Schooner Jolly II Rover Sunset Sail - Key West FL

Step aboard the Schooner Jolly II Rover for one of Key West’s most recognizable sunset sailing experiences. Departing from the Historic Seaport, this classic tall ship is known for its distinctive red sails, square-rigged topsail design, and hands-on sailing atmosphere.

The 2-hour “Red Sails in the Sunset” cruise gives guests a true wind-powered Key West experience instead of a loud party boat ride. Passengers can help raise the sails, take a turn at the wheel, and enjoy the signature cannon-fire tradition as the schooner passes Mallory Square, Sunset Key, Fort Zachary Taylor, the Truman Annex, and the open Gulf horizon.

The Jolly II Rover is a BYOB-friendly sunset sail, with bottled water, ice, cups, and bottle openers provided. Guests may bring their own drinks, snacks, or small picnic-style cooler, making this a flexible and affordable choice for couples, families, photographers, and visitors who want an authentic tall ship experience.

For specific dates, departure times, and current sail availability, please use the Check Availability button.