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Sunset Sail Cruise in Key West

Overview
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!
City: Key West
Tue 29 Jul
i
You can choose the date already on the booking website
Starting at $91.38
Tue 29 Jul
Starting at $91.38
Make a reservation
What's Included
Coolers of ice with cups and bottled water
Snacks
Sunset Sail
Additional Info
  • 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.
Traveler Photos
Reviews (210)
JudgeCEW
Mar 2022
Enjoyed the view of the schooner from the seats aft of the main sail. Crew very friendly and informative. A beautiful and relaxing evening.
Response from Host
Mar 2022
You all were sitting in the King and Queen seats! Great view of the Rover and the activity. Thanks a lot for sailing with us. We really appreciate your choosing the Rover. Was great having you with us. Hope to see you onboard again, Thank again. Bill Malone - Owner of the Rover.
Kristidee50
Mar 2022
This is my second time on the Jolly Rover and both times it was spectacular. The crew is friendly and accommodating. The ship is never overbooked like a ā€œcattle-boatā€ and you have plenty of room to move around. The captain lets you take a turn at the wheel and photos. It’s definitely something to experience while in the Keys.
Response from Host
May 2022
Glad to read that you had a great time on both sails with us! And that you liked the Rover and our crew! Thank you very much for this review! The Rover is very easy to move around on - and we are fortunate to have a wonderful crew who handles the boat and can still be available to assist our guests. We look forward have you join us again when you return to Key West. Thanks for choosing to sail with us. Sincerely, Bill Malone
SchlodiHamburg
Oct 2023
It was our fourth time on board. It was wonderful as always. A very quiet and relaxed tour without loud music.

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