Sunset Sail Cruise in Key West
4.9 / 5 · 296 traveler reviews




Sailing on the Rover is an exciting, traditional sailing experience with a Hint of Piracy! Yes - We have cannons! Come sail on Key West's most photographed ship! The Schooner Jolly II Rover is the only squared rigged, topsail schooner in the Historic Seaport! It is Key West's famous "Red Sails in the Sunset" Tall Ship! There is no band playing or loud music. We go sailing! Plenty of room to get up and mingle with other guests. Help raise the sails! Steer the ship! Shoot the cannons! Or just sit back and relax!
Your experience
Stop 1
You will take in a memorable sail of Key West's most famous sights - the Historic Seaport of Key West - cruise into Man O War Harbor - sail by Christmas Tree Island - the mansions on Sunset Key - see Mallory Square from the water - the Navy Mole and the Civl War Fort Zachary Taylor - cruise by the State Park and sail out into the open Atlantic to observe each days unique sunset!
What’s included
- Coolers of ice with cups and bottled water
- Snacks
- Sunset Sail
Not included
- Alcoholic beverages
- Carbonated beverages
Meeting and pickup
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.
Before you go
- Infants and small children can ride in a pram or stroller
- Service animals allowed
- Public transportation options are available nearby
- Infants are required to sit on an adult’s lap
- Suitable for all physical fitness levels
- There is no wheelchair ramp but we will do out best to accommodate wheelchair passengers.
Cancellation policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
Check the policy for your selected date and option before booking.
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