Classic Sail Charters

This was absolutely amazing! We rented the boat when my in-​laws came to visit and couldn’t have asked for a better experience. Suzy was great. I highly recommend-​worth every penny!

We had a great sail with Capt. Suzy and Co-​Capt. Miguel. Suzy was wonderful and even let my father steer the boat the whole cruise. Morning sail so there was coffee and a wonderful strawberry cake waiting for us. Capt. Suzy will adjust your sail to your liking, nice and smooth or high adventure. This was a family adventure, however I would definitely schedule a sunset sail with my husband.
Highly recommend Classic Sail Charters.

I arranged an evening cruise with Tony on a Saturday and informed him that I would be proposing to my girlfriend (now fiancé). This was something he had been through before and had everything needed to make it an unforgettable day. Tony had a great camera that took amazing pictures of the entire proposal, he had a bottle of champagne on ice waiting for us after she said «yes», and he gave us privacy on the front of the boat to enjoy the weather and the special day. He was the ultimate host, having a spread of pretzels, crackers, cheese, wine, etc. Tony knows the surrounding area very well and was able to inform us throughout the trip of the various history Annapolis has to offer. Everything went perfect and my fiancé and me will never forget the experience we had sailing with Tony and getting engaged on his boat. I highly recommend him for anyone looking for a private, yet friendly time on the Chesapeake!

In looking to do something unique as part of my proposal to my now fiancé, I booked a sunset cruise with Captain Tony, and I couldn’t have been more pleased! Captain Tony is an excellent sailor and a complete gentleman. He worked with me to set the view up perfectly for a sunset proposal, brought out champagne for us to toast on the bow, and even took some great pictures!
Whether looking for a romantic sunset cruise, or taking friends and family out on the water in Annapolis, Captain Tony is your man!

As a part of his proposal, my fiancé recently chartered a sunset cruise on Classic Sail Charters for us and 4 close friends. Captain Tony took us out for a 2.5 hour sunset cruise. The boat was stocked with beer/​wine and snacks. Captain Tony did an excellent job facilitating the proposal by acting as if it was one of the other passengers ideas, including the dockside greeting. After taking us on a full sail leg out towards the bay bridge, we returned up the Severn River with beautiful views of Annapolis Harbor and the Naval Academy. When we reach calm waters, he set up seats on the bow for us to relax, providing the perfect setting and timing for a proposal at sunset.

My husband and I had some friends in from out of town, and wanted to give them a true Annapolis experience. Booking a private sail with Captain Tony was just that and more. Captain Tony is so friendly, knowledgeable and experienced. He put us at ease and made us feel right at home on his beautiful boat! He also provided us with tasty beverages and horsdeurves to enjoy as we sailed the bay and enjoyed the sunset. We all thoroughly enjoyed ourselves, and my husband and I have already booked a second excursion with him! This is truly an awesome experience for locals and tourists alike!

Sailing with Captain Tony is wonderful! He’s a great host, his boat is beautiful and plenty big to accommodate our group of five (or more). He’s easy to get along with, fun and we had a blast sailing with him. It was like sailing with an old friend. Would charter with him again in a heartbeat.

Tony is great, both as a sailor and a gentleman. His low-​key approach combined with his gentle sense of humor made our sunset cruise very relaxing and enjoyable. My wife and our four daughters can’t wait to go sailing again with Captain Tony.