat will be given away. Please bring your own beverages. Every passenger, no matter the age, must have a ticket. It is customary to tip the crew.

Treasurer: Win a Free Private Day Sail on Free Spirit. All passengers will be entered in a drawing. Please see them for full details, rules and regulations. Value $295

If you can't make one of these sails, please check out all our other events happening during I Love Stock Island including