I contacted Captain Tony for his help creating the perfect back drop for a marriage proposal. He picked us up in Annapolis and we headed out for a tour of the harbor. He had the cabin ready with champagne, flowers and candles. It didn't take me long to propose and she said "yes!". Tony then kept the romance going with... More

I chartered a boat with Captain Tony from Classic Sail Charters over the summer with my boyfriend from London. I was a first timer for sailing, and truthfully a little reticent to go on the boat. However, my boyfriend absolutely loves sailing so I gave it a shot. Not only did Captain Tony make me feel comfortable and safe as... More

Our employer awarded several of us with a sailing charter with Captain Tony as a day on the Bay....one cannot imagine how a day on the bay can feel like you've been on a real vacation, away from the hustle.bustle of the city....the silence of sailing is so relaxing and our tour included sailing under the Bay Bridge which was... More

We were looking for something new to do. So we decided to charter a half day sailing trip with two other couples and had an absolutely amazing time! Two of the people in our party were a little nervous because they had never been on a sailboat. Captain Tony made everyone feel comfortable and really went out of his way... More