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 an excellent choice for a romantic escape. An optional brief history tour highlights the 1781 battles that secured America’s independence.
What's Included
  • Bottled water
  • Learn to sail in 20 minutes
  • Take the helm yourself
  • Hoist the spinnaker for downwind sailing
  • Swim off the aft if the wind dies
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
(122 Ratings)
5 stars
4 stars
3 stars
2 stars
1 star
379toniw
Jun 30, 2025
Beautiful Boat with Engaging Captain - Booked this trip as a birthday outing for our 17yo nephew and he loved it. Captain Bill was a great host, teaching us about sailing in general, the York River and the Chesapeake Bay. He also took great pictures and had them to us early the next morning. We happened to book for a particularly hot day and Bill adjusted our departure time to insure the best weather for both our comfort and sailing. As a tourist returning to the area where I grew up, I think I've done everything there is to do and sailing the York has to be in my top 3 activities.
Review provided by Tripadvisor
Cathykp3733ai
Jun 21, 2025
Great lesson on a Hunter 32 - This was such a fun day. We went on the lesson cruise where we got to steer the boat. Captain Bill was amazing captain and host. There were only 6 of us so we all got plenty of time at the helm. I highly recommend this sailing cruise.
Review provided by Tripadvisor
Stevefm4755bp
Jun 11, 2025
Relaxing day sailing the bay - We couldn’t have asked for a better day on the water. Captain Bill was incredibly informative sharing the history of the Yorktown battles in the Bay and on land. In addition we learned a tremendous amount about sailing.
Review provided by Tripadvisor
S4698wpdalew
Jun 1, 2025
Beautiful day on the York River - We had a wonderful time on the water! Bill the captain was a delight and very knowledgeable. A great teacher and guide. Suitable for any small group.
Review provided by Tripadvisor
Robert_r
May 26, 2025
Calm seas and lite winds... - Calm seas and lite winds created the perfect time on the water. Capt. Bill was extremely knowledgeable about the battle of Yorktown.
Review provided by Viator
N4635apkenm
May 21, 2025
Excellent Adventure. - Excellent! Relaxing! Just enough hands on to make us think We were sailing, but Captain Bill was always right there when it got too exciting.
Review provided by Tripadvisor
Tmpnqn
May 1, 2025
Great Sail! - My husband, who is in a wheelchair but can transfer, and I did this sail today. It was wonderful! Captain keeps you informed, sends detailed directions on how to find him, and the boat is beautiful. We had a lovely relaxing sail, great conversation, and laughed a lot. He even recommended the restaurant at the marina which was fabulous. Highly recommend!
Review provided by Tripadvisor
Kellydw5770yu
Apr 10, 2025
Afternoon sail - Great afternoon sail. Captain Bill is a good guy. Would recommend if you enjoy the water. The sail was worth the money spent!
Review provided by Tripadvisor
E3791cpamandaf
Oct 20, 2024
Best maiden sailing voyage! - Captain Bill gave us a wonderful sailing experience. We used this experience to see if owning a sailboat is in our future. We were able to learn the basics of sailing and Captain Bill further stoked the flames for our desire to take up sailing! Thank you for such a great experience!
Review provided by Tripadvisor
Pamelamx7133pj
Oct 11, 2024
Great Sail as a Team - We took a team appreciation Cruise with Captain Bill and had the most fabulous day! We all were taught how to sail, enjoyed a beautiful day on the York River, and had the dolphins swim along side us! This was such a great experience, and Bill was the perfect host for our team retreat!
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).