Let's Go Sail Virginia

Captain Bill was so very pleasant and knowledgeable. We had such a wonderful time and would highly recommend taking a sail with him to anyone interested in something non conventional as a date idea. It was our anniversary and Captain Bill showed us an beautiful afternoon.

Best sailing adventure around! Capt Bill is the greatest. Great trip for relaxing, learning, and being on the water. Capt. Bill kept the conversation going when needed and the let the music keep the vibe when needed. Highly recommend!!

Captain Bill was great! He even let us drive the boat, it was amazing.

Great experience! We chose the History Cruise and Captain Bill was excellent- extremely knowledgeable of the events that took place in Yorktown during the Revolutionary War, delivered with a bit of humor. The boat was beautiful and Bill is obviously a very accomplished sailor. Would recommend this excursion to anyone. Ray Charles

Outstanding sailing experience! Have done similar cruises in many other locations and this was the finest by far. Captain Bill was a knowledgeable and gracious host. Good instruction for the guests at the helm. Clean, well maintained boat helped make the cruise even better.

My family and I had a wonderful time sailing with Captain Bill. I would recommend this adventure to everyone.

My friend, Kim, and I had a fantastic time sailing with Captain Bill. We were lucky enough to experience a very blustery day, so the sailing was fun, fast and a great workout. Captain Bill was very knowledgeable about the area and imparted some great historical tidbits, which we loved. I hadn’t sailed in quite some time, so he was very helpful in describing the different sailing approaches and tactics. We would definitely charter with Williamsburg Charter Sails again.

The speed was slower than I expected but very enjoyable and relaxing sail. We learned a lot of history and the paintings made it come to life. I was able to steer the sailboat and was assigned the bowman at launch/return..

Always an amazing time sailing with Capt. Bill. My best friend and I brought lunch on board and it was a beautiful sailing experience. Will book again and again. Highly recommend.

What an absolutely wonderful experience! My husband and I celebrated our anniversary with a private sailboat/yacht charter with Captain Bill and it was such a special and memorable part of our trip. There is something truly special about being out on the water, enjoying the beautiful scenery, peaceful surroundings, and the opportunity to simply relax and enjoy time together. Captain Bill is knowledgeable, personable, and patient, even giving us the opportunity to take the wheel! We learned so much from him along the way! Our private sailing adventure was the perfect way to celebrate our anniversary and create another wonderful memory together. We highly recommend Captain Bill O. to anyone looking for a relaxing, personal, and unforgettable sailing experience. We would absolutely sail with him again! Thanks Captain Bill!!! A wonderful captain and a five-star experience!

Invigorating, relaxing, and fun adventure! DO NOT miss this!!. Capt. Bill’s knowledge and passion for sailing and these waters is contagious. He enjoys teaching and trusting all interested to a level where you are actually sailing! It is incredible! He is kind, patient, and interesting, allowing each guest to experience his beautiful boat how they want to spend their time. Thank you for a fabulous day!!!

We really enjoyed the sailing. Highly recommend.

Enjoyable day on the water. Good wind for sailing. Captain was an excellent storyteller. I learned so much about the Revolutionary War & the waterways. Despite my fear, the captain beguiled me into taking the helm And I am glad he did.

My husband and I had a wonderful time sailing with Captain Bill. I got to sail the boat for quite a while on my own which was so fun! We relaxed and enjoyed the views on the York River. The price was super reasonable compared to the many other boat cruises we have been on around the US. We felt very safe and would gladly go again.

This was a great experience! Captain Bill made it extra special with his history knowledge and narratives. He provided us with pictures after the sailing. It was a truly serene sailing on the York River!

Fantastic!! Was just 2 of us, and Captain Bill let me at the helm most of the trip. Was definitely the highlight of my vacation. Would highly recommend very relaxing felt totally safe, and learned great facts and stories about the area! A total MUST if you visit the area.

This day was amazing. Not only did we get to hear the history part we also got to sail the boat. The icing on the cake for me was seeing the dolphins come so closely to the boat. This was an awesome experience with Williamsburg Charter sails. I highly recommend booking a sailing trip. It was a wonderful add to our honeymoon. Scheduling was easy and he was responsive and detailed.

My husband and I had a great time with Captain Bill on a beautiful afternoon of sailing. After devoting ourselves to seeing historical sites, it was so nice just to kick back and enjoy an afternoon on the water. Couldn't have been better; we got to see several dolphins close up as well--one came up right behind the boat!

Captain Bill was very knowledgeable in history. Truly enjoyed the experience. Was able to manage sailing with his expertise. Coming from the desert, this was once in a lifetime for us. thanks again, Captain Bill.

Capt Bill taught us a lot about sailing which was our purpose for the trip. He let us help with the sails and steer the boat the entire time. Since we are interested in learning to sail on our own, he answered all of our questions and followed through with information to get us started. Such an enjoyable day on the York River!

Captain Bill gave everyone the opportunity to take the wheel. We loved enticing about the whole trip!

What an absolutely wonderful experience from start to finish! Our river cruise with Capt. Bill was the highlight of our trip, and we can't recommend it highly enough. Capt. Bill himself is a treasure — gregarious, sociable, and full of great stories, he made everyone feel welcome right away. At the same time, he inspired a strong sense of safety and confidence, so we could simply relax and enjoy the ride. And speaking of the ride — we actually got to steer the boat! That was such a fun, hands-on touch that made the experience feel truly special. The scenery was beautiful, and we were thrilled to spot dolphins along the way — a memory we'll cherish. The water was so tranquil and peaceful; it honestly made us feel great just being out there. Part of what made the day so memorable was the company. We met the loveliest fellow passengers — Deb and Mike from N. Dakota, and Sheila and Dave from Utah. Everyone was such good company, and by the end of the cruise it felt like we were all old friends. As if that weren't enough, we even got a discount to the seafood restaurant on the pier, where the food was absolutely delicious — the perfect ending to a perfect day. If you're considering a river cruise, look no further. Capt. Bill delivers an experience that's fun, relaxing, and full of personal touches. Five stars, without a doubt — we'll be back!

Great time on the water. We were with 5 other very friendly people who made our trip fun. Captain Bill was awesome!

This was our second adventure cruise with Captain Bill and we couldn’t be happier with the experience. Captain Bill is very knowledgeable about sailing and our local history. We had fun learning about both each time we sailed with him. It was also nice to have a private setting with our family, who joined us from out of town. If you want a relaxing and FUN time out on a boat at a very reasonable price, book with “Let’s Go Sail Virginia”. We’ll definitely be going back!!

Great sailing experience and one of the nicest days on the water! Our ride was awesome from start to finish! We were lucky enough to catch some wind and Capt. Bill was amazing! He showed us historical locations, gave us a sailing lesson and managed to find us a school of dolphins that circled the boat! Could not be any better of a trip! Thank you Capt. Bill!

Captain Bill was amazing! He showed my husband how to sail the boat, told great historical stories, and was very knowledgeable. My hat fell overboard and he made every effort to save it. He successfully saved it! We loved the boat ride and would love to go again!

We had an amazing experience sailing with Capital Bill! The boat was beautiful, the views were breathtaking, and the entire experience was relaxing and enjoyable. The captain and crew were friendly, professional, and made us feel comfortable throughout the trip. It was the perfect experience for a couple looking to relax, enjoy the water, and spend quality time together. We especially loved the peaceful atmosphere and beautiful scenery. I highly recommend Capital Bill for anyone looking for a fun, relaxing, and memorable sailing experience. We would definitely do it again!

We had a great time with Captain Bill. We especially appreciated his flexibility with - and being well prepared for - the weather. Would definitely recommend.

Bill was tremendous, patient and friendly throughout our cruise. It’s all worth it. I plan to take my international students on this cruise

Nice experience out on the water. Highly recommend it. Bill was very attentive to all on board. Nice tidbits of info also

Captain Bill was very knowledgeable on sailing. He provided us with written information and pictures of our adventure. Highly recommend!

Captain Bill took us out on the York river on his beautiful sailboat. He was very patient with my kids and let them steer the boat for a while. We were also able to go swimming - would definitely go again!

We found Cap't Bill and could not have been happier with the price and experience. We initially ran into trouble arriving on time to the marina due to the draw bridge holding us up on the other side of the York...but the Cap't was already aware that there would be that issue after realizing the Navy was coming down the river at that time. He delayed departure while we made our way to the dock to set sail. During the 2.5hrs we sailed, each of our family took the con, 'jibbed the sails, picked up an understanding of how the vessel is pulled through the water instead of being pushed, and shared sea stories. How can you ask for more?

The sailing was a wonderful experience. We went with 4 children ages 4, 9, 12, and 14. It was a bit too long and hard to remain seated for our 4 and 9 year old. Our 12 and 14 year olds really enjoyed. We spotted 2-3 dolphins in the distance which was a highlight and the kids got turns at sailing.

We had a wonderful sailing experience! The captain was friendly, personable, and knowledgeable about the area. He made the trip especially memorable for my dad by letting him take the helm for most of the sail for the first time in almost 30 years - an experience he absolutely loved! The boat was clean and comfortable, and the quiet background music created the perfect atmosphere without being distracting. Communication before and after the trip was also excellent. I highly recommend this sailing expedition to anyone looking for a relaxing, enjoyable, and memorable experience!

Thank you Captain Bill! You were awesome! I had a blast in the past! I can’t wait to have more adventures in the near future!

We had a group that exceeded the max of 6 but Captain Bill worked with us to have 2 sailboats out to the river at the same time for a private daytime sail with our family. While we were not on the same boat. We shared the same area and we were able to interact while sailing. It was a fantastic experience for us to learn to sail AND learn the history at the same time. We also appreciated the peace and quiet of the ocean - Captain Bill said, no cars honking. The wind and air was fresh! We can’t wait to go back again!

This was a absolute blast and helped my family and my self decide on a boat of our own! We can wait to come back out and learn more!

Our family had an absolutely wonderful time sailing in Williamsburg with Captain Bill! He was fantastic—friendly, knowledgeable, patient, and made the entire experience so much fun. He did an amazing job not only making us feel comfortable on the boat, but also teaching us along the way. It truly became an adventure and a learning experience that our entire family enjoyed. We were celebrating my husband’s birthday, and sailing with Captain Bill made his special day even more memorable! Watching our girls enjoy themselves, learn about sailing, and experience something new together was priceless. ❤️⛵️ This was such a special family experience that we will definitely make sailing with Captain Bill a staple event every time we visit Williamsburg! We highly recommend him to anyone looking for a fun, relaxing, educational, and unforgettable sailing adventure. Thank you, Captain Bill, for helping us create such wonderful family memories! We can’t wait to sail with you again! 🌊⛵️☀️

We had a great morning sail with Capt. Bill on his 32' Hunter, and another couple and their 2 cute pups. The pre-trip information and meet-up instructions at the marina were detailed and left no questions. The boat was clean, very well-maintained, and fully equipped. Before heading out he gave us safety instructions and basic familiarization with the boat and its operation. The day was warm and clear, and the wind perfect for relaxed sailing. All 4 of us got a chance to take the helm. We even got to witness a US Navy warship passing us on its way to sea after resupplying at the Yorktown Naval Weapons Depot. The bonus is that Capt. Bill is an expert on the Revolutionary War battle in the Yorktown area and gave us a great history lesson while pointing out locations, and showing artwork depicting the naval battle. We thought his price was very reasonable for this sail trip and would highly recommend it.

What a beautiful day for a birthday sail...too bad the winds did not prevail. All good though, we motored around and enjoyed Capt. Bill's company and that of the other passengers. Was really nice to see some dolphins as well. Bill did offer a refund because the winds just were not there. We hope to join him again at a later date.

You visited colonial Jamestown and Williamsburg, and you glimpsed the edge of the Chesapeake Bay from the Yorktown battlefield monument, perched on a hill that marked the final stage of the Revolutionary War. But what if you could imagine that history from the sea, where the real action took place that served as a defining moment in American history? Capt Bill offers you the chance to do just that, as a guest and crew member on a sailboat that recreates the often-overlooked maritime aspect of the war. Although he may initially come across as a crusty old sailor of yesterday, Capt Bill nevertheless offers a detailed account of the American Revolution by summarizing the key events and personalities that somehow came together to change history. His emphasis on the crucial naval campaign, especially that led by our French allies, is accompanied by historical drawings that depict how the war unfolded. It becomes even more meaningful when you take your turn manning the sail and wheel yourself— realizing how fickle both human nature and Nature herself were during those crucial days 245 years ago. Even if you don’t fancy the Seadog life, this 2+ hour trip is an enjoyable way to experience the area from a unique perspective. Capt Bill knows his history and his sail craft, and you will return from this outing with a fresh appreciation of both.

Awesome experience! Captain Bill was very knowledgeable and a great guide. He really tailored the trip to our family. It was better than we could have expected.

What an amazing day! My husband and I greatly enjoyed our time with Captain Bill. His calm demeanor, historical knowledge, and sailing expertise worked cohesively to give us an experience we won't soon forget. We got to man the helm and learn the fine art of sailing first hand. And to top off an already fantastic day, we saw dolphins! If you're in the area, don't miss Captain Bill's sailing adventure!

We loved our sail with Captain Bill!! Highly recommend

Captain Bill and his sailing experience was wonderful. He was fun and informative and we had a wonderful time. Would highly recommend.

My 16 year-old twins, and I had the best time going out sailing. We learned so much. We all got to steer the boat. The conditions were perfect. Got to learn about harnessing the wind and monitoring our speed. Would definitely recommend it.

We had such an amazing time on this excursion. Captain Bill was very informative, we learned quite a bit about sailing!!! We booked this to celebrate my husband's 60th birthday and it did not disappoint!!! My husband enjoyed being the "captain" for a good part of the sail. We actually got to see a US Navy Sub!!! If you are looking for a fun, informative and exciting day out on the York River, we definitely recommend booking this!!

We had so much fun. We saw dolphins and it was a perfect day for a sail. Captain Bill was very informative and knowledgeable.