We have four boats that we’d love to take you sailing on! From Key West’s first charter sailboat, High Tide, to one of the oldest, most-historic boats located in the Florida Keys, Schooner When and If, we have the resources to pull off any kind of trip!

All of our boats are the real deal. We aren’t out there to just motor around. As soon as we pull out of the harbor, sails go up and the engine goes off. Join us for an authentic sailing experience!

High Tide

Conch West

When and If

Free Spirit

High Tide is the do-it-all boat of single-day charters. She was built specifically for cruising the backcounty, and being a comfortable-yet-gorgeous ride. In the right conditions, she’ll out-sail even the fastest of the other boats in the harbor. For any day trip you can think of, this is the perfect boat.

Conch West is a ketch, perfect for sailing excursions to snorkel the colorful coral and marine life of the Great Florida Reef—the only living barrier reef in the United States, and the third largest coral reef in the world!

Schooner When and If was General Patton’s personal sailboat and has a history as incredible as her looks. She’s a wooden 1939 John Alden schooner, built with luxury and class but with a sailing experience unmatched by modern boats. She may be the premium sunset cruise or day sail yacht, but she also has a racing physique that competes with boats 70 years her junior.

Free Spirit is great for overnights and makes for a wonderful, once-in-a-lifetime family experience, learning to sail and spending the night at one of the amazing hideaways Key West’s water has to offer.

Can’t decide on a boat? Choose which trip you want instead.