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Key West Sunset Sail: Traditional Pirate Experience
4.9
227 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!
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!
- 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
- Coolers of ice with cups and bottled water
- Snacks
- Sunset Sail
What's Not Included
- Alcoholic beverages
- Carbonated beverages
- 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…
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.
For a full refund, cancel at least 24 hours before the scheduled departure time.
Customer Ratings
4.9
(227 Ratings)
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Sassyred68
Jun 2, 2025
Wonderful couples sail - Beautiful evening for our sunset cruise. The crew were very friendly and made a point to visit with each group. Free water and chips passed around but you can bring your own drinks and snacks too. Boat is a reproduction but it felt historic. We had a great time with the smaller group of people and no loud music made for peaceful sailing. Highly recommend.
Review provided by Tripadvisor
P610orsherryh
May 30, 2025
Highly recommend! Amazing schooner and crew! - We were sold on this particular sunset cruise because of the smaller group number (the max number of people is 40ish I believe) and the hint of piracy! This schooner allows you to relax and enjoy the ride as there is not loud music blaring during the trip. There were opportunities to help raise the sails, take over the wheel for the captain and enjoy the cannon being shot at other boats. The owner, Bill, is often on the sunset cruises and a wonderful person with many stories to tell. Would highly recommend!
Review provided by Tripadvisor
K
May 28, 2025
Modern Version of the “Black Pearl” - Crew was great! Knowledgeable, engaging and friendly. I’ve done some large boat sailing and this sail boat was new, well kept with views in every direction.
Great evening to watch the sunset and enjoy the views.
They let me control the wheel for a while which made the experience even more enjoyable.
Review provided by Tripadvisor
Sambb1095ng
May 24, 2025
Just sit back smile and enjoy to view!! - I book this cruise every time I’m in Key West. Just the best, most beautiful, and an absolute blast! From the owner, to the awesome captain and crew!! Can’t wait to sail with you guys again soon!!!
Review provided by Tripadvisor
Keltk
May 22, 2025
Amazing Sunset, Awesome Crew! - Captain Bill and his crew not only sailed us into a beautiful sunset, but gave us a perfect sail that was enhanced by their conversations with the passengers about sailing, including asking who would like to help hoist the sails.
As on our 25th anniversary, we celebrated our 40th on the Jolly II Rover and had a fantastic and fun time! You cannot go wrong in choosing to sail with Captain Bill and his awesome crew for an evening you will remember and want to do again—like we did and will do again!
Thank you, Bill and crew!!!
Review provided by Tripadvisor
Staceygw7986sx
May 20, 2025
Sunset & Sea Shanty - My husband & I did the sunset sail on Saturday evening. We were looking for a relaxing, beautiful trip, and Jolly Rover II delivered! It was a beautiful sail out to.see the sunset, with a knowledgeable and fun crew. From cast off to 'firing' at 'enemy ships' to the singing of a sea shanty s we returned to harbor, it was a fun time. Also had the opportunity to learn a bit about sailing in the process! We were looking to avoid a loud, crowded party boat atmosphere, and Jolly Rover delivered the experience we were looking for. Would do it again & definitely recommend if a fun, peaceful sunset sail is the goal.
Review provided by Tripadvisor
V812zztraceyf
May 8, 2025
Sunset sail - We had a wonderful evening sailing on this yacht. We watched the sails being raised and were invited to help ,which we declined but we did both have a turn at steering .The crew were all very friendly ,informative and entertaining especially when playing at being pirates ,firing the cannons at passes by !! IThe sunset was Amazing. I can truly recommend this trip.
Review provided by Tripadvisor
Wander58872061460
May 4, 2025
Wonderful sunset sail! - Wonderful sunset sail. heading out, the crew was very friendly and allowed a couple of us to be deck hands and pull up the sails. snacks and water were plentiful. As a “pirate ship” we hailed other ships and fired a tiny cannon looking for loot. As the sun started to dip we started to drift along serenely and the sky glowed as taps from the navy base wafted over the water. If you are looking for a quiet sail and a sea shanty or two, from Captain Shane, this is a sail you will not want to miss.
Review provided by Tripadvisor
I6428bzivana
Apr 27, 2025
Beautiful old sailing boat ride for sunset. - Very nice experience, friendly and top crew, lots of explanations and interaction. Beautiful sunset and beautiful walk.
Review provided by Tripadvisor
K33gaalexh
Apr 23, 2025
5 stars - It’s down on the right hand side of the restaurant. Last jetty on the right.
You can’t miss this beautiful boat. I did a sunset cruise and it was everything I hoped for and more, you could help with the rigging, steer the boat, very knowledgeable captains and what’s fun crew!
This is THE pirate ship you want. And nothing beats sailing by the wind.
Skilled staff, wonderful people with fascinating stories. Well worth it.
Review provided by Tripadvisor