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
(267 Ratings)
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Denise_r
Jan 20, 2026
Great sunset sail with... - Great sunset sail with good food, friendly crew, and an overall wonderful experience! Highly recommend, you will enjoy!
Review provided by Viator
696adamtt
Jan 15, 2026
Relaxing and fun! A true sailing experience on a beautiful boat. Not a booze cruise. - The sunset was amazing from the boat, but honestly the trip would be worth it even on a cloudy day! The captain and crew are genuinely kind and fun and very professional. This is our third time doing this sail over the last 15 years and was definitely a highlight of our week here. Not a booze cruise! This is a chill experience and I highly recommend it. As a side note: our 19 yo daughter has cerebral palsy uses a manual wheelchair and that wasn’t a problem at all. They helped get her on and off the boat, so just go for it!
Review provided by Tripadvisor
Kent_p
Jan 12, 2026
This crew focuses more on... - This crew focuses more on your experience than others I have been with. Others are more "party" boat. This crew was having fun actually sailing and talking with passengers.
Review provided by Viator
Chilt0nn
Jan 3, 2026
Very enjoyable trip which my wife and I still talk about. - The captain and crew were just really nice. I did a sunset sail, and would recommend the trip to anyone. I have recommended it to family if they go to the area. The crew let me help raise one of the sails, which even as an adult really added to the experience.
Review provided by Tripadvisor
X4409zkandrewp
Dec 24, 2025
Family Set Sail - This was a great experience. I brought on board my 1.5 year old and 3 year old and the crew let them at the helm, which was a great experience. The crew was especially personal, friendly, and helpful. I give the experience 10/10 and when I’m in key west again, I will take my family again.
Review provided by Tripadvisor
Explorert
Dec 21, 2025
Much better than the regular catamaran cruises - Amazing experience…. The crew was great… we loved chatting with Veronica… It was so much better than the regular catamaran cruises..
Review provided by Tripadvisor
Richard_t
Dec 12, 2025
Chit chat - Chatted with the owner for a good portion of the sail...lot of great information. My girlfriend was equally impressed with him and the crew
Review provided by Viator
Janelleh991
Nov 29, 2025
Great experience and so fun!! - One of our favorite Key West experiences and traditions! We had a family party of 8 from ages 4-80 and we all had a wonderful time! Captain Tom and his crew are so kind and attentive- especially to the small kids and the crew included them for hands on Experience. Plenty of priceless family photo opportunities. Quiet and cozy way to watch the key west sunset and experience a gentle family friendly sail- worth every penny! Thank you all and owner Bill who went out of his way to chat with everyone on the schooner!
Review provided by Tripadvisor
Robert
Nov 29, 2025
The perfect cruise to experience the ocean and the extraordinary sunset. - It was exactly the cruise we were seeking. The schooner was beautiful. The crew was skilled, friendly and considerate. The sunset was stunning. This is NOT a party cruise. This is the perfect cruise to enjoy the ocean and the sunset more quietly. We can’t recommend it highly enough .
Review provided by Tripadvisor
Thomas_j
Nov 23, 2025
Outstand crew - It was awesome and highly recommend. The crew was very fun yet professional. They where knowledgeable and answered every question we had. Its a cruise that didnt need drinks or food to make it ejoyable.
Review provided by Viator
From $95
up to 15 guests
1 - Adult
Cancellation: Free cancellation up to 24 hours before the start of your experience (local time).