Journey back to the golden age of pirates and privateers aboard Key West’s iconic Jolly II Rover, a square-rigged topsail schooner renowned for its vibrant red sails and authentic tall-ship charm. This 80-foot vessel invites adventurers to explore the glistening waters on a two-hour day sail or the famous “Red Sails in the Sunset” tour, gliding past lively Mallory Square. Passengers can raise the sails, fire cannons, and even take the helm for a hands-on experience that echoes the region’s spirited past. For a more personalized voyage, private charters cater to special occasions—from sunset weddings to all-day excursions anchored in remote waters like Boca Grand. Proudly owned by Bill Malone since 2003, the Jolly II Rover has weathered storms and found a permanent home at Key West’s Historic Seaport, continuing its legacy of adventurous, old-world sailing. Celebrated by outlets such as USA Today and National Geographic for its legendary sunset cruises and striking presence, this topsail schooner offers an unforgettable taste of maritime history in the heart of the Florida Keys.
