Absolutely worth it! The captain and crew were really great, and the owner was on board too! I even got to sail the ship (and yes, we actually sail - not the power sailing the catamarans do). The crew likes to fire a small canon at passing ships which makes it even more fun. This is not a booze cruise! If you want to get drunk, go somewhere else. They have water and snacks available and a cooler if you want to bring your own drinks. I would definitely do this again in a heartbeat!

The sunset sail was fabulous! We had considered other cruises, some of which included food, drinks and music. Out on the water, we were glad that we were not on the noisy boats which we passed in the harbor. The BYOB insured that we had our drinks of choice. The small number of passengers allowed the excellent crew to mingle, as well as be attentive to the guests. The owner was on board, as well, and obviously takes pride in his ship. The ship was clean and well cared for, and the crew experienced. Highly recommend!

A gracious and welcoming crew, great sailing, and an uncrowded but fun cruise made for a great evening in Key West! BYOB drinks worked out perfectly in the provided cooler. Lots of photo opps and of course cannon fire (!) -we will return!

Fun sunset sail! We had a wonderful time (family of 4 with two young adult children) on this beautiful two mast topsail schooner for a sunset sail. Friendly and capable captain and crew, and the owner was also on board and told us some great stories. We went under sail and really experienced the sea. For fun the schooners would shoot at each other with their cannons, and our son was able to take the helm for a while. We saw a beautiful sunset with an unobstructed view. It was nice to be able to bring our own drinks and snacks, and they provided a cooler and bottled water. We definitely would go on this sunset sail again if we return to Key West.

The captain and crew were first rate. Lots of commentary, humor and stories. The trip was very much smooth sailing. Finding the ship and boarding were easy with a parking lot at the dock. I've been on several sailing excursions and I think this crew did the best with the sails and looking after guests. The sunset was very good. We left having enjoyed all of the trip. Highly recommend this.

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.

It was a magical night on the ocean. The wind was light, dolphins were about, the sunset was gorgeous. Elijah, Gracie and Drew were easy going, informative and hard working. The Jolly Roger is a great sunset cruise.

Definitely recommend! The ship is so beautiful and the experience is unique! My parents and I have been on many boat rides but to be on a ship and actually sail without a motor for some time was an unforgettable experience! The ship was also in tip top shape! I was also given the opportunity to pull on the ropes that brought one of the sails up and my parents and I had our pic taken behind the “wheel.” The crew really went out of their way to make sure you’re having an enjoyable time. Bill, the ship’s owner, talked to us for a long time during the trip. Very nice humble man who takes pride in his ship. Kudos to also Drew, who was so pleasant to talk to on the phone when booking our tickets. Chris, who steered the ship, was so sweet along with Chase, who also worked on the ship. They fired a small canon after the sun went down. It was so cool!!!! Best place to see a sunrise in Key West aboard an original ship, not in a loud boat with many people drinking. We were able to bring our own food on board and were provided chips. Please come out and support this small business. There is one major company that monopolizes on most of the tours out in Key West shutting out the small businesses. Thank you and you won’t regret it! One of the highlights of our trip to Key West! ❤️❤️❤️

This was an amazing and unforgettable experience. Captian Elijah and crew Chase and Drew were very informative, funny, personable, and shared their passion for sailing. We saw dolphins, an amazing sunset, cannon firing on other boats, history of the keys and boats, and so much more. It was family friendly and we even got to steer the schooner. You can also BYOB. Captian Dan who checked us in was also very friendly and spoke with our 12 year old daughter getting her pumped up for the sail. Earlier in the day we did a cataraman sail with Fury (another company) and were so disappointed. The crew there was not friendly and we didn't see them smile once. Please save your money and do this sail instead, it was completely the opposite. We wish we had done this sail earlier in our trip to the Keys so we could do it again while we are here but we are leaving soon. They have discounts for your second sail and the third is FREE. We will definitely be doing it again next time we are in the Keys! Enjoy your honeymoon Elijah!

Captain Elijah is the best! What a great evening! The atmosphere of the schooner, the intimacy of a smaller number of passenger’s, the interaction of the crew with us was fantastic. Pass on the big party boat sunset cruises and book you evening on the Jolly II … you will be thankful you made the choice.

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.

We sailed on April 18,2023. Our captain Elijah and crew Drew and Chase were great. They took great care of us and all of the passengers. It was a great evening for watching the sunset and the captain made sure the ship was in position for watching the sun go down. My wife even got to steer the ship for a bit. Maybe a few more canon shots would be cool. "Sail on Captain Ron" Bob & Beth Randall

We had a great time on the jolly rover, there was 6 of us friends all had a great time, the crew was very friendly and knowledgeable made it great for us, it was our second time on the boat and will go again next time in keywest, and yes they do really light of cannons. Anna

The crew on Jolly Rover 2 was entertaining and informative, and really put on a show for us throughout our day sail. Having the beautiful red sails hoisted and riding through the Key West breeze was just what we needed to truly relax. Thanks!!!!!! Wish this trip was a Never-ender!

This was totally different from the previous boat rides/tours we'd been on...no dolphins or sunsets but a part of an actual race. I don't know how many of the other boats take on passengers during a race event. That being said I do think the America II had extra people on board but that boat is in a class of its own and specifically built for speed. The owner, captain and crew were outstanding....the only downside was the waves out there were pretty good ones today and I don't think anyone left the boat totally dry. It was a cool experience 😎