Choose from 6 Unique Sailing Charters

Adventure Cruise

Our most popular sailboat charter lets you exhale and relax as you feel the wind in your hair. Grab the wheel to become a member of the crew. Or sit back and enjoy the tranquility of nature’s silence, where the only sound is lapping waves. Take in the thrill of moving with the wind without a care in the world. Take a sailing vacation, navigating the York River across 200 years of history that links Yorktown with Williamsburg and beyond to the Chesapeake Bay. Visiting from out of town? This cruise is a unique vacation adventure for all and a must do when visiting Williamsburg, Yorktown or the Greater Hampton Roads area. Tell us your sailing story to become part of a growing conversation about lessons learned from life, on and off the water.

Stories from the Captain

Event Cruise

A sailboat charter is a unique way to celebrate an anniversary, birthday or other special event. The York River is also a panoramic backdrop for the once-in-a-lifetime opportunity to propose marriage on a sailboat, complete with a photographic record of popping the question. (Please say Yes.)

Stories from the Captain

Appreciation Cruise

Take your top staff on the ultimate retreat, a sailboat charter on the York River with intimacy and no distractions. Leave the cell phones behind to focus on gratitude for their work, as well as team-building for the future. A sailing vacation from the office offers a metaphor for timing, skills and decision-making. Learn how sailing helps coordinate vital activities, how to give directions well and how to reach the destination with confidence. That’s called leadership.

Stories from the Captain

History Cruise

Our area is steeped in history. Locals and visitors alike can experience this unique vacation adventure on our sailing charter and see the 1781 Battle of the Capes and the Battle of Yorktown from the waters of the York River. See where the French bottled up the York River to prevent a British rescue by sail fleet. Learn how Cornwallis failed to attack Washington in Williamsburg. Discover where the term “hot shot” derived and where the Purple Heart was founded. Plus: How Yorktown figured in the 1862 Battle of Williamsburg in the Civil War. A must do when visiting Williamsburg.

Stories from the Captain

Lessons Cruise

With sailing lessons from Williamsburg Charter Sails, sailing is fun and easy to learn, well within the reach of the average person. Take a short course through our sailing school to get oriented on the basics.

  • Learn boating safety.
  • Learn the aerodynamics of sailing.
  • Differentiate the three sail “reaches” for power.
  • Learn how to “see” the wind.
  • Find out how to rescue a man overboard quickly.
  • Try your hand (and voice) at marine radio.
  • Help deploy the spinnaker sail when going downwind.
  • Get the basics of preventative maintenance for diesel engines.
  • Follow up with ASA-sanctioned sailing lessons.
Stories from the Captain

Boat Buyer Cruise

Looking to invest in a sailboat? It’s the most fun you can ever imagine. To discourage joyriding, most sailboat brokerages require a signed contract for a test drive. Well, it’s a joy to test our 32-foot Hunter sloop, with all the amenities. Go through a checklist of what to look for when buying. Take a quick course in engine preventative maintenance, complete with checklist.

Stories from the Captain