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Reviews

  •   Requested and got a lesson while enjoying a wonderful many mile-covered 3-hour sail. Enjoyed the time; talked; asked questions; and got demonstrations. It was a day just prior to a front passage with lots of wind and some delightful heeling under close-hauled runs. I asked...More

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    11/07/2018
  •   Capt. Bill was a true professional who made everyone feel comfortable, safe and secure while teaching a bit of sailing infused with his history cruise package. Capt. Bill was the perfect example of the hospitality found within the sailing community. This day was much needed....More

    thumb Kevin A
    11/07/2018
  •   We greatly enjoyed our sailing trip on the York River. Bill was a knowledgeable and personable captain, and offered both saing advice and historical narrative about the battles of Yorktown during the three hour tour.

    thumb Benjamin S
    11/04/2018
  •   Capt Bill took such great care of my three boys. Every detail was attended to, and he taught them not only about the local history, but also how to sail! He instinctively knew what each boy needed, and provided it. He's got to be the...More

    thumb TrippNC
    10/23/2018
  •   As part of a "Best of Virginia Tour" that we planned for Sailing friends of ours from Michigan, we scheduled a private charter with Williamsburg Charter Sails. Bill O'Donovan gave us 3 hours of fun, wonderful sailing, and a nice bit of history. The experience...More

    thumb Diana A
    10/23/2018
  •   We had an amazing time sailing for my husband birthday. Bill is an amazing captain. He’s very knowledgeable, comical and patient. The boat was clean and in good condition.

    thumb Ryan4lyfe
    10/20/2018
  •   Captain Bill did a great job. This was our first time sailing and he explained everything we needed to know in a manner we could understand. He even let us drive the ship and explained the best way to do so. I would recommend this...More

    thumb katekdg2018
    10/19/2018
  •   We went on an afternoon sail with a party of six, ages 9 to 78. Even though the wind did not always cooperate, Captain Bill turned this into a rather memorable experience for our kids and taught them the first basics of sailing, they both...More

    thumb mwkonig
    10/15/2018
  •   What a fun experience! It was my first time sailing and Capt Bill was so welcoming and easy going. If you want to have a blast and not expend much effort this is what you need in your life. Loved it <3

    thumb Cjwoodson
    10/07/2018
  •   Capt Bill is a great skipper and very knowledgeable on local history. Sailing was very enjoyable and wife loved the boat and river cruise. Would Highly recommend if in area that time to book this adventurer. Capt Bill will even give sailing tips and explain...More

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    10/06/2018

Charters

Choose from 6 Unique Sailing Charters

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
  • Families

    Family

  • $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

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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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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.



  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.

About

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.

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.”

Read More

Location

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