Private York River Sailing Adventure

Experience the thrill of sailing on the York River in Gloucester Point. Sail your own 32-foot sloop or relax on deck for a romantic and private outing. Perfect for engagements, birthdays, anniversaries, or surprise gifts.

Duration: 2 hours, 30 minutes
Cancellation: 24 hours
Highlights
  • York River Yacht Haven - Discover the region’s premier private sailing adventure just a short distance from Williamsburg and Yorktown. Board a cozy 32-ft sloop for a serene, interactive sail on the picturesque York River, where consistent breezes, expansive waters, and breathtaking views offer the finest sailing conditions in Tidewater Virginia….
What's Included
  • Privacy on a cushion up on the bow.
  • Bottled water
  • Learn to sail in 20 minutes. Grab the helm!
  • Run the helm as you learn to sail. Hoist the spinnaker for downwind sailing. Swim off the aft if the wind dies.
  • Photos provided for free of your excursion.
What's Not Included
  • Absolutely no illegal drugs onboard.
Additional Information

Couples and families have the special chance to navigate their own 32-foot sloop, equipped with all modern amenities. Alternatively, they can unwind in the cockpit or on the bow for added privacy. This is a fantastic option for engagements, birthdays, anniversaries, or as a surprise gift.
Enjoy private, interactive sailing on the stunning York River,…

Location
York River Yacht Haven
Yacht Haven Road
Park near the pool and go to the nearby Magnolia tree. I'll meet you there.
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Customer Ratings
5.0
(170 Ratings)
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Carisseb
Oct 25, 2026
York River sailing - 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.
Review provided by Tripadvisor
Christinecm5167li
Oct 24, 2026
A great afternoon sailing! - 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!
Review provided by Tripadvisor
Explore14191887193
Oct 23, 2026
Exceptional Experience! - 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!
Review provided by Tripadvisor
Amanda_l
Oct 6, 2026
A must do - 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.
Review provided by Viator
Roving17605779371
Sep 21, 2026
Fun, hands-on sailing trip - 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!
Review provided by Tripadvisor
Shel03
Sep 5, 2026
Captain Tom was awesome! - 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.
Review provided by Tripadvisor
Aartihavaa
Aug 21, 2026
Water and wisdom therapy with a great captain - 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.
Review provided by Tripadvisor
Hrhiii
Aug 19, 2026
Fabulous experience - 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.
Review provided by Tripadvisor
Tourist02010506962
Aug 12, 2026
Wonderful sailing - 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.
Review provided by Tripadvisor
G8624onmelindas
Aug 10, 2026
Wonderful time - Had a wonderful time, Captain Bill was great
Review provided by Tripadvisor
From $96
up to 6 guests
1 - Adult
Cancellation: Free cancellation up to 24 hours before the start of your experience (local time).