Let's Go Sail The York River In Gloucester Point Virginia

The trip was very enjoyable from start to finish. Bill showed us a few pointers on how to sail (very basic, as this was our first sailing trip). Mostly we were able to just enjoy the quiet of the York River. The vessel was older but in excellent condition. You can tell he takes great pride in his craft.

What an amazing afternoon sailing! Captain Bill was awesome! Shared some history & info about the area. He allowed us to sail the boat almost the entire time. We were on the water for 2.5 hours. He took great pictures and sent them to us the next morning. Reasonably priced and definitely worth it! Highly recommend!

Delightful afternoon on the water with Captain Bill. His passion for people, sailing, history while providing an exceptional experience for each of us was refreshing. We’re so fortunate to have found his tour. Highly recommend Williamsburg Charter Sales!

I learned that sailing is beautiful, relaxing and an art. What a wonderful trip and many memories made!!! 10/10 recommend. The best part of the whole trip besides being with my son and mom.

We had a wonderful sail with Captain Bill O’Donovan on the York River. He gave each of the four members of our family a role, making everyone part of the experience, while explaining sailing, the wind, and the different points of sail along the way. What made the afternoon especially memorable was Captain Bill himself: he has a great sense of humor and is a wonderful conversationalist. We talked about everything from the Wright brothers and David McCullough to the physics shared by wings and sails, the history and geography of the York River, the U.S. Navy’s local impact, and even HMS Bounty and its famous mutiny. A beautiful, relaxing, and genuinely interesting experience. There will never be a mutiny on Captain Bill’s boat; his passengers/crew are sure to remain happy!

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 trip advisor 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 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!

It was a very relaxing, intimate and quaint environment on Bill's boat. He was very knowledgeable about the area and the associated history. He lent me a sweatshirt since I left my jacket in the car. He also found my Key West visor that I left behind and promised to mail it to me. He let several adult passengers drive the boat.

My husband and I celebrated our Wedding Anniversary by sailing (1st time ever for us) down the York River in Gloucester, Va. I got to man the helm while my Hubs sat back and enjoyed the ride. It was a great day for sailing! It was a sunny 62 degrees, light breeze (until we picked up speed! Then it was chilly!!!!) and calm waters. We are so grateful for Capt. Bill, who was so full of historical knowledge and a wonderful instructor on the how-to’s in sailing. We definitely recommend and we will be back again!!!

We had a great time, the captain was really fun. And he let my husband drive the whole time, the weather was absolutely perfect.

Bill showed our 13 year old grandson how to sail his 32 foot long sailboat and he loved it. He taught him how to set the sails for light winds and when the wind is faster. Declan was at the helm for about 20 of the 23 miles we sailed. Highly recommend.

We were the first sailing tour of the season on a brisk March day when we were visiting the Gloucester area. My husband has always wanted to sail and we wanted to learn more about the area so I found this tour thru Tripadvisor. Reading other reviews it looked a little early to go out but it was the only time that worked for us so I took a chance and reached out to see if we could arrange a tour. Bill worked around our schedule and made it happen for us. It was colder than we had figured but Bill had gloves and hats and it made for a good sailing breeze... My husband got to learn and operate the boat most of our trip, which he absolutely loved! Our teenage daughters and I enjoyed the scenery and learning about Yorktown. The starting point was easy to find, right by a really great seafood restaurant, Yrocks. This was a very laid-back, great introduction to sailing, -and very reasonably priced- which is exactly what we were looking for!

⭐⭐⭐⭐⭐ Went on Captain Bill's York River sailboat tour expecting a nice boat ride. Instead got a floating history lecture meets comedy special meets art history seminar. Honestly didn't know that was possible on a sailboat, but here we are. Captain Bill has apparently memorized every historical event that ever occurred within a 50-mile radius of the York River, and he's determined to tell you about all of them. The good news? He's actually hilarious while doing it. The man could make colonial-era tax disputes entertaining. He also whips out artwork to illustrate his points like some kind of nautical professor, which really commits to the whole "unexpectedly educational afternoon" vibe. I learned more today than I did in four years of high school history, laughed more than I expected, and didn't fall off the boat even once. Solid win all around. If you want to just sit on a boat and look at water, this isn't for you. If you want to actually enjoy yourself while accidentally becoming more cultured and informed, Captain Bill's your guy. Would recommend. Might actually remember some of this history, which is saying something.

My husband at the helm, Bill's calm confident instructions made the trip one of the delights of my life. If youre in the area take a sailing lesson or just a sailing excursion, it won't disappoint.

We had a fantastic sailing excursion today, and it was hands-down one of the highlights of our trip! Captain Bill was an absolute standout – witty, professional, and incredibly knowledgeable about Revolutionary War naval battles. He shared fascinating stories and historical insights that brought the water to life, making our sail feel like a journey back in time. The boat was spotless, the weather couldn't have been better, and Captain Bill's seamless navigation kept everything running smoothly. We even got the opportunity to watch dolphins escorting us back to the marina. Whether you're a history buff or just looking for a relaxing adventure, this is a must-do. We can't recommend it enough – book it now!

This is a good experience if you want to captain a sail boat. Otherwise, it is just a nice sail around the James River and you need to hope for good weather. The day we went out it was quite choppy, cold and windy. We were glad when it was time to return to the dock. Bill the Captain is nice and tried to make the trip fun.

I loved my first time sailing! Went with other Christian business owners while visiting Williamsburg for a work conference. Loved that Captain Bill was flexible with our wants. He even delivered us back early so we could get back in time for an evening meeting.

It was WONDERFUL. Captain Bill is so Experienced and Friendly So relaxing and Smooth Sailing The wweather was Perfect And I was deck hand :)

We got extremely lucky with a beautiful day out on the water. The captain taught us how to sail by showing us how to read winds directions and how to use nautical instruments. We will share our experience with friends and family. Thank you captain for a wonderful experience.

What a fantastic trip. Captain Bill has a well maintained and very clean boat. What an amazing adventure; so much better than any other sailing tour I've done. We deployed the sails as soon as we left the no wake zone and didn't put them away for 2 1/2 hours when we came back to dock. Yes, it helped that the weather was perfect and we had good winds. Great history of the bay that paired beautifully with our Colonial Williamsburg trip just down the road. The history lesson we asked for showed the Revolutionary War through the eyes of the bay, which most historians don't bring to life. No better way to "stand on the battlefield" than on a sailboat on the water. The captain was kind enough to let me helm the boat for the whole sailing portion and I was delighted. One of my favorite memories over 30 years ago was the quiet sound of the wind and the waves, going fast while heeling. No obnoxious motor with diesel fumes. I relived those memories and basically grinned nonstop for over two hours. Thank you, Captain, for such a wonderful birthday memory. I'm doubly amazed at the fantastic value. Private charter is absolutely the way to go. These tours make an awesome date no matter your age. Captain Bill is an ace at keeping the nautical lingo to a minimum so we could make the most of our time enjoying our trip, learning only as much about sailing as we wanted to.

Bill was incredible! My girlfriend and I cruised with Bill on a beautiful September day. Bill is so friendly, a genuine pleasure to talk with, super knowledgeable about sailing. We had such a relaxing afternoon as a couple with Bill as our captain. I highly recommend Williasmburg Charter Sails to anyone looking for a fun, relaxing, and enjoyable day on the water!

This was our 4 or 5th time sailing with Capt. Bill. It was excellent. Clean modern ship will the needed necessities. Capt. Bill was relaxed, informative and friendly. The sailing was smooth with the mainsail and jib in action. A pod of 3 porpoises joined us for the last leg of the outing. Excellent ship and skipper. I highly recommend that you sail with Williamsburh Charter Sails.

My sons and I had a GREAT time! Captain Bill was very knowledgeable and helpful in assisting us with getting sea worthy! He included us all in on the various aspects of sailing and historical information about the area we sailed in.

10/10 - Capt Bill was great! My husband and I luckily had the boat to ourselves so we had a nice relaxing sail on the water. Capt Bill gave us both a sailing and a history lesson. He was extremely knowledgeable and we felt very safe with him. BEST PART is we saw so many dolphin!! They swam by our boat and were playing in the water! Very memorable activity!

Capt. Bill was great. Although there was not much wind, it was still very enjoyable for my wife and I to celebrate our anniversary. The historical stories added to the fun.

Great experience! Part sailing lesson, part history lesson, part relaxing afternoon on the water. Captain Bill was knowledgeable, well prepared, patient, and a pleasure to spend a couple hours with. Highly recommend!

It was a wonderful time on the water. I knew my guests would find the history tour interesting, which they did. Fascinating. Afterwards, at lunch at the oyster bar, they gushed enthusiastically about you, the adventure and, especially about your smooth and thorough historical information...all without notes, they noted!! Great day, it was. And, it was fun for you to let me take the helm, an exhilarating time. Certainly will pass along the good word about your operation! Again, super time and with such a terrific host!

We had a family of four, and the experience was wonderful. Captain Bill clearly has a lot of experience and was wonderful during the whole trip. He let those of us who wanted to steer, enjoy the experience. The kids had a great time, and the York river is really peaceful and not crowded. Highly recommend, and thanks Captain Bill for a great day on the water!

We had a nice calm sailboat trip. Not much wind but the Captain knew how to find it! Traveled out by Coleman Bridge. Got to watch a bridge opening for a Navy ship to pass through.

We had a wonderful time sailing with Captain Bill on his beautiful boat!! The weather was amazing allowing us to enjoy with the sails and historical scenery!

We had a wonderful time sailing with Captain Bill on his beautiful boat!! The weather was amazing allowing us to enjoy with the sails and historical scenery!

Beautiful day and great fun! We enjoyed our cruise and meeting new people. Captain Bill was knowledgeable and fun.

Booked this trip as a birthday outing for our 17yo nephew and he loved it. Captain Bill was a great host, teaching us about sailing in general, the York River and the Chesapeake Bay. He also took great pictures and had them to us early the next morning. We happened to book for a particularly hot day and Bill adjusted our departure time to insure the best weather for both our comfort and sailing. As a tourist returning to the area where I grew up, I think I've done everything there is to do and sailing the York has to be in my top 3 activities.

This was such a fun day. We went on the lesson cruise where we got to steer the boat. Captain Bill was amazing captain and host. There were only 6 of us so we all got plenty of time at the helm. I highly recommend this sailing cruise.

We couldn’t have asked for a better day on the water. Captain Bill was incredibly informative sharing the history of the Yorktown battles in the Bay and on land. In addition we learned a tremendous amount about sailing.

We had a wonderful time on the water! Bill the captain was a delight and very knowledgeable. A great teacher and guide. Suitable for any small group.