Key West Sunset Sail: Traditional Pirate Experience
4.9
175 Ratings
Key West
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: 1 day learn more
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 music or live bands. We focus on sailing! Ample space for socializing with fellow voyagers. Participate in raising the sails! Take the helm! Fire the cannons! Or simply kick back and take it easy!

  • There is no wheelchair ramp but we will do out best to accommodate wheelchair passengers.
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
(175 Ratings)
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Susan_p
Apr 16, 2024
Awesome sailing experience - First time in Key West and my son planned this trip for us. It was perfect. Gorgeous weather and our first time on a sailboat. It was amazing. I would highly recommend this excursion for anyone who wants a relaxing sunset experience on the water. Watching the staff shoot the canon was fun too! Crew was awesome!
Review provided by Viator
O7716vshollyr
Apr 13, 2024
Beautiful Sunset Cruise - We went on the tour the first week in April. The crew and captain were so friendly and knowledgeable. There was very little wind that evening, but that put the sails up and caught the wind, and took us out for a nice cruise. Then we stopped and watched the outstanding sunset. We will definitely do this again.
Review provided by Tripadvisor
Erin_f
Apr 10, 2024
Great time. - Lots of fun. I would recommend this trip for families or couples that want to be on a beautiful boat. They let the kiddos have a turn sailing it. What fun.
Review provided by Viator
Kourtney_t
Apr 10, 2024
It’s the perfect romantic... - It’s the perfect romantic date or wedding proposal having the sunset and getting to propose in the captains spot and they helped by taking our picture it was amazing everyone one was super sweet and helpful
Review provided by Viator
Kourtneyt833
Apr 10, 2024
Perfect proposal is the captains spot at sunset - We had a great time with beautiful views! And the staff was super cool and friendly they even helped me make the perfect wedding proposal in the captains spot and the staff took great pictures for us too ❤️ thank you guys so much we will remember it forever!
Review provided by Tripadvisor
Lotwaites
Apr 8, 2024
Great Harbor Experience - We had a great time! The team was engaging, hardworking and attentive. We have traveled all over the world, this was probably the best harbor sunset we’ve seen. They guided us to the right spot.
Review provided by Tripadvisor
W2421lqalyssak
Mar 24, 2024
Fantastic time! Great for all ages! - We booked this on a whim having read zero reviews (we met one of the Captains on the dock while walking around). We had kids with us and didn’t want a “booze cruise”. This sunset sail was incredibly family friendly (but great for all ages).Plenty of seating, bathrooms, and we got to sail! The pirate aspects to it were a ton of fun. They shot off canons at other boats - the kids we were with loved it, but it is loud for any sensory-sensitive people. The crew was amazing and friendly. So glad we did this and would absolutely do it again!
Review provided by Tripadvisor
Alexmw3752mq
Mar 12, 2024
Fun time for the family - We were going to do the glass bottom boat cruise but the reviews weren’t that great and the Schooner Jolly Rover kept popping up in those reviews as a better experience. The ship and crew are great. Very friendly and it’s cool to watch them work the sails as a team.
Review provided by Tripadvisor
T1961kujamest
Mar 10, 2024
Great experience! - This is a great excursion! The crew was friendly and engaging. The sunset was beautiful, and the cannons were exciting!
Review provided by Tripadvisor
Carlyle_h
Mar 13, 2024
Enjoyable evening with a... - Enjoyable evening with a friendly crew. They took time to talk with guests, answer questions and make sure everyone was ok and having a good time. The cannon shooting was fun. Saw some dolphins, no sunset because it was cloudy but a nice ride anyway.
Review provided by Viator
Select Date and Tickets
up to 15 guests
1 Adult
May 2024
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