York River Sailing: Unique Gloucester Point Experience

Families and couples have the special chance to navigate a 32-foot sloop, equipped with all the contemporary facilities. Alternatively, they can unwind in the cockpit or on the boat’s bow for more solitude. Ideal for celebrating engagements, birthdays, anniversaries, or as an unexpected gift.

Duration: 2 hours, 30 minutes
Cancellation: 24 hours
Highlights
  • York River Yacht Haven - Couples, friends, and families can enjoy a 2.5-hour cruise on the stunning York River. Participants have the opportunity to learn sailing or simply unwind. It’s perfect for a romantic escape.
What's Included
  • Privacy on a cushion up on the bow.
  • Bottled water
  • Run the helm as you learn to sail.
  • Hoist the spinnaker for downwind sailing.
  • Swim off the aft if the wind dies.
  • Learn to sail in 20 minutes.
  • Photos provided for free of your excursion.
What's Not Included
  • Absolutely no illegal drugs onboard.
Additional Information
  • 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.

Customer Ratings
5.0
(135 Ratings)
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1 star
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!
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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.
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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.
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Curiosity60188220266
Aug 23, 2025
Relaxation & Dolphins! - 10/10 - Capt Bill was great! My husband and I luckily had the boat to ourselves so we had a nice relaxing sail on the water. Capt Bill gave us both a sailing and a history lesson. He was extremely knowledgeable and we felt very safe with him. BEST PART is we saw so many dolphin!! They swam by our boat and were playing in the water! Very memorable activity!
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Tedwhixson
Aug 16, 2025
Great Sailing Trip!! - Capt. Bill was great. Although there was not much wind, it was still very enjoyable for my wife and I to celebrate our anniversary. The historical stories added to the fun.
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Rxgirl2003
Aug 16, 2025
Highly recommend! - Great experience! Part sailing lesson, part history lesson, part relaxing afternoon on the water. Captain Bill was knowledgeable, well prepared, patient, and a pleasure to spend a couple hours with. Highly recommend!
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Fearless08094065408
Aug 13, 2025
Best Ever Cruise - It was a wonderful time on the water. I knew my guests would find the history tour interesting, which they did. Fascinating. Afterwards, at lunch at the oyster bar, they gushed enthusiastically about you, the adventure and, especially about your smooth and thorough historical information...all without notes, they noted!! Great day, it was. And, it was fun for you to let me take the helm, an exhilarating time. Certainly will pass along the good word about your operation! Again, super time and with such a terrific host!
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Chirag483
Jul 29, 2025
Relaxing day sailing - We had a family of four, and the experience was wonderful. Captain Bill clearly has a lot of experience and was wonderful during the whole trip. He let those of us who wanted to steer, enjoy the experience. The kids had a great time, and the York river is really peaceful and not crowded. Highly recommend, and thanks Captain Bill for a great day on the water!
Review provided by Tripadvisor
859deedeec
Jul 29, 2025
Great sailing trip - We had a nice calm sailboat trip. Not much wind but the Captain knew how to find it! Traveled out by Coleman Bridge. Got to watch a bridge opening for a Navy ship to pass through.
Review provided by Tripadvisor
From $96
up to 6 guests
1 - Adult
Cancellation: Free cancellation up to 24 hours before the start of your experience (local time).