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 6 of us, my wife and I and our 4 kids ages 18,17,13,and 10. We all had a great time it was very relaxing on the water... read more

    Dustin V
    August 20, 2023
  • star rating  Great time! - We were out in Williamsburg for our anniversary and decided to do a sail! Captain Bill was very nice and knowledgeable. He let us get involved- My husband helped with... read more

    August 15, 2023
  • star rating  Family Fun Sailing on the York River - Our family of four enjoyed our time out on the water sailing with Capt. Bill. We learned about steering the boat and each us were given the opportunity to take... read more

    August 15, 2023
  • star rating  Sailing with Dolphins - What an awesome day with Captain Bill of Williamsburg Charter Sails. Our family enjoyed sailing the York River as my dad did growing up. It was a beautiful day to... read more

    Amy H
    August 14, 2023
  • star rating  Excellent experience! - The captain was very knowledgeable about the history surrounding the river and the sea. He provides visuals and markers along the way. You can relax and enjoy the view and... read more

    August 11, 2023
  • star rating  A great day on the water. - Captain Bill was amazing in that he allowed us to sail his boat and had numerous stories of Navy ships that docked near the bridge. He was also encouraging... read more

    August 10, 2023
  • star rating  Bill is a great host and sailing captain. He welcomed us aboard and made us feel at home, allowing three of us to do most of the steering at... read more

    August 9, 2023
  • star rating  Great experience! - What a great day on the water! Captain Bill made us feel at ease as first-time sailors and allowed us to take the wheel for most of the trip. He... read more

    August 8, 2023
  • star rating  Enjoy a few hours at the speed of the wind - If you have been dreaming of turning off your phone for three hours, slowing down, taking a deep breath, and being present with friends and nature. Sailing with Captain... read more

    August 7, 2023
  • star rating  Great Experience - During our recent visit to Williamsburg we scheduled a 3 hour sailing tour of the York River with Captain Bill. It was a wonderful experience. Beautiful day for... read more

    August 6, 2023