15 Best Key West Sailing & Catamaran Tours

“What a wonderful experience and the best way to see the sunset. The crew was extremely attentive and very friendly. Enjoyed getting to hear about their backgrounds, diverse as they are. Well worth the cost!!!”

“Quality sail on schooner with wine tasting and small plates. Paired well with fun staff. 5 stars all the way.”

“Very relaxing and enjoyable sailboat trip with the captain and his first mate. They were attentive and talkative and friendly and very helpful. They did everything they possibly could to make sure this was a great trip. We only had six people on the boat…”

“Skies were a bit cloudy, but Capt Janet and crew sail the ship to the best sunset viewing spot as possible. Even had a few dolphins off the bow. What I enjoyed the most was the interaction with the crew ex: asking for volunteers to…”

“Great seeing the dolphins in their natural habitat. The boat crew were great and no point we didn't feel unsafe.”

“It rained so we were upgraded for free. Cruise was fun, music was great! Open bar and appetizers were a nice touch.”

“The snorkel tour was such a blast from start to finish. The crew, Captain Chuck and Jared, had the perfect mix of fun energy and professionalism—they made everyone feel relaxed and ready to jump in. The water was crystal clear, the reefs were gorgeous, and…”

“Even though it wasn't a perfect weather day, Theresa and Liz provided us with a great time! Saw sea turtles, lobsters and lots of dolphins.”

“snorkeling was wonderful It was very hot so the water was amazing. Dry Tortegas was ok. Something I would only want to do once.”

“Had an amazing experience, very friendly staff. This is was our first time and the staff explained the process very clearly.”

“The crew was very helpful, especially to those who were not experienced. They were focused on safety and also making sure everyone had a good time.. The snorkeling was good and was able to see a variety of fish and also the colors of the…”

“The Captain and crew did a great job. We had a perfect sail, and the overall experience exceeded expectations. The appetizers and drinks were just right. We highly recommend taking this trip.”

“The Sunset sip and sail was awesome! They had an open bar and free appetizers available to snack on, and an option to upgrade to a full dinner for a small additional cost. But let's face it, you book this for the experience of sailing…”

“We had a great time on the boat. Would recommend to anyone that is either in Key West for the first time or is a regular visitor.”

“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…”