Let's Go Sail

For the finest Outdoor Activity near Williamsburg, let’s go sail the ultimate Boat Tour on the majestic York River. Couples and families enjoy a highly Popular Experience for visitors and locals alike.

  • 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 and capitan Bill is very informative. He had some great information and allowed all the kids to spend time at the wheel, which they all loved as well. They all wanted to go again and wanted to get a boat after the fun day they had on the water.

    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 the sails, and I got to steer the boat! It was a good time with good conversation. Unfortunately, we didn’t have a lot of wind that day, so we didn’t get to “sail” much. Captain Bill refunded our money, even though he doesn’t control the wind. We were very appreciative of captain Bill taking us out on the water, and I would love to do it again!

    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 the helm and steer. The outing was very relaxing and something fun to do with our boys. Thanks, Capt. Bill!

    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 share and honor memories of time spent with him while on the water. Seeing the dolphins and sailing alongside of them made the day. We highly recommend spending the day with Captain Bill. He is a fun, knowledgeable, and friendly captain and host.

    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 also learn a little about sailing and the boat! I even got to captain the boat for a little while. The captain was very accommodating and considerate. Not to mention that pictures from the trip are included in the voyage. I would highly recommend this experience as it is much more personable than a typical cruise/voyage. The restaurant was also VERY good and I appreciate the captains recommendation.

    August 11, 2023

Choose from 6 Unique Sailing Charters

Adventure Cruise

Our most popular sailboat charter

Grab the wheel to become a member of the crew.

Event Cruise

A panoramic backdrop to your event

A unique way to celebrate an anniversary, birthday, proposal or other special event

Appreciation Cruise

Take your top staff on the ultimate retreat

Leave the cell phones behind to focus on gratitude for their work

History Cruise

Our area is steeped in history

see the 1781 Battle of the Capes and the Battle of Yorktown from the York River

Lessons Cruise

Sailing is fun and easy to learn

Take a short course through our sailing school to get oriented on the basics.

Boat Buyer Cruise

Looking to invest in a sailboat?

It’s the most fun you can ever imagine.

We Sail Across from Yorktown

Click on View Larger Marp and then Directions (under Overview). Type in your starting point, eg. Williamsburg. Take the Coleman Bridge across from Yorktown to York River Yacht Haven at Gloucester Point. Follow the map for 17 miles from Williamsburg. For GPS directions, type in “York River Yacht Haven.”