Sailing
2 hours
Free cancellation
Not sure? You can cancel this reservation up to 24 hours in advance for a full refund.
Recommended by 99% of travelers
99% of reviewers gave this product a bubble rating of 4 or higher.
from
$92
per adult
Schooner Jolly II Rover
Schooner Jolly II Rover
5
12:00 AM - 11:59 PM
Monday
12:00 AM - 11:59 PM
Tuesday
12:00 AM - 11:59 PM
Wednesday
12:00 AM - 11:59 PM
Thursday
12:00 AM - 11:59 PM
Friday
12:00 AM - 11:59 PM
Saturday
12:00 AM - 11:59 PM
Sunday
12:00 AM - 11:59 PM
Full view
About
The Tall Ship Schooner Jolly II Rover is the most photographed ship in Key West! A top Key West attraction is the Rover's famous "Red Sails in the Sunset" two hour sail. With its distinctive red sails and being the only square rigged tall ship in the Historic Seaport, the Jolly II Rover is the focal point as it sails past Mallory Square every evening. The voyage takes you back in time on a classic 80' topsail schooner to an era of pirates, rum runners and privateers seeking freedom and adventure. Their spirit lives on the Jolly II Rover. Come join in on this experience, help raise the sails, fire the cannons and take your turn steering this magnificent ship! The Tall Ship Schooner Jolly II Rover is an exciting, traditional sailing experience with a hint of Piracy! - - - YES, WE HAVE CANNONS!
Tours and Tickets by Schooner Jolly II Rover
Travelers talk about
Contribute
Most Recent: Reviews ordered by most recent publish date in descending order.
Detailed Reviews: Reviews ordered by recency and descriptiveness of user-identified themes such as wait time, length of visit, general tips, and location information.
Popular mentions
5.0
1,308 reviews
Excellent
1,247
Very good
46
Average
8
Poor
3
Terrible
4
flg
Plano, TX7 contributions
Dec 2019
If you love tall ships, do not miss this one. On the day we went it was unusually windy so only three sails were hoisted, but it was fantastic. The captan and the crew were excellent, even served snacks and water on board and answered my dozen questions about sailing. It was a good mix of families and individuals. My adult son and I took the sunset sail because it fit our schedule. Never mind the sun - it sets every day - but a tall ship schooner? There's nothing better.
Written January 10, 2020
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Footprints739815
17 contributions
Apr 2023 • Couples
A sunset 2 hour cruise on This tall ship in Key west is one of the best decisions we made on this trip. I can’t stop talking about how wonderful the crew was and what an experience we were treated to. This sunset cruise was the highlight of our trip. The crew went out of their way to make sure we had wonderful sunset views. Watching the skilled crew operate this amazing 9 sail sailboat was worth the price of admission alone. Plus being on the Atlantic Ocean with the wind filling all the sails and the breezes so beautiful was an experience we won’t forget. The icing on the cake was seeing dolphins fly and arc out of the water along the jolly rover. This was an amazing ride!! Don’t miss the chance to sail this schooner.
Written April 20, 2023
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
shannan s
13 contributions
Oct 2021 • Couples
We took the sunset cruise on the Jolly Roger with some friends and we’re glad we did! The crew was great and very friendly. This is a not a party boat with loud music - it’s a tour to take if you love to or want to be on a sailboat and enjoy the peace of the ocean. The crew was entertaining and gave us some history of the keys. They took some fun shots at boats approaching as if we were being chased by pirates and fired off a cannon at the end of the trip. Bring a bottle of wine and watch the sunset on this schooner and imagine you are transported back in time.
Written October 13, 2021
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
trav115
West Virginia192 contributions
Sep 2021
If you want a REAL sailing ship that provides excellent sunset views on the water that is peaceful and quite as opposed to loud and obnoxious then this is the cruise for you! You are encouraged to bring your own beverage, they do provide water however. You will have a wonderful time sailing on the water and watching the sunset. You might even get to see them firing off their "pirate cannons".
Crew was very pleasant, they will let you help with raising the sails, steering the boat ect if you want, we just opted to sit back and relax.
By far the highlight of our trip to Key West, my only regret is that we didn't do this more.
Crew was very pleasant, they will let you help with raising the sails, steering the boat ect if you want, we just opted to sit back and relax.
By far the highlight of our trip to Key West, my only regret is that we didn't do this more.
Written October 7, 2021
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Thomas T
Key West, FL27 contributions
Jul 2021 • Family
Okay, so we got to Key West and we wanted to do a sunset cruise, not one of the booze cruises, but a true relaxing cruise with a sunset. WE GOT WHAT WE WANTED AND MORE!!! We have been to Key West on the cruise ships and always saw the sail boat with the red sails and this time we were on that sail boat!!! The Captain and crew are awesome and really made it fun, our youngest got to drive the boat. Yep it also has a cannon that they fire at the end of the cruise!! This is a true sail boat experience with no engines running! The crew is very knowledgeable of the area and told stories and pointed out features of the area. If you are wanting to get away from the crowded other cruises that pack the people on like sardines, have loud music, and craziness, then this is the cruise to take!! Book this early as it is a limited amount of people.
A special thank you to the crew for a memory that we will always talk about!
A special thank you to the crew for a memory that we will always talk about!
Written July 9, 2021
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
sharon k
5 contributions
Apr 2021 • Couples
This was a lovely sunset cruise. The red sails really stand out in this beautiful ship. The crew was friendly & relaxed, setting the tone for the passengers to just chill & enjoy the ride with the ability to get up and mingle with the other guests- or not. It is a BYOB cruise, but there’s a large cooler on board to store your booty. If you ever want to steer a tall ship or help raise the sails, you can get the experience here. There’s even a cannon on board that “shoots” at other boats in the harbor. At the end the display what they call rolling thunder where they shoot the cannon at the shore & the echo reverberates back.
Written April 11, 2021
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Chiara E
2 contributions
Jan 2020 • Couples
Today me and my girl went on their sunset tour. We definitely recommend this. The staff is super friendly and very relaxed. You pay a few bucks more than with some others but in return you get a non-overcrowded tour with small snacks and ice coolers with fresh water or to cool your own drinks.
The information and experience they have is incredible and so is the sunset. We loved it! 5/5
The information and experience they have is incredible and so is the sunset. We loved it! 5/5
Written January 5, 2020
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
AMWohio
Cleveland, OH6 contributions
Oct 2020 • Family
Outstanding evening trip to sea, maties! Fun, lighthearted and hard-working crew took us out for a 2 hour sail to watch the sunset. The captain is a vibrant story teller, in the best tradition of sailors. 10 sails total of which we only had 4 up, but got moving at a good clip. Much to the joy of all aboard, they boat sports an array of canons and took the opportunity to fire them off against passing frenemies!
Written October 18, 2020
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Jenny S
Lawrenceburg, IN11 contributions
Oct 2023 • Friends
What a fabulous sunset experience. Once aboard you know you are going to be a part of a must do again cruise. Watching the small crew hoist the sails and set sail toward the beautiful sunset, with no music, snacks, water, and the pleasure of interacting with the crew, was exactly what they promised. With a limited number of passengers, it made it so easy to engage with the other passengers to share this incredible schooner. The firing of the canon, let your imagination allow you to be a pirate for the evening. By far, it was one of the best excursions I have chosen.
Written October 23, 2023
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
arthurbanga
West Hartford, CT89 contributions
Sep 2021
This schooner has gorgeous dark red, almost copper color sails. Amazing amazing staff, a great ride, great guide, plenty of cool beverages, water, plenty of space. A sunset cruise is simply like a fair story. We enjoyed every second on the night of Sept 1. They value each customer, and everybody obviously had a great time.
Written September 7, 2021
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Who is BobbyB? Can he help with a snorkel/sandbar excursion for 10 adults?
Written July 18, 2021
The Jolly II Rover lets the Boy Scouts use the ship 5 days a week during the months of June, July, and August. We offer Sunset sails on Friday and Saturday nights only, up till the last week of August.
Written June 28, 2017
Are drinks or food available on the sunset cruise?
Written March 26, 2017
We provide a lite snack of assorted crackers and cheese, fruit and veggies, and bottled water. You are free to bring anything you want to eat or drink. BYOB. We supply the cups, ice, coolers, and corkscrews.
Written June 28, 2017
What time do you need to be there for the 6:15 sunset cruise?
Written February 18, 2017
We got there about an hour early and sat at the bar next to the dock.
Written February 23, 2017
Robert G
State College, Pennsylvania
What are your operating hours? Do you sail weekdays?
Written July 14, 2015
They sail afternoons and evenings most days
Written May 27, 2016
Showing results 1-8 of 8
*Likely to sell out: Based on Viator’s booking data and information from the provider from the past 30 days, it seems likely this experience will sell out through Viator, a Tripadvisor company.