Let's Go Sail.
Join Us for Private or Group Cruises, Daily Charters and Lessons Along the York River
757-876-8654 or bodonovan8@gmail.com
Reviews
- Dustin V
We had 6 of us, my wife and I and our 4 kids ages 18,17,13,and 10. We all had a great time it was very relaxing on the water... read more
August 20, 2023
Charters
Choose from 6 Unique Sailing Charters
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.
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.)
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.
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.
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.
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.
Rates
3-hour cruise departs daily at 11:00 and 2:30
Couples
Semi-private
- $150
- Perfect for couples or friends
- 3 hours sailing charter on York River
- Cold bottled water provided, food welcome
- Boat may include up to two other couples
MonMake Your Reservation by EMAIL
Let's Go Sail! Williamsburg Charter Sails departs twice daily April - November for skippered cruises.
Reservations are first-come, first-reserved. No booking fee, Visa and MasterCard accepted.
Complete the reservation form below. You'll receive an email confirmation when your trip is secured.15-Day Availability
Saturday
Sept 2311:00am Washout 2:30pm Washout Sunday
Sept 2411:00am Sold Out 2:30pm 2 OPEN Monday
Sept 2511:00am2 6 OPEN 2:30pm 6 OPEN Tuesday
Sept 2611:00am 6 OPEN 2:30pm 6 OPEN Wednesday
Sept 2711:00am 6 OPEN 2:30pm 4 OPEN Thursday
Sept 2811:00am 6 OPEN 2:30pm 6 OPEN Friday
Sept 2911:00am 6 OPEN 2:30pm 6 OPEN Saturday
Sept 3011:00am6 Sold Out 2:30pm 6 OPEN Sunday
Oct 111:00am 6 OPEN 2:30pm 6 OPEN Monday
Oct 211:00am 6 OPEN 2:30 pm 6 OPEN Tuesday
Oct 311:00am 6 OPEN 2:30 pm 6 OPEN Wednesday
Oct 411:00am 6 OPEN 2:30 pm 6 OPEN Thursday
Oct 511:00am 6 OPEN 2:30 pm 6 OPEN Friday
Oct 611:00am4 6 OPEN 2:30 pm 6 OPEN Saturday
Oct 711:00am 6 OPEN 2:30 pm Sold Out
FAQ
Email bodonovan8@gmail.com and you'll get a prompt reply.You’ll enjoy 3 hours of safe and comfortable sailing on a modern single-mast sailboat. An optional short narrative outlines the decisive battle of the Revolutionary War.Along the York River, off historic Yorktown.Drive south from Williamsburg on the Colonial Parkway for 15 minutes.Check out the Captain's Blog rail on this website to see how people enjoy great fun and conversation with our luxury sailboat charter, in a safe and unique setting. Call up Williamsburg Charter Sails on Facebook for photos and stories.Come as family or your own private group of up to six people.Yes, we welcome one, two or three unrelated couples at $150 each.Yes. We'll send you the best shots for free so you can post or print them as you like.We typically sail at 11 and 2:30, but it depends on your schedule.A cooler with bottled water and ice is on board for your drinks, along with the full amenities of an appointed interior salon.Yes, a working head plus hot and cold water. There’s privacy to change into bathing suits.Bring a sweater and jacket in the fall.Yes, certified US Coast Guard PFDs are provided.Kids 12 and under can be problematic on a sailboat. They will have to wear life jackets regardless. It’s your call. Sorry, no. This is a family-friendly enterprise.At York River Yacht Haven marina, we can get a wheelchair within several feet of the transom to walk him or her on board, with no climbing. It's quick and easy.No, six maximum. Coast Guard regulations preclude any more, including children.Oh sure. Bottled water is provided too.We’ll try to reschedule your sailboat charter. Sometimes an afternoon shower interrupts a sail, but only briefly. If the trip is washed out, you won't be charged.They usually pop up in late afternoon, so an 11 a.m. departure is best.Request a day and time by calling 757 876-8654 or emailing bodonovan8@gmail.com. It's that easy.Certainly. Give us a shout.They are typically 5-15 mph, which is excellent.Then the sails are easily shortened or "reefed" to ensure comfort and safety for all while still retaining speed. Yes, heeling is one of the many joys of sailing because it connotes speed. But no more than 10 or 15 degrees, to ensure everyone's comfort. Anything beyond that is hot-dogging.Absolutely not. Nor would you be exposed to such conditions. Safety and comfort are paramount to enhancing the fun of our sailing charters.No, never. Safety is paramount.Yes, a bimini awning covers the back quarter of the cockpit.We form up in Yorktown or Gloucester Point, depending on various factors. See LOCATION tab for directions. Yorktown is at Riverwalk, while Gloucester Point hails York River Yacht Haven, 8901 York Haven Road.Yes, consider us a sailing vacation from the every day. Executive team-building, class reunions, wedding parties, even burials at sea are all welcome.Seven days a week, from mid-April to mid-November.It's highly unlikely, since the waves on an inland river are much gentler than those found on the Chesapeake Bay or Atlantic Ocean. For those in doubt, take Dramamine the night before to get it fully into your system. We also have motion sickness wristbands and ginger gum on board.
About
Meet Your Captain
Bill O’Donovan holds a 50-ton captain’s license with the US Coast Guard. Need sailing lessons? He is a certified sailing instructor with the American Sailing Association. He has undergone sailing instruction by J School in Key West and by the American Sailing Association in South Carolina. He has sailed the York River nearly 20 years, where he teaches an adult class for the community-based Williamsburg Area Learning Tree.
Our Fleet
When you join us for your sailboat charter, you’ll sail on a 32-foot modern Hunter complete with in-mast furling and oversized sails for maximum speed. Sophisticated controls reduce the size of the sails to minimize leaning and ensure everyone’s comfort. A giant colorful spinnaker is raised for light downwind running. Yanmar 18 horsepower diesel powers the boat in creeks.
With sailing instruction through our sailing school you'll learn what will enable you to sail most any boat. The boat meets all US Coast Guard standards and has shipshape equipment, including color-coordinated lines and well-marked blocks.
With our many charter sailing options, we have the right tour whether you're visiting our area from out of town and in search of a unique vacation adventure, an employer wanting the perfect corporate retreat or a local looking for a fun family chartered sailboat trip.
Press
Original Article-The Local Scoop "Williamsburg By Sea"
“ The tranquility of being on the water, the rush of being propelled by the wind, and the joy of gliding over the waves alongside dolphins—those are just a few of the reasons why Bill O’Donovan enjoys sailing.
“It’s the idea of being on the water,” O’Donovan says. “There’s something about that that’s magical. There’s a certain solitude to it.”
Location
We Sail Across from Yorktown
Take the Coleman Bridge across from Yorktown to York River Yacht Haven at Gloucester Point. Follow the map for 17 miles from Williamsburg. For GPS directions, type in “York River Yacht Haven.” View York River Yacht Haven DirectionsYork River Yacht Haven
