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 an exhilarating journey aboard the Rover, where traditional sailing meets a touch of piracy! Indeed, there are cannons on board! Set sail on Key West’s most photographed vessel, the Schooner Jolly II Rover, the only square-rigged, topsail schooner in the Historic Seaport. Known as Key West’s iconic “Red Sails in the Sunset” Tall Ship, this…

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
(276 Ratings)
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Janelle_g
Apr 11, 2026
Lovely sunset sail - Lovely sunset sail. Not a noisy party boat but a peaceful sail as the sun set over Key West. Highly recommend!!
Review provided by Viator
Emily_b
Apr 5, 2026
Relaxing evening - We had a wonderful, relaxing time aboard the Jolly Rover. The captain and crew were welcoming, friendly, and fun. The ship was beautiful and it was very interesting to watch the the sailors do their thing.
Review provided by Viator
Snackattack6
Mar 30, 2026
10/10 would recommend - 10/10. Crew was extremely nice and knowledgeable. Sunset was amazing. They let our son pull up one of the sails which was a unique experience. Also the cannon was shot after sunset and it was truly amazing at night. Def worth the $$.
Review provided by Tripadvisor
Bob_b
Mar 30, 2026
A relaxing sail out to... - A relaxing sail out to see the sunset. The crew was very friendly and we had a great time. Would again.
Review provided by Viator
Bholaw
Mar 23, 2026
Smaller, intimate cruise - Want an alcohol/cramped atmosphere, this isn't it. Want a relaxed sunset cruise with a great captain and crew, do this. We had a great time. The ship was stationed in a great position to view the sunset. They were not rushed. We were one of the first boats out, and the last boat in. The setting was more intimate where you had time to speak to your fellow cruisers, and the number was great.
Review provided by Tripadvisor
Teresake6533qf
Mar 21, 2026
Perfect sunset cruise - A relaxing evening on the schooner jolly II Rover. Casual atmosphere. Crew were experienced sailors who answered questions and gave passengers a real taste of sailing and how it must have been during the time of the tall ships. Gorgeous sunset. Would highly recommend.
Review provided by Tripadvisor
Curtis_d
Mar 16, 2026
"Green Flash" on a perfect sunset - We were looking for a sunset cruise that did not market towards the "booze cruise" crowd, and this was it. You can bring your own snacks or drinks, as the crew does not provide alcohol on board. The crew were all very engaging and took the time to meet all on board and thoroughly explained the itinerary. We could not have been happier, between the beautiful sunset, smooth sailing, and wonderful crew. We would 100% recommend.
Review provided by Viator
Steve_l
Mar 12, 2026
this experience was... - this experience was absolutely amazing! i would highly recommend taking this schooner sail boat tour.
Review provided by Viator
Jill
Mar 11, 2026
Spectacular Sail by Sunset - Very professional captain and crew and beautiful ship. It was a lovely sailing experience and such a great way to view an unobstructed sunset in Key West. Highly recommend!
Review provided by Tripadvisor
Bethanybeachchick
Mar 9, 2026
Great Night with a Great Crew - We had a blast! We went out with eight adults to celebrate a 65th birthday, and had an amazing time. Captain Tom and the entire crew were great. We were lucky to have a beautiful night and fun folks on board. Thanks to all for such a fantastic experience!
Review provided by Tripadvisor
From $95
up to 15 guests
1 - Adult
Cancellation: Free cancellation up to 24 hours before the start of your experience (local time).