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
(240 Ratings)
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1 star
Linda_m
Aug 17, 2025
Fantastic and calming sail and perfect ending with a colorful sunset!! - The ship was a perfect size with about 18 people plus crew. It was smooth sailing and very calming with beautiful views. The crew interacted with all those on board. Some helped lift the sails, children and adults could sit at the helm!! They even shot off a small cannon at a variety of boats.
Review provided by Viator
Katierz5444jh
Aug 10, 2025
Loved it - Trip was wonderful and timely! Crew was friendly and we saw a beautiful sunset despite being cloudy and possibly a stormy night.
Review provided by Tripadvisor
Damon_c
Aug 5, 2025
Very pleasant I love the way the ship sail - Very good 💯 I love the crew very much love atmosphere the culture good experience Love crew very quiet and pleasant
Review provided by Viator
Kathleenhn6981em
Aug 5, 2025
The best experience of our Key West vacation - This was a wonderful cruise! The crew was super friendly and made us feel welcome. They engaged my son and husband to help with the sails, and had other passengers help steer the boat, which was so fun. They heckled other boats and pretended to shoot at them with loud cannons, which was hilarious, especially when we encountered a huge yacht. We especially enjoyed that at sunset they cut the engine and allowed us to experience the beauty of the colors in the sky in an awed silence. The best experience of our Key West vacation!
Review provided by Tripadvisor
Tanfah
Aug 3, 2025
Perfect sunset - It was the best sunsetcriuse I've ever taken. +small group +friendly, fun and helpfull crew +beautiful sunset view +I could help to put the sails up and could go behind the wheel
Review provided by Tripadvisor
Kpg0422
Jul 12, 2025
Amazing sail, amazing crew! - Amazing sail, amazing crew! The crew had our teen boys help raise the sails which was so cool. The crew was friendly and shared their knowledge of the boat, the area, and Key West in general. They had water and snacks for us. Would highly recommend!
Review provided by Tripadvisor
899sethm
Jul 8, 2025
Leisurely Sail - My family enjoyed a great evening cruise. The water was beautiful.. The staff was particularly attentive, and my kids even helped to steer the boat. I highly recommend this trip for everyone visiting Key West.
Review provided by Tripadvisor
Chris_c
Jul 6, 2025
Nice sunset cruise with sailing lessons - It is fun and you get to learn a bit about sailing. No cannons on our trip but was still very cool and peaceful.
Review provided by Viator
Bordelon777
Jul 1, 2025
Great Experience on a REAL Sailboat!! - My family of 4 thoroughly enjoyed the sunset cruise aboard the Jolly Rover. The crew and captain went above and beyond by visiting with their guests and providing fun and entertainment with the other boats, by blasting their hand-held cannon! My husband got involved with raising the sails and loved the experience. We also appreciated the padded seats and back support while sailing. Highly recommend!!
Review provided by Tripadvisor
Michaelnh1001sm
Jun 23, 2025
Awesome! We will come back. - We had a wonderful sunset sail! The whole crew and the captain were great 😊 We left the Harbour with the engine and the rest we sailed and cruised into the sunset 🌆 Big fun was also the surprise while passing by other sail ships 🏴‍☠️
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).