Williamsburg Charter Sails — Local services in Gloucester Point

Capt. Bill showed our group a wonderful river cruise experience. Our crew was mostly novices with two experienced members who had not sailed in over 20 years. The conditions were perfect and we now have a lifetime of memories. His boat is very clean and stable. His equipment is excellently maintained. We cruised out to where the mouth of the York River meets the Chesapeake Bay and back with favorable seas. The good Captain turned over the helm as soon as we raised the sails and gave us guidance as needed to pilot the boat. We even had the opportunity to raise the spinnaker on the way home. What a treat.

He was very knowledgeable on the history of the region and points of interest that were dotted along the shoreline.

As we were returning, the fairer members of the crew were a little disappointed that they had not seen any dolphins. Before too long one of the crew spotted fins about a half mile from our position and Captain Bill directed the helms woman to set our course in their direction.

Within minutes the 20 plus dolphins put on a show in their natural environment that would make any Sea World show seem pale. Swimming all around the boat and breaching up to two at a time, the oohs and aahs were none stop for about 15 minutes. What an incredible way to enter the harbor. Captain Bill’s rates are well below market in the charter community with outstanding value. I give critical and objective reviews. This assessment is not inflated, just as we experienced it. This is one opportunity you should not let go by. ...

There's a reason Williamsburg Charter Sails is the #1 tour in Williamsburg. It's because of owner and captain, Bill O'Donovan. From the moment my wife and I met Bill at the marina, he made us feel welcome. He is very personable and it's immediately obvious he's all about safety on board.

His 32' Hunter sailboat, Deadline, was pristine and looked brand new. As soon as we were underway, it was obvious he is a very experienced sailor (he holds a 50 ton captain's license earned after many years on the water). If you're interested in sailing and/or obtaining your own captain's license, Bill will gladly discuss the process.

The 3 hour cruise up, down and across the York River was a blast. Not only do you gain a lot of knowledge about sailing, you get a history lesson as well. The Williamsburg area as a lot of history, as most people are aware, and Bill shows not only his passion for sailing, but for American history as well. You will learn a lot and have fun at the same time. Bill even let me sail the boat for a good portion of the trip and my wife even got in on the action.

As a bonus, we saw a pod of dolphins in front of the boat as we were coming back in - so awesome. You couldn't peel the smiles off of our faces. All in all it was a great experience. If you love the water like we do, we highly recommended taking this tour with Captain Bill. Easily the highlight of our 4 days in...

Sailing with Bill is absolutely perfect! Our family enjoyed a private 3 hour sail on a Saturday when afternoon showers were in the forecast. Bill was incredibly flexible and accommodating; he worked around both our schedule and the weather to get us out on the water ahead of the storms.

The sail itself was serene and wonderful. My oldest daughter and I even took turns at the helm. She kept the wind steady in the sails, while I managed a top speed of 11.7 mph! It was a fun and memorable experience for both of us. My wife and younger daughter just relaxed and enjoyed the experience for the peace, quiet, and beauty of nature.

Bill is not only a skilled captain but also a wealth of knowledge. He shared fascinating insights about the Yorktown battlefield, the battle of the capes, and the Chesapeake Bay Estuary, making the trip both relaxing and educational.

The price for this private cruise was extremely reasonable, especially when compared to other local sailing options. While other charters were slightly cheaper, they came with crowded boats. With Bill, it was just our family and the open water; peaceful, personal, and unforgettable.

We highly recommend if you're looking for an intimate and enriching sailing experience in the Yorktown area! It was the perfect finish to our week in the historic...