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York River Sailing: Unique Gloucester Point Experience
5.0
148 Ratings
Gloucester Point
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.
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….
- 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. Each charter is exclusively private (up to 6 people), allowing you the opportunity to steer the vessel, learn the fundamentals of sailing, or simply unwind on deck. Observe dolphins during the warmer months, take in the vast river vistas, and escape the crowds for an unforgettable experience ideal for couples, families, and anyone in search of a genuine coastal adventure. Perfect for a romantic getaway.
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.
- 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.
- 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,…
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, just a short distance from Williamsburg. Take the helm, discover local history, watch for dolphins, or simply relax. This is a serene and unforgettable experience for couples, families, and anyone looking for the region’s premier sailing adventure.
- Friendly dogs welcomed.
Location
York River Yacht Haven
Yacht Haven Road
Park near the pool and head east to G Dock.
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
5.0
(148 Ratings)
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Robert_s
May 18, 2026
Sail York town River Virginia - My wife and I had a wonderful day with Captain selling on the Yorktown River hearing about the history and battles that occurred there.
Review provided by Viator
B6345ezsallyl
May 15, 2026
Set Sail o the York River - It was a beautiful day to be on the water. Bill shared historical highlights of the area and provided opportunities to learn a little bit about sailing. I would highly recommend this excursion!
Review provided by Tripadvisor
G2674faelizabethb
May 11, 2026
3 girls and a guy's day on the water - It was a very relaxing, intimate and quaint environment on Bill's boat. He was very knowledgeable about the area and the associated history. He lent me a sweatshirt since I left my jacket in the car. He also found my Key West visor that I left behind and promised to mail it to me. He let several adult passengers drive the boat.
Review provided by Tripadvisor
658mendym
May 2, 2026
Set Sail - My husband and I celebrated our Wedding Anniversary by sailing (1st time ever for us) down the York River in Gloucester, Va. I got to man the helm while my Hubs sat back and enjoyed the ride. It was a great day for sailing! It was a sunny 62 degrees, light breeze (until we picked up speed! Then it was chilly!!!!) and calm waters. We are so grateful for Capt. Bill, who was so full of historical knowledge and a wonderful instructor on the how-to’s in sailing. We definitely recommend and we will be back again!!!
Review provided by Tripadvisor
Wander06479821832
Apr 18, 2026
Definitely worth the money, we would absolutely go again the next time we come here. - We had a great time, the captain was really fun. And he let my husband drive the whole time, the weather was absolutely perfect.
Review provided by Tripadvisor
Lwj90
Mar 30, 2026
Great day sailing the York - Bill showed our 13 year old grandson how to sail his 32 foot long sailboat and he loved it. He taught him how to set the sails for light winds and when the wind is faster.
Declan was at the helm for about 20 of the 23 miles we sailed. Highly recommend.
Review provided by Tripadvisor
722daniellek
Mar 15, 2026
Gloucester Area Cool Adventures - We were the first sailing tour of the season on a brisk March day when we were visiting the Gloucester area. My husband has always wanted to sail and we wanted to learn more about the area so I found this tour thru Tripadvisor.
Reading other reviews it looked a little early to go out but it was the only time that worked for us so I took a chance and reached out to see if we could arrange a tour. Bill worked around our schedule and made it happen for us.
It was colder than we had figured but Bill had gloves and hats and it made for a good sailing breeze...
My husband got to learn and operate the boat most of our trip, which he absolutely loved! Our teenage daughters and I enjoyed the scenery and learning about Yorktown. The starting point was easy to find, right by a really great seafood restaurant, Yrocks.
This was a very laid-back, great introduction to sailing, -and very reasonably priced- which is exactly what we were looking for!
Review provided by Tripadvisor
G8008wyjennyc
Oct 28, 2025
End of season overcast day wonderful exhilarating experience with Captain Bill's sailing lessons. - My husband at the helm, Bill's calm confident instructions made the trip one of the delights of my life. If youre in the area take a sailing lesson or just a sailing excursion, it won't disappoint.
Review provided by Tripadvisor
Navigator43532821678
Oct 23, 2025
An Unforgettable Sail with Captain Bill! - We had a fantastic sailing excursion today, and it was hands-down one of the highlights of our trip! Captain Bill was an absolute standout – witty, professional, and incredibly knowledgeable about Revolutionary War naval battles. He shared fascinating stories and historical insights that brought the water to life, making our sail feel like a journey back in time.
The boat was spotless, the weather couldn't have been better, and Captain Bill's seamless navigation kept everything running smoothly. We even got the opportunity to watch dolphins escorting us back to the marina. Whether you're a history buff or just looking for a relaxing adventure, this is a must-do. We can't recommend it enough – book it now!
Review provided by Tripadvisor
Dale_c
Oct 13, 2025
A windy, cold day on the water. - This is a good experience if you want to captain a sail boat. Otherwise, it is just a nice sail around the James River and you need to hope for good weather. The day we went out it was quite choppy, cold and windy. We were glad when it was time to return to the dock. Bill the Captain is nice and tried to make the trip fun.
Review provided by Viator
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