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York River Sailing: Unique Gloucester Point Experience
5.0
161 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
(161 Ratings)
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Tourist02010506962
Aug 12, 2026
Wonderful sailing - Excellent sailing. Our captain Bill was wonderful. I would have liked to know where to meet Bill beforehand. Other than that it was wonderful. I would recommended to anyone.
Review provided by Tripadvisor
G8624onmelindas
Aug 10, 2026
Wonderful time - Had a wonderful time, Captain Bill was great
Review provided by Tripadvisor
Patriciasz1791qd
Jul 30, 2026
Fun afternoon sailing! - Had a great time with Capt Bill! He kept us apprised of the conditions a few days in advance which was nice as we had to travel 2 hrs to get there. It’s a cozy sail with a few folks, we had a blast with a family from Nebraska with roots to Kansas City, same as us! It’s was a partly cloudy day and we just sailed around and relaxed. We did enjoy the cafe and grill on site at the marina.. great food and service. We went on a Tuesday and did the 11 AM tour.
Review provided by Tripadvisor
Scottrw700jd
Jul 19, 2026
Fun afternoon on the water - This was one of the best experiences I have booked through trip advisor and at a very reasonable price. Captain was knowledgeable and allowed guests to have a hands on experience if they chose to do so. We were fortunate to have excellent conditions the day we went. Highly recommend. The restaurant at the marina is also worth grabbing lunch at after.
Review provided by Tripadvisor
723randyp
Jul 6, 2026
Great Holiday Weekend Sail - We had a great experience with Captain Bill. He was very knowledgeable and a great teacher/communicator. It was a hands on experience for a few of us, which was an added perk.
I would definitely trust Capt. Bill to cross the Potomac River any day of the week.
Review provided by Tripadvisor
806rheanar
Jun 27, 2026
Amazing birthday of my life - The yatching experience was amazing. I would go on it again my family. Although I have to practice multiple times to sail the boat better.
Review provided by Tripadvisor
Lisaob5812xc
Jun 22, 2026
What super way to relax and enjoy your day - Took our grandson for a first time experience for all of us. What a wonderful way to spend the day. Captain Bill was booked for the day but made sure we could enjoy the day making accommodations for us to go out with Captain Bob. We all enjoyed our day immensely would highly recommend for anyone interested in sailboating will go back. Thank you!!!!!
Review provided by Tripadvisor
Stacycf8020va
Jun 22, 2026
Father’s Day Sail - Phenomenal Father’s Day sail with Capt Bill! Very peaceful, laid back afternoon on the York River. My husband has been interested in sailing and he absolutely loved it! Bill is so informative with years of experience and let hubby sail! Memorable trip!
Review provided by Tripadvisor
Jet07484041267
Jun 16, 2026
Delightful day sailing with Williamsburg Carter Sails - We enjoyed a delightful day sailing with Captain Bill from Williamsburg Charter Sails. Bill was absolutely wonderful with our group of 11 high school boys - most of whom had never been on a sailboat. This turned out to be an experience of a lifetime for many of the boys. Bill was patient and knowledgeable. He gave a clear, easy to understand introduction to sailing - and also - found time to share stories and tidbits of local history and to point out the interesting landmarks we were passing. We also saw pelican, osprey, and other sea birds. Later, we came across Naval Academy training activities and saw a hovercraft taking off. Our students loved the whole trip and continued to discuss the experience through lunch. And then, to top things off, Captain Bill snapped a bunch of photos and sent some beautiful images to us the very next day! The guys loved that too. We highly recommend Williamsburg Charter Sails and would love to find a time to get back on the water with Captain Bill.
Review provided by Tripadvisor
310antonioc
Jun 19, 2026
Good hotel, good meal, cleanliness, but critical location with the road... - We requested 4 double rooms, we received 4 times 2 separate beds! You talk about the sandy beach, the concept of beach needs to be reconsidered; stones, pebbles, no way to walk along the beach. You must clear 4 meters of cobblestone, large irregular stones, before having a bit of sand in the water. False advertising because we wanted a sandy beach; there is a concrete promontory where lounge chairs are set up, large sand, you had to have special shoes to walk or go into the water, it was difficult even to keep your balance when entering and exiting the water, risk of injury!!!! No fresh fruit juice, you had to pay for fresh orange juice!!!! and then you mention that there is a road, clearly specifying that it is not a low-traffic road but almost a highway, with motorcycles, cars, buses, a deafening noise whether you are at the hotel, in the restaurant, or on the beach. It's a shame because it's a beautiful hotel, with pleasant and helpful staff. A lovely discovery, the squirrels. Very good and varied meals. The hotel is clean, but you need to be more honest when selling a stay with no sandy beach! A road that makes a deafening noise! Paid orange juice! I also have videos showing that we lose our balance when entering and exiting the water! Impossible to walk along the beach!
Review provided by Tripadvisor
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