Choose from 6 Unique Sailing Charters


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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

Adventure, Birthday, Boat Buying, Charter sail, Dolphins, Family, Flying, How to, Navy, Rates, Rescue, Sailing, Spinnaker, Trip Advisor, Williamsburg, York River

Sailing at 85

  A Maryland family rescheduled a rain date and wound up sailing the York in a rising afternoon breeze that they found a magnificent adventure. Weeks earlier, Kathy Self had hoped to bring her uncle along with her father Jack Green as a birthday surprise on their 85th. “In retrospect this worked out better,” she said, “as he’s cranky and would have resisted the sailing. Dad loves this.” Jack is retired from a long career in graphics and printing in Washington. Kathy is finishing up…

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…