• 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


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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…


Sailing Big

The Sefcik family of Ringoes, New Jersey, went sailing near Williamsburg while in town showing…



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…