



by Schooner Jolly II Rover
How do you want to book?
✓Confirmation before Wed, 9 Sept - card's only charged if it's a yes. If it's a no, still time to book on Viator.
Book on Viator Confirmed right away, but you pay full price.$190This two-hour sailing cruise takes place aboard the Jolly II Rover, a traditional topsail schooner with squared rigging and red sails, docked in Key West's Historic Seaport. You can help raise the sails, steer the ship, or fire the ship's cannons during the cruise. There is no loud music or live band, allowing you to enjoy the sailing experience fully. The route includes sailing past key landmarks such as Man O War Harbor, Christmas Tree Island, the mansions on Sunset Key, Mallory Square, the Navy Mole, and Fort Zachary Taylor. The boat then heads out into the Atlantic Ocean to watch the sunset. The cruise includes bottled water, cups, ice coolers, and snacks. Alcoholic and carbonated drinks are not provided. There is plenty of space to move around and interact with other guests. The operator tries to accommodate wheelchair users, although there is no wheelchair ramp on board.
Historic Seaport and Atlantic Sunset Sail
The cruise lasts two hours, sailing past Key West's Historic Seaport, entering Man O War Harbor, passing Christmas Tree Island, the mansions on Sunset Key, and Mallory Square from the water. It continues by the Navy Mole and Fort Zachary Taylor, then cruises past the State Park and into the open Atlantic Ocean to watch the day's sunset.
120 min
15 minutes before sailing time - In the Historic Seaport at the corner of Elizabeth and Greene streets. At the ticket booth on the dock along side the Conch Republic Seafood Company Restaurant.
End point
15 minutes before sailing time - In the Historic Seaport at the corner of Elizabeth and Greene streets. At the ticket booth on the dock along side the Conch Republic Seafood Company Restaurant.




by Schooner Jolly II Rover
How do you want to book?
✓Confirmation before Wed, 9 Sept - card's only charged if it's a yes. If it's a no, still time to book on Viator.
Book on Viator Confirmed right away, but you pay full price.$190This two-hour sailing cruise takes place aboard the Jolly II Rover, a traditional topsail schooner with squared rigging and red sails, docked in Key West's Historic Seaport. You can help raise the sails, steer the ship, or fire the ship's cannons during the cruise. There is no loud music or live band, allowing you to enjoy the sailing experience fully. The route includes sailing past key landmarks such as Man O War Harbor, Christmas Tree Island, the mansions on Sunset Key, Mallory Square, the Navy Mole, and Fort Zachary Taylor. The boat then heads out into the Atlantic Ocean to watch the sunset. The cruise includes bottled water, cups, ice coolers, and snacks. Alcoholic and carbonated drinks are not provided. There is plenty of space to move around and interact with other guests. The operator tries to accommodate wheelchair users, although there is no wheelchair ramp on board.
Historic Seaport and Atlantic Sunset Sail
The cruise lasts two hours, sailing past Key West's Historic Seaport, entering Man O War Harbor, passing Christmas Tree Island, the mansions on Sunset Key, and Mallory Square from the water. It continues by the Navy Mole and Fort Zachary Taylor, then cruises past the State Park and into the open Atlantic Ocean to watch the day's sunset.
120 min
15 minutes before sailing time - In the Historic Seaport at the corner of Elizabeth and Greene streets. At the ticket booth on the dock along side the Conch Republic Seafood Company Restaurant.
End point
15 minutes before sailing time - In the Historic Seaport at the corner of Elizabeth and Greene streets. At the ticket booth on the dock along side the Conch Republic Seafood Company Restaurant.