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Let's Go Sail Virginia: Unique Sailing Experience
4.9
107 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, you’ll discover how to increase speed, interpret the wind, and safely maneuver the boat.
- Special events include Appreciation Cruises, Boat-Buying Cruises, Waterfront Real Estate Cruises, Wedding Engagements, Anniversaries, Birthdays, and Sea Burials.
- Bring…
- York River Yacht Haven - 1. Gain the basics of sailing in just 10 minutes. From there, you’ll discover how to increase speed, interpret the wind, and safely maneuver the boat.
- 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 allowed!
- 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
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
(107 Ratings)
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1 star
Asoalexander
Nov 28, 2025
Best Boat in Virginia! - You will not find a better value or a better experience anywhere. Our captain was incredibly knowledgeable, genuinely friendly, and his pricing is more than fair for what you get. Coming from Florida, we’ve spent plenty of time with different boat captains over the years — and he is truly in a league of his own.
We took the historical tour, and I cannot recommend it highly enough. His understanding of Revolutionary War history is unbelievable. It felt like we were getting a behind-the-scenes, VIP walkthrough of a History Channel documentary, brought to life right in front of us.
If you’re even thinking about booking, do it. This was easily one of the highlights of our trip. Highly, highly recommended!
Review provided by Tripadvisor
Resort24803240664
Nov 2, 2025
Wonderful Day Sailing with Captain Bill - My best friend and I had a wonderful time sailing with Capt.Bill. The views were amazing. It was incredibly relaxing and much needed time together bonding . I will definitely be booking again.
Review provided by Tripadvisor
Nonamer525
Oct 28, 2025
First Sail - It was a great three hour trip. Our Captain was very knowledgeable in not only sailing but the history of the area itself
All in all couldn't ask for anything more
Review provided by Tripadvisor
Terry
Oct 11, 2025
First time Sail boat ride - Capt Bill was great. He made the trip very enjoyable and allowed everybody to participate. The experience was amazing and worth it
Review provided by Tripadvisor
Jennifertb8997ef
Oct 7, 2025
Sail, sun, and friends!! - Capt Bill shared his boat and the afternoon with us. It was just the best time!! He shared American history, pointed out areas of interest, and allowed us to manage the boat under his direction. I recommend this highly. It was a great day and great time
Review provided by Tripadvisor
Lavb
Sep 27, 2025
Anniversary Sail - My husband and I took a quick/small get away trip for our 30th Anniversary. We live only 3 hours from Williamsburg and have visited there and Yorktown a few times over the last 5 years. We were literally making plans on the drive. We landed on Captain Bill's "Let's Go Sail Virginia" site through TripAdvisor and were so happy we did. The weather was beautiful and we got to experience "hands-on sailing". Captain Bill is funny and has wonderful stories of the battles that took place on the waters around Yorktown. You can tell, he loves sailing and loves the connection with his passengers. We had a very "neat surprise" connection to our hometown. This was a 10/10 experience for my husband and I, and we highly recommend booking a sailing experience with Captain Bill. The first photo I'm attaching was actually taken by Captain Bill and belongs to his gallery. He was great and shared this with us. What a great memory photo to have for our trip.
Review provided by Tripadvisor
Marksc3198em
Sep 27, 2025
Awesome - My wife and I enjoyed an awesome sail!
Beautiful boat and extremely knowledgeable Captain.
I would highly recommend lets go sail Virginia!!
Review provided by Tripadvisor
Leehasenauer
Sep 25, 2025
Is there anything better than sailing? - I sailed with Captain Bill and five veterans on a 3-hour tour of the York River. Thankfully, we had perfect weather and conditions. Captain Bill encouraged each of us to relax at times and also to help with tasks like manning the helm and tacking. The experience was at the same time relaxing and educational, as Captain Bill taught basic sailing skills, history, and local area facts. The atmosphere onboard the sailboat was perfect: stress-free, tidy, and safe. The vessel was just the right size for me: large enough to spread out yet small enough to feel immersed in the sailing experience. I really couldn't ask for a better day on the water. I will definitely return for another sailing excursion with Captain Bill.
Review provided by Tripadvisor
Ohiostate
Sep 24, 2025
6 stars out of 5! Fabulous adventure. - Captain Bill provided a fabulous sailing experience on the York River. We had a wonderful time and even learned about some history. Water and ice were provided. So happy we had the opportunity to enjoy a relaxing afternoon with Captain Bill. There were 4 of us on our sailing adventure. Definitely recommend Captain Bill. I would rate this 6 out of 5 if I could. Thank you again from your Ohio friends!
Review provided by Tripadvisor
Freedom48998823607
Sep 21, 2025
Relaxing and informational - Definitely worth the price especially for couples. Captain Bill is very friendly and extremely knowledgeable not only about sailing but also about the area and history of the area. Would recommend if you a novice sailor or a beginner.
Review provided by Tripadvisor
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