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Williamsburg Charter Sails

Williamsburg Charter Sails is dog-friendly. They offer six different types of cruise and welcome Fido to join you on board for no extra fee. Their most popular sailboat charter lets you relax as you feel the wind in your hair or become a member of the crew. While on the water, you can navigate the York River and take in 200 years of history that links Yorktown with Williamsburg and beyond to the Chesapeake Bay. Captain Bill, the owner, keeps his family rate at $250 for up to six people to encourage everybody to get their sea legs and turn Fido into a sea dog. Visit Website

Or call (757) 876-8654 for more information.


BringFido Guest Rating
TripAdvisor Traveler Rating

Williamsburg Charter Sails has received a rating of 5.0 out of 5 bones by 5 canine critics on BringFido and 5.0 out of 5 by 604 guests on TripAdvisor.

  • Sep. 21, 2022
    Captain Bill is the best in the York River!

    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! We decided to take the historical tour, and Captain Bill was a great Naval Battle guide. In our three hours, he let two of us take the wheel. I got to spend some time at the bow of the boat. Our pup loved the smells of the ocean and Captain Bill was great with him. We would 100% recommend this trip for any families with a pup!

  • Rick
    Jul. 22, 2021
    Captain Bill Rules The Chesapeake Bay

    Best way to see the bay and enjoy the scenery ... Captain Bill is informative as to the area and entertaining My pooch (Rigatoni) loved the ride If you do nothing else in Williamsburg take this ride...5 bone rating is not enough We give it a 10

  • Kenneth
    Jun. 21, 2021
    Enjoy the York with your Pups!

    It was such an enjoyable afternoon and a great way to see the area. I learned a lot - and thank Captain Bill for the opportunity to helm. The boat is well maintained and professional. The best part - Captain Bill allows dogs and they had a great day on the river too!

  • L
    Oct. 16, 2019
    Wonderful time!

    We would sail with Captain Bill again in a heartbeat! Our family of 5 to include our 2 dogs (a toy breed and a medium sized mixed breed) had such a wonderful time. Captain Bill is very friendly and ensured that we all had a great time — including our pups. He had a rug out so they could feel safe and stable and let us borrow a rope to tie our leash so we wouldn’t have to hold onto it and truly be able to enjoy the sail. The boat is beautiful and clean and we were thrilled to be able to participate in steering and hoisting the sails. Williamsburg Charter Sails is one of the few excursions where you can enjoy with your whole family and pups — highly recommended!

  • Ranger
    Sep. 24, 2018
    Amazing trip !!!

    We had a wonderful time cruising with Captain Bill. It was the highlight of our vacation. Our 2 year ago rescue, Ranger (boxer/lab mix), loved being on the sailboat and Captain Bill treated him like a king. He provided Ranger with water and a rug to lay on but Ranger was very happy just sitting on Captain Bill's lap while my husband sailed the boat (with Captain Bill's guidance of course). Our kids had a great time too! Captain Bill is extremely knowledgeable about the area and pointed out many sites that we would not have been able to see from the land.
    It's is well worth the money... treat yourself, your family and your favor "Fido" to a great sailing experience!!!!

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We dug up 4 pictures of dogs at Williamsburg Charter Sails.

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Williamsburg Charter Sails