Welcome to Yorktown Sailing Charters!

Set Sail for a By-Gone Era

Step back into history when you join the crew of the Yorktown Schooners Alliance and 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 sailings Golden Age as you cruise past the Victory Monument and Battlefield where are country won its independence.

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

Your Ship has just come in!

Setting sail on the beautiful, sparkling 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 in Yorktown, your journey stops with us. Our impressive vessels include the Schooner Alliance and the Schooner Serenity. The Alliance is a historic wonder sailing in Yorktown for the summer and gracing the Caribbean in the winter. The Serenity, too, has a regal build offering you the chance to partake in one of our Chesapeake Bay cruises, learning history of pirates on the Bay.

All occasions are welcome as we are pleased to set sail as private sailing charters for weddings, corporate cruises, our own exciting pirate cruises and more. Among the popular pirate cruises you will hear local pirate stories, learn wisdom of sailors and truly experience what it was like years ago aboard a schooner! Food and beverages are conveniently available for purchase aboard the ship completing your day out on the water.

For the ultimate enjoyment of a day of sailing out on our pristine waters, join Yorktown Sailing Charters. After boarding the Alliance or the Serenity you’ll 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.

Chesapeake Bay Cruise Specials at Yorktown Sailing Charters
Thank you for stopping by and checking out our website. Continue browsing around for more information on our Chesapeake Bay and Yorktown, VA sailing and boat tours. In addition to these sailing charters, you will also find information on our Caribbean Islands winter week charters. If you have questions about any of our tours or how you can book a tour, give us a call today at 757-639-1233 or send an email to info@sailyorktown.com. We look forward to hearing from you and taking you on your next sailing tour!