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York River Sailing: Unique Gloucester Point Experience
5.0
145 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 to steer the vessel, learn the fundamentals of sailing, delve into captivating local history, or simply unwind on deck. Spot dolphins during the warmer months, enjoy 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
(145 Ratings)
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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
Amanda_j
Oct 6, 2025
Captain Bill will work with your group! - I loved my first time sailing! Went with other Christian business owners while visiting Williamsburg for a work conference. Loved that Captain Bill was flexible with our wants. He even delivered us back early so we could get back in time for an evening meeting.
Review provided by Viator
A_h
Oct 6, 2025
Doesn’t get any better on a deadline. :) - It was WONDERFUL. Captain Bill is so Experienced and Friendly
So relaxing and Smooth Sailing
The wweather was Perfect
And I was deck hand :)
Review provided by Viator
Kencl7718mw
Oct 5, 2025
Relaxing fun day out on the water. - We got extremely lucky with a beautiful day out on the water. The captain taught us how to sail by showing us how to read winds directions and how to use nautical instruments. We will share our experience with friends and family. Thank you captain for a wonderful experience.
Review provided by Tripadvisor
H3812wacharliet
Sep 13, 2025
Maximum fun at a 15 degree heel - What a fantastic trip. Captain Bill has a well maintained and very clean boat. What an amazing adventure; so much better than any other sailing tour I've done. We deployed the sails as soon as we left the no wake zone and didn't put them away for 2 1/2 hours when we came back to dock. Yes, it helped that the weather was perfect and we had good winds.
Great history of the bay that paired beautifully with our Colonial Williamsburg trip just down the road. The history lesson we asked for showed the Revolutionary War through the eyes of the bay, which most historians don't bring to life. No better way to "stand on the battlefield" than on a sailboat on the water.
The captain was kind enough to let me helm the boat for the whole sailing portion and I was delighted. One of my favorite memories over 30 years ago was the quiet sound of the wind and the waves, going fast while heeling. No obnoxious motor with diesel fumes. I relived those memories and basically grinned nonstop for over two hours. Thank you, Captain, for such a wonderful birthday memory.
I'm doubly amazed at the fantastic value. Private charter is absolutely the way to go. These tours make an awesome date no matter your age. Captain Bill is an ace at keeping the nautical lingo to a minimum so we could make the most of our time enjoying our trip, learning only as much about sailing as we wanted to.
Review provided by Tripadvisor
Michaellb2741hj
Sep 13, 2025
The Best Captain And A Relaxing Afternoon - Bill was incredible! My girlfriend and I cruised with Bill on a beautiful September day. Bill is so friendly, a genuine pleasure to talk with, super knowledgeable about sailing. We had such a relaxing afternoon as a couple with Bill as our captain. I highly recommend Williasmburg Charter Sails to anyone looking for a fun, relaxing, and enjoyable day on the water!
Review provided by Tripadvisor
Irish69th
Sep 1, 2025
You must sail with Capt Bill - This was our 4 or 5th time sailing with Capt. Bill. It was excellent. Clean modern ship will the needed necessities. Capt. Bill was relaxed, informative and friendly. The sailing was smooth with the mainsail and jib in action. A pod of 3 porpoises joined us for the last leg of the outing. Excellent ship and skipper. I highly recommend that you sail with Williamsburh Charter Sails.
Review provided by Tripadvisor
462salliep
Aug 31, 2025
Captain Bill is a great sailing instructor - My sons and I had a GREAT time! Captain Bill was very knowledgeable and helpful in assisting us with getting sea worthy! He included us all in on the various aspects of sailing and historical information about the area we sailed in.
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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