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

Commander Hawk Excursions

"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.

Day Sails and Sunset Sails

Reef Snorkel Trips

Book With Commander Hawk Excursions

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.

Private Charters

Stand-Up Paddle Boarding, Kayaking, Sailing

Out Island Overnight Escape

Dry Tortugas Trips

Book With Tortuga Sailing Adventures

Sunset Sail Key West

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.

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

Learn to sail with one of the best in the business! Harmony Sailing Academy offers ASA sailing courses designed to bring you confidence and experience.

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