Key West Sailing Adventure

201 William Street Historic Seaport; E-Dock; Slips: E-10, E-11, E-12, Key West, FL 33041

(305) 304-4911


Key West Sailing Adventure offers a variety of private sailing charters that can accommodate up to six passengers. They provide an immersive experience in the waters around Key West, allowing visitors to explore the American Caribbean aboard a sailboat. Their fleet includes the 44’ Morgan sailboat “Wildthing,” known for its smooth ride and sailing ability, the 42’ “St. Vitus Dance,” which has a history with the TV show Miami Vice, and the 37’ O’Day sailboat “Obsession,” which has sailed extensively in the Bahamas and Mexico.

Their sailing packages range from half-day sails to full-day adventures, including lunch and activities like snorkeling, fishing, and learning basic sailing techniques. The full-day sail, for instance, spans 7-8 hours and includes lunch, sanitized snorkel gear, towels, and the guidance of a captain and first mate.

For those interested in a more extended experience, Key West Sailing Adventure offers the Key West Sampler, a unique blend of dockside living and water-based activities. This package allows guests to stay on the boat dockside, explore Key West’s nightlife, and then set sail for a day-long adventure. The package includes sailing, snorkeling, beach-combing, and various other activities.

Their excursions also offer the opportunity for island hopping and destination sailing vacations. These trips can be customized according to the guests' wishes, with options for snorkeling, fishing, beach exploration, and more. Their sailboats are equipped for both local island hopping and long-distance travel, such as trips to the Bahamas.

For special occasions, Key West Sailing Adventure provides packages for weddings and honeymoons, combining a sailing vacation with the celebration of the event.

All their charters and excursions can be tailored to the guests' preferences, making each trip a unique and personalized experience​​​​​​.