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Sail Yorktown

Yorktown's Sailing Tours: Yorktown, VA

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Explore Yorktown's Sailing Charters

Explore Our Yorktown Sailing Charters

Yorktown Sailing Charters | Williamsburg Sailing

Set Sail for a By-Gone Era with Yorktown Sailing Charters

Step back into history when you join the crew of the Yorktown Schooner Alliance or Schooner Serenity. Lend a hand at setting sail, take the helm and steer the ship, or look for dolphins and osprey as you glide along the shores of the York River. You will relive sailing’s Golden Age as you cruise past the Victory Monument and Battlefield where our country won its independence. Book your Yorktown cruises online today!

For those who love history, yearn for romance, or have dreamed of a true sailing adventure,

Your Yorktown Ship has just come in!

Setting sail on the historic waters of Yorktown, VA is a magical experience. Let yourself fall into the rich surrounding history and the majestic ship you’re aboard while amongst family and friends – a fresh breeze pulling it all together. It’s our passion at Yorktown Sailing Charters to introduce you to the beauty of the waters we’ve been sailing for over 30 years, give you lifelong memories and keep you coming back for more.

Whether you’re looking for things to do in Williamsburg, VA or searching among the best sailing charters on the Chesapeake Bay, your journey stops with us.

a group of people on a boat in a body of water

Yorktown Cruises & Sailing Specials

Special events are welcome as we are pleased to offer private sailing charters for weddings, corporate cruises, our own exciting pirate cruises and more. Among the popular pirate cruises you will watch as the kids raise the sails, learn sailors skills and truly experience what it was like years ago aboard a schooner! Catering services and beverages for purchase are available options for your convenience.

For the ultimate enjoyment of a day of sailing come join Yorktown Sailing Charters. After boarding the Schooner Alliance II (48 passengers max) or Schooner Serenity (6 passengers max) you will understand why so many satisfied customers have raved about our sailing cruises for years! We look forward to introducing you to the history, romance and beauty found in and around our boats.

Yorktown Cruise Ships & Sailing Charters Events

Thank you for checking out our website. Continue browsing around for more information on our Chesapeake Bay and Yorktown, VA sailing and boat tours. If you have questions about any of our tours or how you can book a tour, give us a call today at 888-316-6422 or send an email. We look forward to hearing from you and taking you on your next sailing tour!

What Our Customers Have To Say!


Delightful Sail!

A wonderful afternoon with friends sailing out of Yorktown. It was a delightful 90 minutes on the water aboard a two-masted schooner.

– Doug H ● Tripadvisor

Great Experience!

It was our first time visiting Williamsburg Yorktown and Jamestown and the sightseeing sail was definitely something we wanted to do and we were not disappointed. The Captain and crew were very friendly and we learned a lot of history of the area. Overall it was a wonderful time and very relaxing afternoon. Would definitely recommend!

– Jen G ● Tripadvisor

Yorktown Sailing Charter!

We had a great time. Wish there would have been a little more wind. The commentator was very well versed in his local history.

– K9502WFjay ● Tripadvisor

We had a blast!

We thoroughly enjoyed our sunset cruise. The crew was excellent and we especially enjoyed the history lesson. We highly recommend Yorktown Sailing Charters.

– Debra L ● Tripadvisor


It was very informative and fun. Would do it was not crowded like other tours. The crew was very friendly. You definitely get what you pay for.

– marshanwatts ● Tripadvisor