Adventure Cruise

Adventure Cruise

30-Year-Old Sailor
Sailing Off Brazil
Captain's Choice
Sailing All Over America
Sailing from Rural America
Sailing Serenely

Our most popular sailboat charter lets you exhale and relax as you feel the wind in your hair.

Grab the wheel to become a member of the crew. Or sit back and enjoy the tranquility of nature’s silence, where the only sound is lapping waves.

Take in the thrill of moving with the wind without a care in the world. Take a sailing vacation, navigating the York River across 200 years of history that links Yorktown with Williamsburg and beyond to the Chesapeake Bay. 

Visiting from out of town? This cruise is a unique vacation adventure for all and a must do when visiting Williamsburg, Yorktown or the Greater Hampton Roads area. 

Tell us your sailing story to become part of a growing conversation about lessons learned from life, on and off the water.

Call 757 876-8654 for Availability

3-hour cruise departs daily at 11:00 and 2:30

  • Individual


  • $75
  • Meet Sailing
  • 3 hours sailing charter on York River
  • Kids 12 yrs+ recommended
  • Cold bottled water provided, food welcome
  • 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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  • star rating  We had a wonderful afternoon sail with Captain Bill on Sunday. He provides a really great introduction to the sport.

    June 22, 2022
  • star rating  We had a wonderful experience with Captain Bill. He was very knowledgeable of the York river and its history as well as the history of the battle of Yorktown. Will... read more

    Elizabeth W
    June 21, 2022
  • star rating  Wonderful sailing adventure on a pristine boat under the expert guidance of Capt. Bill. We received this experience as a Christmas gift from our son and daughter-in-law. It was a... read more

    June 21, 2022
  • star rating  You can make sailing with Captain Bill what you want: A private time. A sailing lesson. Good invigorating conversation. Party time. Renew relationships. Or a time-out from the noise of... read more

    June 19, 2022
  • star rating  Captain Bill was amazing! His knowledge, history, experience and safety protocols were impressive and very much appreciated! Lori B. and I are looking forward to the next sail already!

    June 15, 2022
  • star rating  Absolutely terrific experience. Captain Bill made us feel welcome and let me take the helm several times. For me the highlight was my second spell, when we had more wind... read more

    June 12, 2022
  • star rating  We (6 of us) had the best time sailing with Captain Bill. He was extremely accommodating telling us interesting things about the area and letting us do a lot... read more

    June 11, 2022
  • star rating  My wife and I recently took our friends from Florida for a sailing excursion with Williamsburg Charter Sails. We had perfect weather for a beautiful day of sailing on the... read more

    June 8, 2022
  • star rating  Thank you so much for a fantastic sail. We thoroughly enjoyed the relaxing adventure on a beautiful day with fun passengers & an awesome Captain!!
    Thanks for the pictures.

    June 8, 2022
  • star rating  Great opportunity to set sail on the river and chill. Captain Bill taught us how to catch wind in the sails and pretty much let us handle the vessel... read more

    June 6, 2022