• star rating  captain bill was a great host ! has great knowledge and we learned alot . its very worth the trip, you should book your trip now

    tim parker
    September 4, 2021
  • star rating  We were visiting the Williamsburg area for the week and knew we wanted to experience some sort of boat tour, and since neither of us had been sailing before, we... read more

    August 28, 2021
  • star rating  We had a fantastic time sailing with Captain Bill. He explained much about sailing--the wind, sails, and navigation--with gracious courtesy. His sailboat, the Deadline, was very comfortable and nice appointed.... read more

    August 25, 2021
  • star rating  You can sit back and soak in the the bay or, if interested, take the wheel and learn a little about sailing. Will do it again

    August 21, 2021
  • star rating  Captain Bill was easygoing and friendly. He knows quite a bit of the history of the area and gave good sailing tips as well.

    August 14, 2021
  • star rating  Fully satisfied and recommend to anyone without sailing experience seeking to get hands on experience as well as time out on water…….On my outing we saw Dolphins, and a... read more

    August 12, 2021
  • star rating  My first time sailing experience and Capt Bill was exceptionally congenial. His vast sailing experience became obvious from the start of leaving the slip and setting sail, he... read more

    Brendan R
    August 12, 2021
  • star rating  We celebrated our wedding anniversary and we had an amazing time. Capt Bill was very professional, knowledgeable and the boat was clean and we enjoyed the pictures with a... read more

    August 10, 2021
  • star rating  My son and I decided to take a sailing charter last minute…we are so grateful we found Captain Bill. He did an amazing job making us feel welcome, and gave... read more

    Jeanne M
    August 4, 2021
  • star rating  My family came for a girls trip and we had an awesome time. Captain was attentive and professional. We would definitely come back again!

    August 2, 2021


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.
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15-Day Availability

Sept 19
11:00am sold out
2:30pm sold out
Sept 20
11:00am 2 OPEN
2:30pm 6 OPEN
Sept 21
11:00am sold out
2:30pm 6 OPEN
Sept 22
11:00am sold out
2:30pm sold out
Sept 23
11:00am CLOSED
2:30pm FOR
Sept 24
11:00am ANNUAL
2:30pm FALL
Sept 25
11:00am REPAIRS
2:30pm AND
Sept 26
11:00am MAIN-
2:30pm TENANCE
Sept 27
11:00am CLOSED
2:30pm CLOSED
Sept 28
11:00am 6 OPEN
2:30 pm 6 OPEN
Sept 29
11:00am 6 OPEN
2:30 pm 6 OPEN
Sept 30
11:00am 6 OPEN
2:30 pm 6 OPEN
Oct 1
11:00am 6 OPEN
2:30 pm 6 OPEN
Oct 2
11:00am sold out
2:30 pm sold out
Oct 3
11:00am 6 OPEN
2:30 pm 6 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