Recently Viewed
Let's Go Sail Virginia: Unique Sailing Experience
4.9
165 Ratings
Gloucester Point
Experience Williamsburg’s unique sailing adventure. Steer a modern sailboat, relax, and learn about historic battles. Spot US Navy ships in Yorktown.
Experience Williamsburg’s unique sailing adventure. Steer a modern sailboat, relax, and learn about historic battles. Spot US Navy ships in Yorktown.
Duration:
2 hours, 30 minutes
Cancellation:
24 hours
Highlights
- York River Yacht Haven - 1. Gain the basics of sailing in just 10 minutes. From there, delve into mastering speed, interpreting the wind, and executing safe turns.
- Special events include Appreciation Cruises, Boat-Buying Cruises, Waterfront Real Estate Cruises, Wedding Engagements, Anniversaries, Birthdays, and Sea Burials.
- Bring your dog…
- York River Yacht Haven - 1. Gain the basics of sailing in just 10 minutes. From there, delve into mastering speed, interpreting the wind, and executing safe turns.
- Special events include Appreciation Cruises, Boat-Buying Cruises, Waterfront Real Estate Cruises, Wedding Engagements, Anniversaries, Birthdays, and Sea Burials.
- Bring your dog along at no extra cost and save on kennel fees. Cats are not permitted.
- Relax and unwind, or enjoy private moments at the bow for couples.
What's Included
- CELEBRATE your anniversary or birthday with private seating on a cushion up on the bow.
- Dinner
- PHOTOS offered for free of the entire crew at sea, and on the wheel.
- DOGS are welcome, and sometimes they attract dolphins (true fact).
- Lunch
- LEARN to sail by taking the helm (wheel) to turn the boat.
- CELEBRATE your anniversary or birthday with private seating on a cushion up on the bow.
- Dinner
- PHOTOS offered for free of the entire crew at sea, and on the wheel.
- DOGS are welcome, and sometimes they attract dolphins (true fact).
- Lunch
- LEARN to sail by taking the helm (wheel) to turn the boat.
What's Not Included
- No drugs and no cats!
- No drugs and no cats!
Additional Information
Nowadays, not many people venture out onto the water, and even fewer have the chance to sail a contemporary sailboat. This is the most distinctive activity in Williamsburg, offering guests the opportunity to take the helm or simply unwind on the water.
In contrast to crowded tourist vessels, each charter here is completely private. Guests can navigate…
Nowadays, not many people venture out onto the water, and even fewer have the chance to sail a contemporary sailboat. This is the most distinctive activity in Williamsburg, offering guests the opportunity to take the helm or simply unwind on the water.
In contrast to crowded tourist vessels, each charter here is completely private. Guests can navigate the yacht, adjust the sails, or just relax while enjoying expansive river views, observing local wildlife, and feeling the consistent coastal breeze that makes the York River the premier sailing waterway in the area. Dolphin sightings are frequent during the warmer months.
Ideal for:
• Couples seeking a unique, romantic experience
• Families desiring a safe, private adventure
• History enthusiasts exploring Williamsburg and Yorktown
• Photographers and wildlife lovers
• Anyone searching for the finest sailing near Williamsburg, VA
Whether celebrating a special occasion or simply wanting to experience the York River under sail, this is the region’s top-rated, most genuine sailing experience.
- ADA accessible with 24-hour notice.
- Shade and padded seat provided.
Location
York River Yacht Haven
Yacht Haven Road
Simply set your GPS to York River Yacht Haven. Park for free at the nearby marina pool and head to G Dock. I'll meet you there.
Cancellation Policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
For a full refund, cancel at least 24 hours before the scheduled departure time.
Customer Ratings
4.9
(165 Ratings)
5 stars
4 stars
3 stars
2 stars
1 star
Leah_w
Aug 19, 2026
Awesome Captain Bill 🤙🏾 - 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!
Review provided by Viator
Sizzlingsisig
Aug 16, 2026
Ahhhhmazing! - 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!
Review provided by Tripadvisor
Matthewsz1199xt
Aug 12, 2026
Worth every penny! - 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!
Review provided by Tripadvisor
Nicolejv7502ap
Aug 11, 2026
An Amazing Sailing experience with Captain Bill! - 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! 🌊⛵️☀️
Review provided by Tripadvisor
Jackm954
Aug 10, 2026
A Great Day Sailing on the York River with Captain Bill O'Donovan - 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.
Review provided by Tripadvisor
Lesfroggies2011
Aug 4, 2026
Set sail for a unique appreciation of US history! - 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.
Review provided by Tripadvisor
Voyager17985650841
Aug 2, 2026
Great sailing experience - 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.
Review provided by Tripadvisor
Amykr48
Aug 1, 2026
A Memorable Day! - 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!
Review provided by Tripadvisor
Fearless32679507432
Jul 30, 2026
Wonderful Sail - We loved our sail with Captain Bill!! Highly recommend
Review provided by Tripadvisor
Z9584xhdenises
Aug 10, 2026
Very enjoyable birthday outing! - 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.
Review provided by Tripadvisor
More activities from this operator
