Let our sweet island breeze fill your sails.

From majestic schooners to racing regattas, there is no better way to connect with Key West than by letting its wind in your sails. With its clear blue water, sweet island breeze and countless sights to see, Key West is the ideal sailing destination.

Sailing solo? We recommend sailing to a historic lighthouse like Sand Key Light or American Shoal for a glimpse of Key West’s past.

Interested in chartering a local guide? Seek out Tortuga Sailing Adventures for private sailing excursions and experience Key West’s quintessential tropical waters from the convenience of the Stock Island Marina docks. Stock Island is also home to historic vessel, When & If, the custom sailboat and dream of General George S. Patton. When & If is also available for open sails and private charter.

On-Site Experience Partners

Sail With Courage

"Sail with Courage" during this private excursion for you and up to 5 friends, and you might just catch a glimpse of the elusive green flash during a famous Key West sunset.

Capt. Tim will show you and your group a great time under wind power, while all your stresses will melt away with the sunset!

Day Sails and Sunset Sails

Reef Snorkel Trips

Book With Sail With Courage

Tortuga Sailing Adventures

If you're looking for the ultimate Florida Keys sailing, snorkeling and island hopping experience, Tortuga Sailing Adventures has the answer. Their focus is always on you during any of your all-private, all-inclusive yacht excursions.

Let their crew do the work while you soak up the sun, take photos to prove the sights to your friends back home, and experience the Dry Tortugas in an exclusive setting private to you and your group!

Private Charters

Stand-Up Paddle Boarding, Kayaking, Sailing

Out Island Overnight Escape

Dry Tortugas Trips

Book With Tortuga Sailing Adventures

Sunset Sail Key West

Kick back and relax, and enjoy a day out on the water. 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.

Be sure to check out their newest experience, the Chillout Sandbar Sail!

Sunrise and Sunset Sails

Stargazer and Full Moon Sailing Trips

Snorkeling Sail Combo Trips

Custom Charters Available

Book With Sunset Sail Key West

Harmony Sailing Academy

Experience the magic of sailing with Harmony Sailing Academy. Raise the sails, crank the winches, and steer a course. Learn from their knowledgeable, friendly instructors who create a fun and relaxed environment, utilizing hands-on education.

Their small class sizes allow you to meet new people and interact with others from around the world. Sailing is not only an adventurous activity, it is also a social activity that promotes teamwork and collaboration, so bring your best jokes and be ready for a good time.

Their three hour sailing lessons are a great way to have a fun and inspiring experience, learn new skills, and join in on an adventure you won't forget. Whether you just want to relax and get a taste of the Keys, or learn as much as possible about sailing, we will get you out there and show you the time of your life!

Multi-Day Courses in Cuba and Key West

ASA 101, ASA 103, ASA 104 Courses

Book With Harmony Sailing Academy

Photo Credit: Tortuga Sailing Adventures


Photo Credit: Tortuga Sailing Adventures


Photo Credit: Tortuga Sailing Adventures