The Jolly Rover caught my eye during a previous visit to Key West and I wasn't leaving this time without a sunset cruise on the Schooner! Online booking was easy and check-in was a breeze. The staff and crew were great and provided a wonderful sail. They even "fired" the cannons at the other schooners on the water which was... More

The boat was very clean, with plenty of seating. Crew and the captain were very helpful with anything you may have needed and they were also very friendly and informative about Key West and the water. The weather in this day was overcast with very little wind, but the trip was relaxing.

The boat was great, the crew was fantastic and the whole experience was unforgettable. If you were going to spend money in Key West on one thing other than drinks this should be it!

My husband and I took the sunset trip on May 13. Despite the sun hiding behind some low clouds, the sailing was awesome and the trigger-happy crew made it an unforgettable experience ;-)) I warmly recommend this trip that suits young and old alike!

My Husband and I were visiting the Florida keys for the first time and decided we would like to try some sailing. We found the Jolly II Rover while walking along the harbor in Key West. We booked a sunset tour for that evening. It was fabulous!! We have been sailing before on small boats and catamarans but this was... More

Staff was friendly and approachable. Learned so much, they are not afraid to answer questions :)

While in Key West for the weekend we took a sunset cruise on the Jolly II Rover and my wife and I had a great time. Did not get to see a sunset because of cloud cover but still felt it was very well worth the time and cost. The crew was a lot of fun and made it enjoyable... More

A really great time! Competitive pricing and the best experience ever. Much better than a Sebago or Fury sunset cruise. Bring some key lime pie and drinks and you will really make a ngiht of it!

What a great time!! We had such a great time with the sunset cruise we decided to do the Wrecker's Race with them!! The whole crew was awesome!! Captain Rio allowed us to steer and also help with the sails. Brenton (hopefully spelling is correct) and Andrew and Jen were so nice!! I would recommend the Jolly Rover to everyone... More