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.

Key West Sailing Charter location

Our Key West Sailing Charter Fleet

Sailing Cats

Southern Cross Catamaran

Southern Cross

Leopard 48

4 Cabins | 4 Heads | 48 ft
dream reach leopard 44

Dream Reach

Leopard 44

4 Cabins | 4 Heads | 44 ft
Honu Kai Catamaran

Honu Kai

Seawind 1260

3 Cabins | 2 Heads | 41 ft

Imi Ola

Seawind 1260

3 Cabins | 2 Heads | 41 ft

Stay Glassy

Nautitech 40 Open

4 Cabins | 2 Heads | 40 ft
Santiago Exterior

Santiago

Fountaine Pajot, Lucia 40

3 Cabins | 3 Heads | 40 ft
Go Slow Catamaran

Go Slow

Seawind 1160 Lite

3 Cabins | 2 Heads | 38 ft

Power Cats

Mia Exterior

Mia

90 Power Yacht

4 Cabins | 5 Heads | 90 ft
Andiamo Exterior

Andiamo

Leopard 51 Powercat

4 Cabins | 4 Heads | 51 ft
Ever Summer Exterior

Ever Summer

Fountaine Pajot MY44

3 Cabins | 3 Heads | 44 ft
PDQ 34 Power Catamaran

Traveler

PDQ 34 Power Catamaran

2 Cabins | 1 Heads | 34 ft
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