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  Once again we had a memorable time with Capt. Bill. The boat is impeccably maintained, the Captain experienced and very knowledgeable of the area, and the conditions were most... read more

    October 1, 2022
  • star rating  Captain Bill deserves the high marks - he was very flexible and understanding in helping accommodate an older family for a birthday sailing trip.

    September 28, 2022
  • star rating  Our 3 hour sail with Captain Bill surpassed our expectations. My husband, being an experienced sailor, got to take the helm. Turns out Capt. Bill is not only... read more

    September 22, 2022
  • star rating  We were looking for something we could do with my 4.5 month old puppy and my parents who have mobility restrictions. Captain Bill was able to accommodate everyone! ... read more

    September 21, 2022
  • star rating  Captain Bill is fantastic! He is very knowledgeable and fun. The boat is beautiful. We all had a terrific day sailing!

    September 16, 2022
  • star rating  The Captain was a great man with extensive knowledge of the area and extremely well familiar with the history of the area and specifically the Revolutionary War. His sailboat was... read more

    September 9, 2022
  • star rating  Capt Bill is a seasoned sailor and takes great care of his guests, Very enjoyable afternoon sail and learned many new things about sailing and the local area. Highly recommend

    September 6, 2022
  • star rating  Such a fun day on the water - Bill was so easygoing and let my family sail which meant so much! I would definitely recommend this to anyone who wants... read more

    August 16, 2022
  • star rating  Bill is a gentleman. My wife and I took our three college age kids and everyone had a great time. I highly recommend it.

    August 14, 2022
  • star rating  Wow beyond expectations and a great experience! Captain Bill came, saw, and delivered and amazing sail with much information along the way talk about my first time sailing ️... read more

    August 10, 2022