Classic Sail Charters

"We had an excellent relaxing afternoon with captan Tony. The yacht was beautiful, the weather was perfect, the wind was strong and the host was warm and welcoming… we all enjoyed it! … and even got to help the captan a bit :) Highly recommend it!"

"Captain Tony was great host and helped us have a fantastic experience. He even taught my husband some sailing skills, which allowed me to relax, have some snacks and drinks. Boat was clean and very well maintained. He has a strong commitment to saftey and is very knowledgable about sailing. Highly encourage others to book a trip with him."

"Our cruise was as great as we could have hoped for. Weather forecast was not good - Captain Tony reached out ahead of time, and we were able to postpone for a day. Caught a wonderful weather window and could not have enjoyed our outing more. Our 11 year old son who was initially nervous, keeps saying he wants to go back - and so do my wife and me."

"My wife and I really enjoyed our sunset cruise with Captain Tony. We stayed at a B&B in downtown Annapolis and a Lyft got us to the marina without issue in about 10min. Captain Tony was ready to go as soon as we stepped on the dock. He's a knowledgable sailor who was willing to share his stories but also understood when my wife and I wanted time to ourselves. Can't say enough nice things about the gorgeous sail around the bay made possible by a great captain."

"We went on a sunset sail on Fathers Day and had a wonderful time. Captain Tony and crew were great company and we got such a treat of perfect weather. We were all incredibly happy with the experience and it was so easy and uncomplicated to set up. We would recommend this to anyone looking for a private charter and plan on coming back."