• Let's Go Sail.

    Join Us for Private or Group Cruises, Daily Charters and Lessons Along the York River


Choose from 6 Unique Sailing Charters


View all testimonials


Call 757 876-8654 for Availability

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

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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Captain’s Blog

Chesapeake Bay

Angry Bay

  Outside Deltaville, a churning Chesapeake Bay was smashing waves up to three feet against…



SAIL AVAILS – 757-876-8654 Sun May 1 – 11 am sold out, 2:30 RAIN Mon…


A Great Sailing Day

Debbie Black and her boyfriend Bernie Thomas drove from Frederick, Maryland, through terrible traffic on…


Sail Caymans

  Grand Cayman Island is a great place to sail — catamarans. Sloops with keels…


No Flags Today

Nor’easter winds are expected to gust 30-40 mph this weekend atop the renamed American Revolution…


Sailing Cold

  Fred and Barbara Johnson live in Ely, Minnesota, close to the Canadian border. While…


Wounded Bird

This double-crested Cormorant was walking slowly on the bulkhead of York River Yacht Haven, apparently…


Sailing Free

Carol Roehling took her husband Alex Shalash’s family sailing in brisk winds on the York…


Birthday Sail

Larry Perlow’s children sent him sailing with a pal on the York River. In retirement,…


Sailing Later

Linda Louise Stamper of Indianapolis and her beau Scott dated a few times in high…


Sailing Redux

Melanie and Horace Gilchrest of Portsmouth took their three sons on Willoughby Bay aboard SailTime’s…


Sailing past Hugo

Hurricane Hugo devastated Charleston in 1989, leaving thousands without homes and power for weeks. Karen…


Sailing to Tortola

Here’s an added feature to home-schooling. Every winter Lori and Jason Eitel of Conifer, Colorado,…


Sailing to Sports

Sheila and Russ Abelein of Long Island raised their children to play competitive sports, including…


Sailing Small

It’s difficult to sail a small dinghy of 8 feet because it lacks maneuverability and…


Rescue at Sea

Those orange rescue vessels found on each side of merchant ship were made famous in…

How to

Colorado Sailors

Linda and Bill Schmidt of Westminster, Colorado, had a blast sailing the York River as…


By the bus

Nan Gillis of Tacoma, Washington, sailed on the York with a mixed experience of negotiating…



Stan Myers and Laura Brun sailed the York under a steady breeze in quiet solitude….


Birthday Sail

Drew O’Neal’s family threw him a wonderful birthday party while sailing all afternoon on the…


Beware the Navy

Pam Martin took Tony Telesmanic out for an early evening sail. She raises show horses…


Fast Pitch

Kristi Olsen and a contingent of York County tourism officials sailed Wednesday. Brian Fuller of…


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.


We Sail Out of Two Marinas

Riverwalk Landing, Yorktown

Riverwalk Landing, Yorktown VA

The first is Riverwalk Landing in revived Yorktown, where the docks are a few steps away from an enclosed garage offering free parking. Take the Colonial Parkway from Williamsburg for 15 miles to the Route 238 exit and follow the signs into town. We’ll meet at the Gazebo of the docks. For GPS directions, type in “Riverwalk Landing, Yorktown.”
Riverwalk Landing Marina

York River Yacht Haven

York River Yacht Heaven

The second location is York River Yacht Haven, at Gloucester Point on the north shore of the York River. This is preferred for those driving south from Fredericksburg on Route 17. Follow the map for 17 miles from Williamsburg. For GPS directions, type in “York River Yacht Haven.”

View York River