Well, we got on this ship for one reason... The sunset. Even though we got an amazing sunset, we got so much more! Captain Rio and the two gorgeous women with him made the sailing both fun and pleasant ;-) Would recommend taking a sail with this ship any day!

Went out for 2 hours in the afternoon. Crew consisted of Rio (he's the captain) and his two hands, Jenn & Margo. All three of them did a great job sharing history, both of Key West as well as of sailing. Didn't see any dolphins or turtles, although the crew had said there's only about a 40% chance of seeing... More

Great boat to sail on and the most knowledgable crew. We took advantage of the frequent sailor card and went 3 times in one week. All the sails were great and especially when the wind was up and the boat flew along. The fist sunset we saw was by far one of the best we had seen in Key West... More

Very enthusiastic crew (surprisingly so, considering they do this everyday). We had a great time and they helped us utilize every photo opportunity we could. And then there was the hot captain. Maybe I've been drinking, but Rio was just plain adorable :). Great trip, overall.

We had a fantastic trip on the Jolly Rover II. 1st, there was a nice wind for our sunset cruise, Capt Rio said we hit 10 knots! So we did some nice sailing, then brought the sheets down to participate in the "Bloody Battle" of the Conch Republic anniversary week. So much fun! And the fact that you can BYOB... More

We did a sunset cruise and because the trip had only 10 participants we got to know the crew and the other passengers. The ship was very clean and the crew very friendly. We got to gelp setting the sails and stearing the ship. When you are in Key West, take a cruise on the Red Sail Jolly Rover.

My friends and I sailed with Captain Rio twice this week as we celebrated my 50th birthday in Key West. The afternoon sail was great - we were able to help rig the sails, and felt very comfortable on the boat. Winds were not strong, so we motored a bit, and were thrilled to have several dolphin swim around the... More

We loved our sunset sail. There were four of us and we packed a wine and cheese picnic, which was great to bring on board while enjoying the most amazing views. The crew - captain Rio, Margo, and Mindy were the best. So knowledgable, friendly, and did everything to make the best of our sail. Highly recommend.

Fun sail, knowledgable crew. Well organized and the crew is great fun:) Beautiful boat. Quiet ride, nice views. Goes out further than the typical "party boat".