Sailing on the Rover is an exciting, traditional sailing experience with a Hint of Piracy! Yes - We have cannons! Come sail on Key West's most photographed ship! The Schooner Jolly II Rover is the only squared rigged, topsail schooner in the Historic Seaport! It is Key West's famous "Red Sails in the Sunset" Tall Ship! There is no band playing or loud music. We go sailing! Plenty of room to get up and mingle with other guests. Help raise the sails! Steer the ship! Shoot the cannons! Or just sit back and relax!
Posted By : Robert_B
Amazing sunset cruise. Everyone from, Bill the owner, Rachel the Captain, Chris the deck hand and all of the deck hands were kind, courteous, informative and made our trip phenomenal! From firing the canons to watching the amazing sunset, we had an amazing experience and will definitely be back!
Rating :
Posted On : 2024-06-29 10:49:14 
Posted By : E9919NFsophial
The crew on ship were just the sweetest! We were allowed to steer the ship and cast the sails, there was even a canon they fired whenever a ship went by which was always super exciting. We even got to see a the sun having a green flash which the owner pointed out for us! 100%recommend if you ever go to Key West, was the highlight of my vacation.
Rating :
Posted On : 2024-06-22 21:57:46 
Posted By : CrazyHalfs
This was our 4th sunset sail on the Jolly Rover and they did not disappoint. The sunset was not the most vibrant one we’ve ever seen but the winds made for a fantastic sailing experience. The crew is always efficient and do everything they can to make it a fun trip for all on board.
Rating :
Posted On : 2024-06-22 20:42:46
Posted By : BuzzF976
My wife and I recently returned from our seventh annual trip to Key West. Since the first year, we discovered the daytime and sunset cruises on the Schooner Jolly Rover. Since our first sail, we have sailed 2 or 3 times with each visit. WE LOVE IT! No two trips are the same. It is so peaceful and quiet, while under sail, you can almost hear the sun splash into the sunset. The crew is very knowledgeable and very welcoming. They seem to be having as much fun as we are. Truly looking forward to next year's trip to Key West and multiple sails on the Jolly Rover. To Bill and his great crew, thank you!!
Buzz & Janet F.
South Windsor, CT.
Rating :
Posted On : 2024-06-05 23:22:12
Posted By : Sightseer64733437743
5 stars! We picked this cruise from the TripAdvisor reviews. It was awesome. The crew was amazing and so friendly. They were great with the kids onboard. There were about 25 people on this tour. We stopped to watch dolphins and the sunset. The best part is the crew shooting off the cannons playfully at other boats. (don't worry, no cannon balls!) A fun and relaxing trip!
Rating :
Posted On : 2024-05-24 22:22:01
Posted By : Adventure11979660720
If you're looking for a non-party type relaxing sunset cruise in Key West - look no further - this is the sunset cruise for you! My partner and I celebrated our 20th anniversary on the Jolly II and we had the best time! The crew engaged us by allowing guests to hoist the sails and steer the schooner into the sunset. Also, the cannon blasts along the route were so fun! This is a BYOB and snacks cruise which was great, too. We put together a small charcuterie box and enjoyed ice cold Pear cider. The Schooner Jolly II Rover crew are amazing!! Highly recommend!!
Rating :
Posted On : 2024-05-20 12:08:14
Posted By : jruiz305
Returning guests-Always have a great time on board! The crew is amazingly friendly and really attentive. You can bring your own snacks and libations and they are great at always keeping your glass full. They also offer to take pictures at sunset and we have beautiful memories each time. The cannon is super fun for the young little pirates too! Highly recommended!
Rating :
Posted On : 2024-05-18 18:30:06
Posted By : LINDA_N
Wonderful crew, sailing ship and exciting experience! They made us feel comfortable and at home at sea and made my granddaughter's birthday celebration a precious memory. We wanted to stay longer than two hours! What a beautiful experience! We will certainly come back every year.This will be part of our family tradition!
Rating :
Posted On : 2024-05-15 19:12:33
Posted By : deborahfM4471CM
Absolutely wonderful! The crew was courteous and informative. They had someone in training, so it was fun listening to their instructions. We brought a bottle of wine to celebrate our anniversary, and enjoyed a peaceful evening with warm winds, a stunning sunset, and great conversation. We sat next to the ship’s owner who shared the history of the ship, and another couple also celebrating their anniversary.
This was our second time sailing on the Jolly II Rover, and we’ll back again next time we’re in Key West!
Rating :
Posted On : 2024-05-14 07:30:25
Posted By : Kathyjb1011
The Jolly River is always a MUST DO during our stays in Key West! We have tried others over our 40+ years of visiting and settled on this incredible experience. The captain and crew make the Sunset Cruise relaxing, fun, and interactive. You will get the opportunity to hoist a sail and do a photo op at the helm with pirate hat and sword to boot! They encourage ranting to other sunset cruises with cannon shots back and forth. Yet when the sunset is the star, and the engines are quiet it is a surreal experience. Crew is always available to take those memorable photos of you and your group and serving you water and your drinks you brought on board. There is not a bad seat on this cruise (saw some cattle boats where most passengers had to stand). This is an incredible way to highlight a day in the beautiful waters of Key West!
Rating :
Posted On : 2024-05-13 10:39:27
