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Let's Go Sail Virginia: Unique Sailing Experience
4.9
74 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. Following this, discover the intricacies of increasing speed, interpreting wind patterns, and executing safe turns.
- OPTIONAL: Attend two 20-minute presentations to learn about the French fleet’s victory over the British at the 1781 Battle of the Capes and its role in the…
- York River Yacht Haven - 1. Gain the basics of sailing in just 10 minutes. Following this, discover the intricacies of increasing speed, interpreting wind patterns, and executing safe turns.
- OPTIONAL: Attend two 20-minute presentations to learn about the French fleet’s victory over the British at the 1781 Battle of the Capes and its role in the successful artillery Siege at Yorktown.
- Special Events include Appreciation Cruises, Boat-Buying Cruises, Waterfront Real Estate Cruises, Wedding Engagements, Anniversaries, Birthdays, and Burials at Sea.
- Bring your dog along for free and save on kennel costs.
What's Included
- HEAR an optional short talk on the 1781 battles (please ask).
- 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.
- HEAR an optional short talk on the 1781 battles (please ask).
- 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
Few people get out on the water these days, and fewer still get to sail a modern sailboat. Here is the single-most unique activity in Williamsburg, where guests get to run the helm or just relax on the water. They get to enjoy an optional talk on the two battles that ended the American Revolutionary War. Sometimes they get to see US Navy ships…
Few people get out on the water these days, and fewer still get to sail a modern sailboat. Here is the single-most unique activity in Williamsburg, where guests get to run the helm or just relax on the water. They get to enjoy an optional talk on the two battles that ended the American Revolutionary War. Sometimes they get to see US Navy ships transiting Yorktown.
- 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
(74 Ratings)
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Donnase5215sz
Jul 13, 2025
Wonderful Sail - Captain Bill was amazing and so informative. Taught us a lot and took fantastic pictures for us. What a great first sail experience.
Review provided by Tripadvisor
X8665syjiml
Jul 9, 2025
Wonderful - So much fun, beautiful experience! A great time,felt very safe on the sailboat.Friendly Captain!!! Very nice time, would do it again
Review provided by Tripadvisor
655suef
Jul 7, 2025
Fun Sailing Experience! - We were looking for a smaller sailing experience, rather than being one of many on the large tourist boat. This checked all the boxes. Sailing on the York River, taking the helm, and putting up the spinnaker sail. Captain Bill has a beautiful boat, well maintained. He was easy to communicate with and he sent us some nice pictures. Highly recommend! After the sail, we enjoyed a delicious lunch at the marina restaurant.
Review provided by Tripadvisor
895efrenc
Jul 5, 2025
Surprise tour for the Wife - Brought my wife for the boat tour and the fact that pets are okay to join at no extra cost made it even better for all of us without the hassle. The sponsor was great, sincere, communicative for any occasion, and hospitality.
Review provided by Tripadvisor
Burger522
Jul 4, 2025
Beautiful day of sailing, and we saw glorious dolphins!! 😍🐬 - This was SUCH a great day - just our family with the captain and first mate, and it was a peaceful day on the water.
We even saw podS - PLURAL - of dolphins! They were so close, it was magical.
It’s not a “sightseeing” trip per se, but rather a chance to get out on the water and do something new. We got to learn the feel and some of the science of sailing as well.
It was an awesome day. ♥️
Review provided by Tripadvisor
Mikewj3090wm
Jul 1, 2025
Time on the water with a Great and experienced captain. The whole family loved it! - My family spent the week in Williamsburg to show my daughters first hand what they had learned in Virginia History this school year. Our plans changed when everyday that we were there the temps were near or over 100 degrees and many of the outside history museums closed early. I searched online and came across this sailing experience with Williamsburg Charter sails. I quickly noticed the trip was 3 hours and only cost $250 for up to 6 people!
From the moment that I reached out to Williamsburg Charter Sails to book our sail to the moment that we docked, I was nothing but impressed the entire way. The communication was great! The details were spot on and there were no hidden fees or agenda.
We set sail and enjoyed the cool York River breeze for 3 hours. My entire family was given the opportunity to captain the boat, to sit up front and the relax with the river breeze. Captain Bill was absolutely wonderful. He is full of experience and really made the trip enjoyable. He took pictures along the way to capture our sail. That evening he emailed the photos, no extra cost.
If you’re looking to get out on a cruise this is the way to go. Most cruises leave you wanting more and this one at 3 hours gives you time on the water. I can’t say enough for the Captain!! Thank You!!
Review provided by Tripadvisor
Toni_w
Jun 30, 2025
Beautiful Boat with Engaging Captain - Booked this activity as a birthday outing for our 17yo nephew and he loved it. Captain Bill adjusted the schedule to wring the best weather out of a hot, humid day then almost immediately put the 17yo at the helm. Although a tourist now, I grew up in the area and can say I've done just about everything there is to do. This is in my top 3 of activities.
Review provided by Viator
607leslief
Jun 25, 2025
A perfect, peaceful sail! - We had a blast on Capt. Bill's beautiful, spacious vessel! He's an excellent sailor (always important!) and a great guide to the York River and sites surrounding it. GReat history lesson! This was a birthday celebration, and it was just what I wanted. He even accommodated my desire to forego music while on board, which made it the idyllic, peaceful excursion that I'd wanted. You can't go wrong with Capt. Bill. Just do it!
Review provided by Tripadvisor
840bethn
Jun 22, 2025
Captain Bill's Sailing Experience is fantastic!!! - This trip was a blast! We didn't realize we'd actually have an opportunity to steer the boat, but we did and it was a great experience. Captain Bill is fantastic. He is very knowledgeable about the sailing process, the history of the general area, and overall a great tour guide. Would highly recommend!
Review provided by Tripadvisor
Stephaniec20201990
Jun 20, 2025
Best Birthday ever - Great opportunity to get a chance to sail. It was definitely one of the most memorable experiences of my life. Captain Bill was great at guiding and teaching us how to sail and we even got an opportunity to take the helm. What a wonderful 35th birthday gift.
Review provided by Tripadvisor
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