Linda M.
8/17/2025
What a fantastic sailing cruise and sunset!!! The Jolly Roger captain and staff made the sailing interactive with ALL guests with cheerful conversations, letting guests help lift the sails,...
Schooner Jolly II Rover
Closed
(59)
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631 Greene St
Key West, FL 33040
The Tall Ship Schooner Jolly II Rover is the most photographed ship in Key West! A top Key West attraction is the Rover's famous "Red Sails in the Sunset" two hour sail. With its distinctive red sails and being the only square rigged tall ship in the Historic Seaport, the Jolly II Rover is the focal point as it sails past Mallory Square every evening. The voyage takes you back in time on a classic 80' topsail schooner to an era of pirates, rum runners and privateers seeking freedom and adventure. Their spirit lives on the Jolly II Rover. Come join in on this experience, help raise the sails, fire the cannons and take your turn steering this magnificent ship! The Tall Ship Schooner Jolly II Rover is an exciting, traditional sailing experience with a hint of Piracy! - - - YES, WE HAVE CANNONS!
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Reviews
5.059 reviews
Laurie V.
5/8/2024
My husband booked us on this sunset cruise. We wanted a lower keyed experience and it was perfect. This tall ship does not serve alcohol or food only water and snacks. The positive side is you get...
michelle
8/3/2025
My husband and I decided to board for the sunset tour and it did not disappoint!!!! It was our best experience ever (we have been on sunset tours on other vacations). This by far was the best...
Just A Girl I.
7/11/2024
We have sailing with these guys since 2016. Every time we are in town, we love to hang with them. This is the best value and sailing tour in Key West!
Kirby S.
7/7/2024
Over priced, Great concept but dry toast experience. Nice crew, no refreshments. Turned out to be only a boat ride
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