Williamsburg Charter Sails offers private and small-group sailboat charters on the York River, sailing out of York River Yacht Haven in Gloucester Point, Virginia. Located a short trip across the Coleman Bridge from Yorktown, and about 17 miles from Williamsburg, Williamsburg Charter Sails gives visitors and locals an easy way to get out on the water for a few hours without owning or crewing a boat themselves.

Every charter goes out on a 32-foot Hunter sailboat equipped with in-mast furling, oversized sails for speed, and a colorful spinnaker for light downwind sailing. The boat is powered by a Yanmar diesel engine for maneuvering in creeks and calm conditions, and it’s maintained to U.S. Coast Guard standards with clearly marked, color-coded rigging. Charters are led by a licensed captain holding a 100-Ton U.S. Coast Guard credential, who has also taught through the American Sailing Association and brings a strong knowledge of local Revolutionary War history along the York River.

Williamsburg Charter Sails runs six distinct charter experiences, so guests can choose the trip that fits their reason for being on the water:

– Adventure Cruise – the most popular option, where guests can take the helm and actively crew the boat
– Event Cruise – a scenic backdrop for anniversaries, birthdays, proposals, and other celebrations
– Appreciation Cruise – built for employers who want to take their team out for a relaxed, phone-free retreat
– History Cruise – covers the 1781 Battle of the Capes and the Battle of Yorktown as seen from the York River
– Lessons Cruise – a short, beginner-friendly course through the onboard sailing school
– Boat Buyer Cruise – for anyone considering buying a sailboat and wanting real time on the water first

Cruises depart daily at 11:00 a.m. and 2:30 p.m. and run about 2.5 hours. Pricing is based on group type:

– Couples/Semi-Private charter: $150, ideal for couples or friends traveling together, with the boat potentially shared with up to two other couples
– Family charter: $250, for 3 to 6 related people (kids 12 and up are recommended)
– Group charter: $350, for 4 to 6 unrelated people, with an optional sailing lesson included

Bottled water is provided on every charter, and guests are welcome to bring their own food or snacks aboard. Williamsburg Charter Sails also allows dogs to join charters at no additional cost, making it a good option for travelers who don’t want to leave a pet behind.

Because charters sail on the York River near where it meets the Chesapeake Bay, guests get a mix of open water, calmer creek sailing, and views tied to the region’s Revolutionary War history, including sites connected to Yorktown. This makes Williamsburg Charter Sails a fit for several different kinds of trips: a couple’s outing during a Williamsburg vacation, a family activity for visiting relatives, a corporate team-building afternoon, or a hands-on introduction to sailing for someone who has never been on a sailboat before.

Guests who want a more active role on the water can ask about the Adventure Cruise or Lessons Cruise, both of which involve steering and handling the boat under the captain’s guidance. Those planning a special occasion can look at the Event Cruise, while history-focused travelers may prefer the History Cruise for its focus on the naval battles that took place along this stretch of the York River.

Reservations for Williamsburg Charter Sails can be made directly for a preferred date and charter type, with departure times set daily at 11:00 a.m. and 2:30 p.m. throughout the sailing season. Whether the goal is a relaxed couples’ sail, a family outing, a corporate retreat, or an introduction to sailing basics, Williamsburg Charter Sails structures each of its six charter types around a specific kind of experience on the York River.