Awesome Cruise - Great cruise. We had a wonderful time, crew is amazing. Definitely worth the trip and would take it again.

Sunset cruise Dec 2024 - My husband and I decided to take this cruise a couple hours before sailing and was the best idea. The crew was very nice and was great way to see sunset. Loved every minute being on the water.

Perfect - Great trip beautiful sunset Great crew. Timing was perfect To see. the sun disappear into the ocean while cruising The Jolly Rover is to experience a trip under sail and watch the crew hoist and lower the sails with much precision.

Pirate fun! - Fun time was had by all. The crew was fun and the cannon added another level of excitement as we were pirates for the evening!

Nice, cool experience sailing close to Key West pretending to a be a pirate. - Great adventure. Small group fo people, nice plot (pirates), and great experience in Ket West waters. Shots were fired, stories were told. Be a part of Key West history and enjoy the adventure. Chat with the crew. They have lived in the area for a while and can tell you the stories.

Great time! - We had so much fun when the crew fired their cannons at passing boats! Being on the water a sunset was so pleasant and pretty. The crew were very knowledgable and made it a great experience.

Hoist the Black Flags - So our excursion was quite the adventure. We were in town for our youngest son’s make-a-wish trip and this was one of his planned excursions. From the time we arrived at the check-in booth the staff was very welcoming and friendly. Once we boarded we were welcomed and made to feel very special which while our son was bashful, he did appreciate as did my wife and I along with our other two children. So for us and our son, while he did get to ride a “pirate ship”, sit in the Captains Seat and “steer the ship”, and see canons being fired, our actual trip was cut short due to a microburst (storm) that rolled in unplanned. The Captain was watching for inclement weather that was south of us but that burst that came through was unexpected and quite strong and we had to drop sail and return to port, but not before the captain navigated to calmer waters and the crew were able to fire off the canons and yell pirate obscenities (Kid friendly so don’t worry) at other watercraft and navy personnel at the Navy Base. Our daughter was scared when the boat started rocking pretty hard when the wind picked up but the crew were attentive to her and did try to assure her that everything was okay and was nothing to at they hadn’t handled before. (Thank you to the crew for that). Our youngest son held his sword in the air and let out a good Arrg! when we were rocking and rolling in the storm for a moment. Everyone was very apologetic for the uncooperative weather and offered refunds/reschedules to everyone which we thought was very nice of them and we really did try to make it back out the next night as we were welcomed back, but our little one was exhausted from his long day and we couldn’t make it back out. It was a wild ride, but we have an awesome story to tell and our son had fun! So, to the Captain, Crew, and Owner, thank you very much for making us and more importantly our son feel special, if only for a little while and giving him a trip that he will remember forever. We now joke that he’s a real pirate as he braved his first storm at sea. So thank you again and best wishes to you all.

Awesome Sunset Cruise - There is no better way to experience the glorious Key West sunset than to sail on board the Schooner Jolly II Roger - and sail was the operative word! Skillfully guided by the wonderful crew under full wind power sail in the waters off Mallory Square this was two hours of wonderful relaxation, sightseeing and fun. Set in the era of the pirates, patrons are invited to participate in setting the sails and firing the cannons. While water and small snacks are provided, this is essentially a bring your own food and drink (including alcohol) adventure, therefore you can bring along food items and refreshments that suit your own taste. Highly recommended.

A pleasant, "low key" Sunset Cruise - This was one of the highlights of our trip. The owner, and crew could not have been mor accommodating. We wanted a laid back sunset cruise and these guys delivered.

Unhappy - Misunderstood cruise. Thought there were music, snacks and drinks.,it was cold and seats were up On deck. This trip is for summer. We dudnmt go. Sux people scheduled. We were four and last two didn’t show. We chose not to go under circumstances.