Key West Sailing Charters

Experience the beauty and wonder of an unspoiled tropical paradise without ever leaving the Continental United States. Our Key West sailing charter destination is located minutes from all the downtown Key West attractions and Duval Street night life, yet a short sail away from pristine reefs, underwater nature preserves, and uninhabited island locations such as the stunning and secluded Marquesas. Kayak, paddle board, and snorkeling excursions will open to you the offshore beauty offered only in the Florida Keys. Our native Floridian staff knows how to find the best activities on land or at sea, to guide you as you plan a unique and customized getaway.

Our Key West Sailing Charter Fleet

Sailing Cats

Southern Cross Catamaran

Southern Cross

Leopard 48

4 Cabins | 4 Heads | 48 ft
Indoses boat


Fountain Pajot Elba 45

3 Cabins | 3 Heads | 45 ft
dream reach leopard 44

Dream Reach

Leopard 44

4 Cabins | 4 Heads | 44 ft

Sugar Magnolia

Lagoon 42

4 Cabins | 3.5 Heads | 42 ft
Honu Kai Catamaran


Seawind 1260

3 Cabins | 2 Heads | 41 ft
Honu Kai Catamaran

Second Sight

Seawind 1260

3 Cabins | 2 Heads | 41 ft

Stay Glassy

Nautitech 40 Open

4 Cabins | 2 Heads | 40 ft

Power Cats

Ever Summer Exterior

Ever Summer

Fountaine Pajot MY44

3 Cabins | 3 Heads | 44 ft

Key West Attractions

Duval St. in Key West

Historic Duval Street

One of the most popular destinations on the island of Key West is Duval Street. Visit the Ernest Hemingway Home and Museum where you can take in some history about the writer and meet a legendary six toed cat. If you feel like taking in some nature, visit the Key West Butterfly and Nature Conservatory where there are 50 - 60 different species of live butterflies from around the world. On Duval Street, you can simply take a stroll and hear live music, see art galleries, enjoy coffee shops and great restaurants, or find unique souvenirs at one of the many boutiques.

Romantic Sunsets

Beautiful sunsets are what Key West is all about. Enjoy the soothing ocean breeze, a glass of wine, and relax to the backdrop of the setting sun on your own private catamaran cruise. Watching the sunset has become an integral part of everyday life in paradise. This is one tradition you don’t want to miss!

Key West sunset
snorkeling in Key West

Crystal Clear Snorkeling

Key West offers many beaches and reefs where you can experience snorkeling in warm crystal-clear water. At Cottrell Key, see the unique sponge garden and large coral reefs. It is also an excellent place to see dolphins, sharks, stingrays, and Goliath groupers. Fort Zachary Taylor is considered one of the best offshore snorkeling spots in Key West where there are a variety of tropical fish species and living coral to see. A favorite among snorkeling enthusiasts is Sand Key Lighthouse Reef. With a remote location and strict no-take policy, the Sand Key Lighthouse Reef is one of the healthiest coral gardens in Florida.

Pristine Sandy Beaches

Craving a drink in your hand and your toes in the sand? Check out the turquoise waters at Smathers Beach. Rental shops are available with beach chairs, shade umbrellas, kayaks, jet skis and much more. Try South Beach for calm, shallow waters that are excellent for swimming and great for families. Higgs Beach is unique for its historical significance. Take a wander around, and you'll find monuments dedicated to the 19th-century slave cemetery located on the site. There is also a pier at Higgs Beach, where visitors can often spot stingrays and other marine species.

Key West south beach
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