Key West Sunset Sail: Traditional Pirate Experience

Embark on a thrilling sunset sail on the Rover, Key West’s famous ‘Red Sails in the Sunset’ Tall Ship. Experience traditional sailing with a hint of piracy. Cannon firing included!

Duration: 2 hours
Cancellation: 24 hours
Highlights
  • Schooner Jolly II Rover - 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
What's Not Included
  • Alcoholic beverages
  • Carbonated beverages
Additional Information

Embark on a thrilling and classic sailing voyage with a touch of pirate adventure on the Rover! Guess what - We even have cannons! Get on deck of Key West’s most snapped ship! The Jolly II Rover schooner stands apart as the only square-rigged, topsail schooner in the historic harbor! Known as Key West’s famed ‘Red Sails in the Sunset’ Tall Ship! No loud…

Location
631 Greene St
Greene Street
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.
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Customer Ratings
4.9
(213 Ratings)
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Archie_w
Mar 11, 2025
Sunset - This is a low key beautiful way to experience the beauty of the Keys offshore. The staff were so genuine and kind.
Review provided by Viator
Joelatravels
Mar 2, 2025
This was a quiet sunset cruise on a beautiful sailing ship. We had sails in the wind minutes after leaving port. - Jonathan and the crew were great! We watched many other “sailboats” motor on by - not sure what their idea was with that. No loud music. BYOB - much more economical and we had one of our own favorite wines.
Review provided by Tripadvisor
Elizabeth_hesler
Feb 27, 2025
Fantastic cruise aboard a sailing ship - We had a wonderful experience! The ship is beautiful. The crew, including the ship’s owner, were incredibly friendly and personable. They were a lot of fun and made us feel like we were all part of the crew. They clearly love what they do. The cruise was relaxing and peaceful, exactly what a sunset cruise should be. We will definitely sail with them again.
Review provided by Tripadvisor
Marc_g
Feb 24, 2025
What a choice! What a... - What a choice! What a perfect sunset sail for a sailor. Want to surprise her to celebrate anything, even just being together, this is it.
Review provided by Viator
Rebecca
Feb 24, 2025
Jolly Trip - We had a wonderful trip on this schnoor. The crew were very personable and made sure we were comfortable and enjoying ourselves. They offered to let us help on board if we wanted and even steer. The hint of piracy was fun too as were the little cannons. It was a beautiful evening and sunset. We would definitely do it again. There were only about 25 of us that night so it’s nice that the trips are not o we crowded. We brought a bottle of wine to enjoy.
Review provided by Tripadvisor
Ducedoc
Feb 22, 2025
Great Experience - We had 10-13 mph winds so the sail was invigorating. Sunset cooperated, got lots of pictures of selves, Key West, neighboring boats and sunset. Picturesque boat with helpful and fun crew, so overall a great experience.
Review provided by Tripadvisor
L7423jzrobinm
Feb 17, 2025
Small but lively, wonderful sunset sailing experience - Awesome time! Captain and crew are fantastic. Loved the cannon fights! Loved that my husband and son got to assist with hoisting the sails! This was our (husband and I) first time on this cruise, my son and his wife have been on this three times, and my daughter and her husband twice. We will all be back again, for beautiful sunset views, laughter and memories! Perfect evening sail in Key West!
Review provided by Tripadvisor
Unionmama
Feb 16, 2025
Amazing! - I can't begin to put in writing how wonderful this cruise was! The crew of Carl, Tom and Rachel were so much fun, entertaining, and informative. The owner, Bill, was on board also and made a point of personally speaking to each person there. The sunset was gorgeous. Would do this again in a heartbeat!
Review provided by Tripadvisor
Retepger
Feb 13, 2025
Great way to end the day! - This is such a fun and relaxing cruise! The crew was super attentive and friendly! There’s a bit of piracy too and a four legged first mate! Sunset was gorgeous! The crew made sure we got the full experience!!
Review provided by Tripadvisor
Leslie_c
Feb 5, 2025
Very nice sail with a... - Very nice sail with a great crew. Also get to see a cannon being shot off. We had an added bonus of dolphins putting in a show.
Review provided by Viator
Select Date and Tickets
up to 15 guests
1 Adult
April 2025
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