Sunset Sail Key West, Boat Sailing Charters In Florida
  • 202 Williams Street Key West Florida 33040
  • 365 Days a Year
  • 3055874488

Authentic private boat sailing in the Keys
Offering exclusive small-boat sailing charters at an affordable price, Sunset Sail Key West is a locally-owned fleet of sailboats run by experienced, fun sailors in beautiful Key West, Florida.
Our boats are carefully selected to be intimate, historic and characterful – each one has her own story. Our captains are passionate sailors who know the keys and love to share their knowledge of the local history and wildlife. Our guests are people who want to have some fun, do something a bit more off the beaten path, and take a break from the crowds to enjoy a genuine

Key West sailing Experience
There’s tons of things to do on the water, and it’s not just about sunset sailing! Come sailing with us to snorkel the barrier reef or the backcountry, take a daysail off the island, have your wedding or private party, toast the sunrise or sail under the full moon. 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!
Our lovely flagship, 33ft sloop High Tide departs daily from downtown Key West, and our 50ft ketch Conch West and 32ft schooner Free Spirit run every day out of Stock Island for some great blue-water sailing and reef snorkelling. We’ll shut off the engine to allow you to enjoy the peace and beauty of the keys all around while you help raise sail, take a turn at the helm…or sit back and relax!

Special Guest Ship When and If…
We are proud to announce we have a special guest ship at Sunset Sail Key West for this winter only – the stunning historic schooner yacht When and If, built in 1939 for General George Patton. She’s also available for day sails, sunset sails and private charters – but she’s only here ’till June so don’t miss out!

What could be more romantic than a beautiful sailboat, your closest friends, a sunny afternoon and a gorgeous sunset – the perfect way to say “I do!” With space on our prettiest flagship vessel High Tide for up to 10 guests she is the perfect way to enjoy an intimate, fun and unusual wedding with your loved ones. For larger parties our guest ship, the historic schooner When and If can take up to 32 guests and is here ’till June – don’t miss out!
If you’d like flowers, lights, balloons, live music, hors d’oeuvres, champagne, cake or anything else you have only to let us know and we’ll do everything we can to make your special day completely perfect!

Custom Charters
At Sunset Sail Key West we pride ourselves on flexibility and delivery of custom requests. Perhaps you’d like to take the boat out for the whole day and go for a cookout on a deserted island? Perhaps you’re low on time and can just squeeze in an hour? Perhaps you’d like to sail out for a while, pick up a friend at the dock and then continue your afternoon on the water? Perhaps you’d like the cockpit filled with roses when you propose to your partner? We’re pretty sure we can make it happen, so don’t be shy – tell us about your dream sail and we’ll make it happen!