Beat The Crowds With Sunset Sail Key West

Private sailing for up to 12 people on your own private boat

Sunset Sail Key West

Welcome to Sunset Sail Key West, Key West's most versatile custom charter experience. With three beautiful vintage boats, great local captains and crew, and the pristine waters of the Florida Keys at our disposal, we're confident that we'll have everything you need to make your dream sail come true.

Three Vintage Boats

Our three classic boats are ready to take you sailing any time of day or night. With a great selection of private charters and a crew to take you away with the wind, we're your choice for an exclusive, custom sailing trip in Key West. Get to know our fleet here.

Perfect Sailing

No matter what kind of sailing experience you're looking for, we've got you covered. Choose from our a-la-carte menu for a sun-soaked daysail, a romantic sunset, or a swim call adventure. Enjoy the privacy and flexibility of booking a private charter with Sunset Sail Key West. 

Swim Call!

20% off all trips!

Use code BETTER2020 at checkout

Get inspired with our most popular trips!

Private Charter Sunset Sail

Groups of up to 12 on your own private yacht

Chillout Lilypad Sail

Swimcall! Jump into that aqua water

Key West Daysail

Sun, Sea and Summer Breezes for up to 12 people

Sunsets...It's kind of our thing...

Private Sailing All Day Long!

Something Extra Special

When And If - Our Winter Guest