Key West Sunset Sail: Traditional Pirate Experience
4.9
244 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: 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…

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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
(244 Ratings)
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1 star
Rachel
Oct 30, 2025
Simply magical - I smiled as I stepped on board and didn’t stop smiling the whole evening. The entire experience was simply magical, the crew friendly, welcoming and informative. We were lucky enough to have the owner on board last night and it was such a pleasure to meet him. This is no party boat (thank God), but a beautiful schooner, the only sound you need is the sound of her cutting through the water and good conversation with those on board, plus the chance to take the wheel yourself for a few minutes - under expert instruction of course! We loved every minute and haven’t stopped talking about it since, an experience we will treasure forever- thank you!
Review provided by Tripadvisor
Inspire05161523870
Oct 7, 2025
Don't miss - The crew were great. Very friendly very helpful. Would recommend to any and everybody. Perfect for the family if you're looking for a party boat with loud music and watered down drinks this is not it if you're looking for a great sail with knowledgeable people then buy your ticket
Review provided by Tripadvisor
Tara_s
Oct 3, 2025
Really nice boat,... - Really nice boat, beautiful sails. Unfortunately there wasn't a lot of wind that day so we didn't get to see it in full action.
Review provided by Viator
Netforceone
Sep 6, 2025
Loved the Sunset Cruise Aboard the Jolly II Rover - This was the perfect sunset cruise. The captain and crew were great, keeping all passengers engaged. I got to help raise the sails, and another passenger helped steer the ship. The cruise was relaxing, fun, and entertaining. I highly recommend and will definitely join for a future cruise when I return to Key West.
Review provided by Tripadvisor
Lindamb2153ou
Aug 17, 2025
Fantastic, relaxing and interacting sunset cruise - A fantastic sunset cruise in Key West. The Captain and staff were great with interacting with the guests including them in raising of the sails, conversation, allowing time at the helm and bring down the sails. There were various points where cannon shots were sent to other boats along with on shore outside restaurants. Couldn’t have been a relaxing and calming sail.
Review provided by Tripadvisor
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
Check Availability
From $95
From $95
up to 15 guests
1 - Adult
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Cancellation: Free cancellation up to 24 hours before the start of your experience (local time).