Gloucester Point Small-Group Sailing Lesson

Summary: Great experience! Bill was welcoming and very knowledgeable. He taught us a lot about sailing, the area, and revolutionary war history. My son really enjoyed helping sail the boat. Would definitely recommend!

Summary: Such a fantastic experience, we booked an exclusive trip and it was so fun. Getting to drive the boat and learning how to handle it made the trip. Capt Bill is a fantastic teacher. 10/10 would recommend!

Summary: What an amazing experience!! Never been sailing before so didn't know what to expect. Definitely a.thrill ride!! We had a perfect day with the perfect wind and a perfect Capt to make this experience such an epic time!! Will definitely be back again soon. I'm addicted!!!

Summary: My husband and I went sailing for the very first time, and we had an absolutely wonderful experience! Captain Bill was fantastic—friendly, knowledgeable, and made us feel comfortable from the moment we stepped on board. He made the trip relaxing, fun, and unforgettable. We couldn’t have asked for a better first sailing adventure. If you’re thinking about going sailing, we highly recommend Captain Bill. Thank you for an amazing experience—we’ll definitely be back!

Summary: Captain was very professional. Very good experience.

Summary: If you've never been sailing before, this experience is absolutely worth it. My wife and I went for the first time this weekend, and we had an amazing time. Captain Bill is an experienced sailor who clearly knows his craft. Even before you step aboard, he does an excellent job communicating. He keeps you informed about the weather, any schedule changes, where to park, restaurant recommendations, and just about anything else you might want to know before your trip. Once you're on the boat, Captain Bill is friendly, patient, and an outstanding teacher. He shares fascinating history about the Yorktown area and explains the fundamentals of sailing in a way that's easy for complete beginners to understand. We sailed on what I believe was a 36-foot sailboat, which comfortably accommodated our group of six during the two-hour adventure. We arrived about 15 minutes early, and there was plenty of parking for the 11:00 a.m. sail (I can't speak for the afternoon trips). The route takes you into the Yorktown channel, where Captain Bill gives everyone the opportunity to experience several sailing maneuvers and really get a feel for how sailing works. You can even take the helm, help trim the sails, or simply sit back, relax, and enjoy the ride—it's entirely up to you. My wife and I thoroughly enjoyed this adventure. Whether you're looking to learn the basics of sailing or simply spend a relaxing couple of hours on the water, I highly recommend sailing with Captain Bill.

Summary: We had a fantastic time sailing with Bill. We learned a lot about sailing and the area.

Summary: We had an amazing day sailing with Capt. Bill. His knowledge, professionalism, and dedication to seamanship is impressive. The Deadline (name of sailboat) was ship shape, extremely well maintained and smooth on the water. The weather was perfect. The experience we had will last a lifetime time. Go sail with Capt. Bill!!

Summary: Capt. Bill was an excellent host and captain. No nonsense, but very pleasant, knowledgeable, and accommodating. Desired for his guests to have a good and safe experience. Provided good revolutionary war info about the area. Weather conditions where excellent for a very nice sailing experience. We highly recommend this cruise.

Summary: From the moment I first reached out to book, Captain Bill was incredible. He made everything so easy with prompt communication and answered every question. By the time we arrived, we already knew we were in great hands. The sailboat was the ideal size for our family of five. It was spacious, comfortable, and the perfect setting for an unforgettable afternoon on the York River. We spent the day sailing with great music playing, taking in the beautiful views, and listening to Captain Bill share the history of Yorktown in such an engaging and fun way. You could tell how much he loves what he does, and that made the experience even more special. My sister and brother-in-law were visiting from out of town, and I truly can't imagine a better way for our family to spend the day together. We even got the chance to take the helm, which was definitely one of the highlights of the trip. If you're visiting Williamsburg or Yorktown, or even if you're a local looking for something special, do yourself a favor and book a sail with Williamsburg Charter Sails. It was one of the highlights of our weekend, and we'll absolutely be back! Thank you, Captain Bill, for giving our family such a perfect day on the water!