The wife and I chose Calypso Sailing for an anniversary outing during our stay in the Key Largo area. Calypso is geared more towards multi-day charters but they were happy to accommodate our request for an 8 hour sail. Laid back but professional is how I would describe the overall experience with Captain Lance (owner) setting the easy atmosphere. The boat was the “Blue Moon”, a Leopard 48, super clean very well appointed. Lance’s 40 years of sailing showed as he not only guided the boat with ease, his ease of managing the day made us feel that we were getting great value for our time and money. I have limited sailing experience but Lance was super willing to allow me to practice maneuvering the boat both at sail and under power. I did have to be careful with making sure to divide my time between hanging out with my wife on the bow and the hands on sailing with Lance! We moored up and did a little snorkeling, raced another sailboat and just enjoyed the day sailing peacefully to nowhere! After taking in a beautiful sunset we brought Blue Moon safely back into port. What a great day!

We took Blue Moon out for 6 days with the family, and we had a great time. Blue Moon offers a perfect lay out for a family with kids vacation, we had 4 teenagers and 2 parents. We had so much fun and the boat was in top notch condition. We cant wait to go again.

We chartered through Calypso Chaters and it was a wonderful experience. The boat was beautiful, we were able to enjoy the use of the boat as well as all that The Keys have to offer. We were able to enjoy good sailing and the boat had all the ammenities for our family. We ejjoyed beautiful sunsets. We caught fish and were able to enjoy fresh BBQ fish. Will definitely charter with Calypso again! I would give them 10 stars if I could.

The captian parked the Blue Moon directly over Christ of the Abyss and blocked the main attraction from all the other visitors. People were bumping into the boat trying to see Christ. His guests were heckled but they didnt move. Someone should talk to the July 8th captain...

We rented with Calypso sailing yesterday for my dads birthday and they upgraded us to a bigger boat the day of. The Cat was beautiful! Captain Perry was fantastic and super nice! Definitely will rent with them again!

Way too crowded. Very tiny plate of hors doeuvres. The one man band was very good and the sunset was beautiful.

Great time on the Pirates Choice Sunset Cruise. Thank you Captain Ron. Captured great photos. So relaxing.

Everything was great. Easy to work with from the first contact until departure.

Dave was awesome and so was Paul! He took our pictures and showed us how to put out the sails.They were both really friendly and very knowledgeable. It made our last honeymoon night a great experience! We will be back next time as a family and be sure to use the pirate sunset Cruise again!!Thanks guys!

We chartered Second Star with another couple and we sailed in 20+ knot winds out of Key Largo. Our boat handled the conditions flawlessly and our competent captain kept us safe. I highly recommend booking a sail with Calypso. We all loved our 8-hr sail on a luxurious catamaran!

Captain was great! So cheap for two people and four hours of sunshine on the water!! He gave us pineapple and cuties as a snack!! Amazing. Would come back and do it again.

This is a MUST DO. 6 people max. Captain dave is very entertaining. We met the most wonderful people who we will keep in touch.

Great time sailing and snorkeling. Would do it again! Worth it. Thank you Captain for a wonderful experience!

Well done boys! For the first time in my life I rode on a real steamer! :) The river around and the sea were a record of beautiful. And the captain is very cool and friendly.