Top Virginia Sailing Trips

Serene day on the water. Captain Tom was an excellent teacher. Very knowledgeable on sailing. He was delightful and easy conversation. Will definitely go again when in the area.

The best experience with Captain Bill. You can tell his sailing experience is deep, and he is so patient and knowledgeable. Great conversation with others on trip. We just needed a few quiet hours of water and wind therapy, and he delivered.

My six year old grandson and I had a fabulous sail today with Capt. Bill. We have loved being on the water for many years and this was no disappointment. It was a beautiful day and the water was great. The six year old loved it and enjoyed being the “Captain”. He did a good job and Bill was so kind and helpful. We both had a great sail and I will be back with other family and our other grandson. This is a must do if you enjoy time on the water.

Excellent sailing. Our captain Bill was wonderful. I would have liked to know where to meet Bill beforehand. Other than that it was wonderful. I would recommended to anyone.

Had a wonderful time, Captain Bill was great

Had a great time with Capt Bill! He kept us apprised of the conditions a few days in advance which was nice as we had to travel 2 hrs to get there. It’s a cozy sail with a few folks, we had a blast with a family from Nebraska with roots to Kansas City, same as us! It’s was a partly cloudy day and we just sailed around and relaxed. We did enjoy the cafe and grill on site at the marina.. great food and service. We went on a Tuesday and did the 11 AM tour.

This was one of the best experiences I have booked through Cool Destinations and at a very reasonable price. Captain was knowledgeable and allowed guests to have a hands on experience if they chose to do so. We were fortunate to have excellent conditions the day we went. Highly recommend. The restaurant at the marina is also worth grabbing lunch at after.

We had a great experience with Captain Bill. He was very knowledgeable and a great teacher/communicator. It was a hands on experience for a few of us, which was an added perk.I would definitely trust Capt. Bill to cross the Potomac River any day of the week.

The yatching experience was amazing. I would go on it again my family. Although I have to practice multiple times to sail the boat better.

Took our grandson for a first time experience for all of us. What a wonderful way to spend the day. Captain Bill was booked for the day but made sure we could enjoy the day making accommodations for us to go out with Captain Bob. We all enjoyed our day immensely would highly recommend for anyone interested in sailboating will go back. Thank you!!!!!

Phenomenal Father’s Day sail with Capt Bill! Very peaceful, laid back afternoon on the York River. My husband has been interested in sailing and he absolutely loved it! Bill is so informative with years of experience and let hubby sail! Memorable trip!

We requested 4 double rooms, we received 4 times 2 separate beds! You talk about the sandy beach, the concept of beach needs to be reconsidered; stones, pebbles, no way to walk along the beach. You must clear 4 meters of cobblestone, large irregular stones, before having a bit of sand in the water. False advertising because we wanted a sandy beach; there is a concrete promontory where lounge chairs are set up, large sand, you had to have special shoes to walk or go into the water, it was difficult even to keep your balance when entering and exiting the water, risk of injury!!!! No fresh fruit juice, you had to pay for fresh orange juice!!!! and then you mention that there is a road, clearly specifying that it is not a low-traffic road but almost a highway, with motorcycles, cars, buses, a deafening noise whether you are at the hotel, in the restaurant, or on the beach. It's a shame because it's a beautiful hotel, with pleasant and helpful staff. A lovely discovery, the squirrels. Very good and varied meals. The hotel is clean, but you need to be more honest when selling a stay with no sandy beach! A road that makes a deafening noise! Paid orange juice! I also have videos showing that we lose our balance when entering and exiting the water! Impossible to walk along the beach!

We enjoyed a delightful day sailing with Captain Bill from Williamsburg Charter Sails. Bill was absolutely wonderful with our group of 11 high school boys - most of whom had never been on a sailboat. This turned out to be an experience of a lifetime for many of the boys. Bill was patient and knowledgeable. He gave a clear, easy to understand introduction to sailing - and also - found time to share stories and tidbits of local history and to point out the interesting landmarks we were passing. We also saw pelican, osprey, and other sea birds. Later, we came across Naval Academy training activities and saw a hovercraft taking off. Our students loved the whole trip and continued to discuss the experience through lunch. And then, to top things off, Captain Bill snapped a bunch of photos and sent some beautiful images to us the very next day! The guys loved that too. We highly recommend Williamsburg Charter Sails and would love to find a time to get back on the water with Captain Bill.

We had an amazing time with Captain Bill sailing on the York River. The weather helped immensely (it was a beautiful day), but the experience - especially for our twin 8yo - was exactly what we had hoped for. While this isn't a "kids" sailing experience, Capt Bill did a wonderful job of explaining the details of sailing in an approachable way that kept both of our kids engaged. The boat was beautifully kept, the boarding and setup was simple and carefree, and all we had to do was enjoy the wind, the sun, and the voyage.

My wife and I had a wonderful day with Captain selling on the Yorktown River hearing about the history and battles that occurred there.

It was a beautiful day to be on the water. Bill shared historical highlights of the area and provided opportunities to learn a little bit about sailing. I would highly recommend this excursion!