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  First of all, it was my wife’s birthday on the Tuesday after Thanksgiving, November 29 so we called on November 28 not realizing that Bill had closed for the season... read more

    avatar thumb jamesoJ4648TX
    December 23, 2022
  • star rating  This was our first time sailing and my soon-to-be 21-year-old son and I had an incredible sailing experience with Captain Bill. The water was calm and peaceful, and the weather... read more

    avatar thumb N3-2022
    November 13, 2022
  • star rating  A sail with Williamsburg Charter Sails was a surprise for my husband’s birthday. The boat is a beautiful 32 footer that is kept in tip top shape. Captain Bill gave... read more

    avatar thumb Mona O
    November 9, 2022
  • star rating  My husband and I enjoy battlefields and history but wanted a slightly different way to experience the area than visiting a national park. Williamsburg Charter Sails was the perfect balance... read more

    avatar thumb LostPassport434
    October 29, 2022
  • star rating  Sailing Adventure - We had a lovely time. Capt. Bill was a great guide and my husband thoroughly enjoyed sailing the boat.

    October 29, 2022
  • star rating  We spent our 10th anniversary in Williamsburg and capped off our trip with a day of sailing. It was a gorgeous day, with both beautiful views and temperatures. We even... read more

    avatar thumb jessica4746
    October 24, 2022
  • star rating  Super Saturday Sailing - Captain Bill was a great historian. We took the afternoon historic sail. He was very infromative and entertaining. It was a great way to spend a fall... read more

    Pam M
    October 24, 2022
  • star rating  Wonderful Day Sail - Great Day Sail with Captain Bill. Very well organized trip, lovely boat and marina. We appreciated the updated weather forecast and the instructions received prior to departure. We enjoyed... read more

    Jennifer P
    October 24, 2022
  • star rating  What an incredible experience my wife and I had on our 32nd wedding anniversary. What a beautiful and extremely well maintained boat and Captain Bill was a very experienced and... read more

    avatar thumb jefvet
    October 23, 2022
  • star rating  Exceeded all expectations! - Our afternoon of sailing for my husband's birthday exceeded all expectations! Captain Bill was so easy to work with and communicative in scheduling from the start. Once we... read more

    October 21, 2022