About Schooner Jolly Rover
The Schooner Jolly II Rover is one of Key West's most photographed vessels, an 80-foot Caribbean coastal tall ship with distinctive red sails that has become a landmark of the Historic Seaport. Docked at Greene Street next to the Conch Republic Seafood restaurant, the Jolly Rover offers classic sailing adventures that capture the pirate-era spirit of the Florida Keys.
They run daily day sails and sunset cruises, with each trip lasting roughly two hours. Beer, wine, and soft drinks are included, and the relaxed atmosphere encourages passengers to help hoist the sails or simply lounge on deck and enjoy the views. The captain narrates Key West history and points out marine wildlife along the way, making it educational as well as scenic.
The Jolly Rover stands out for its authentic tall-ship character — this is a real working schooner, not a motorised catamaran dressed up for tourists. Featured in magazines, travel blogs, and TV shows, the vessel has earned a reputation as one of the most iconic sailing experiences in Key West. It's a favourite for couples, families, and anyone looking for a genuine Keys sailing adventure.
