• star rating  This was one of the highlights of our week-long trip to the Williamsburg, VA area! My family opted to set sail with Captain Bill because my kids are too old... read more

    May 27, 2022
  • star rating  This was a wonderful surprise birthday gift! Bill invited us to take the helm, help with sails while he pointed out points of interest on the beautiful, wide York River.

    May 22, 2022
  • star rating  Captain Bill provided a great sailing experience along with educational nuggets about the Yorktown area. A very capable and knowledgeable captain who took good care of his “crew”. Recommend you... read more

    May 14, 2022
  • star rating  While most people would have thought we were crazy to go sailing on a cloudy and windy day, it was actually a great day to be out on the water... read more

    May 13, 2022
  • star rating  We loved our cruise. Wish we could have stayed longer and done two back to back! Captain Bill was very knowledgeable and the boat was beautiful! Definitely recommended!

    May 12, 2022
  • star rating  Our three hours sailing with Captain Bill was the highlight of our vacation, something we will never forget. Really the best way to see Tidewater.

    May 7, 2022
  • star rating  We had a wonderful time on this sail. Captain Bill was pleasant and knowledgeable about sailing and the river. The boat was immaculate.

    May 3, 2022
  • star rating  Captain Bill offered a unique hands-on sailing experience on the York River during our trip on 4/28/22 afternoon cruise. The variable winds and the air temperature were brisk which kept... read more

    April 29, 2022
  • star rating  Captain Bill provided us with an excellent sailing experience. We had a wonderful time. I and my husband really enjoyed the teaching of how to steer the helm and the... read more

    April 26, 2022
  • star rating  Great way for a family to spend 3 hours relaxing on the water taking in the sites. Bill knows his sailing and area history. He was a lot of fun... read more

    April 25, 2022


Choose from 6 Unique Sailing Charters


3-hour cruise departs daily at 11:00 and 2:30

  • Couples


  • $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
  • Families


  • $250
  • Up to six people
  • 3 hours sailing charter on York River
  • Kids 12 yrs+ recommended
  • Cold bottled water provided, food welcome
  • Groups
  • $350
  • Up to six people
  • 3 hours sailing charter on York River
  • Sailing lesson optional
  • Cold bottled water provided, food welcome


Make 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.
* indicates required field

15-Day Availability

May 29
11:00am2sold out
2:30pmsold out
May 30
11:00amsold out
2:30pmsold out
May 31
11:00am6 OPEN
2:30pmsold out
June 1
11:00amsold out
2:30pmsold out
June 2
11:00am 4 OPEN
2:30pm6 OPEN
June 3
11:00am6 OPEN
2:30pm6 OPEN
June 4
11:00amsold out
2:30pm6 OPEN
June 5
11:00am3 OPEN
2:30pm6 OPEN
June 6
11:00am36 OPEN
2:30pm42 OPEN
June 7
11:00am6 OPEN
2:30 pm6 OPEN
June 8
11:00am6 OPEN
2:30 pm3 OPEN
June 9
11:00am6 OPEN
2:30 pm6 OPEN
June 10
11:00am2 OPEN
2:30 pm6 OPEN
June 11
11:00am4 OPEN
2:30 pmsold out
June 12
11:00am6 OPEN
2:30 pm6 OPEN


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.

  1. Safe and comfortable 3 hours

  2. Adult sports adventure

  3. "Sail About" fun at 11 & 2:30

  4. Full bathroom on board

  5. Unique family adventure

  6. Check off your bucket list

  7. Great for special occasions

  8. Enjoy nature & sightseeing

  9. Take short sailing lessons

  10. Buying a boat? Try this first

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.


Meet Your Captain

Captain Bill
coast guard licenseBill 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.


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.”

Read More


We Sail Across from Yorktown

York River Yacht Haven

York River Yacht Heaven

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 Directions

York River Yacht Haven