Step aboard a classic two-masted schooner and feel Yorktown’s storied past come alive on the breeze. For more than 30 years, the family-run Yorktown Sailing Charters crew has shared these historic waters with guests, pairing authe...
Sailing with this crew is consistently described as a highlight of visiting the Yorktown area. The captains and staff earn overwhelming praise for being friendly, knowledgeable, and genuinely engaging. Passengers appreciate the historical narration that brings the York River and surrounding area to life, with crew members like Darby getting specific shoutouts for their storytelling abilities. The fleet includes schooners like the Alliance II and Serenity, offering everything from pirate-themed adventures for kids to romantic sunset cruises. The experience strikes a nice balance between relaxation and activity. Many guests mention getting hands-on opportunities to help raise sails, spotting dolphins, and enjoying the surprisingly comfortable conditions even on hot days thanks to shade from the sails. Light snacks are available at reasonable prices. Repeat visitors note that quality has remained excellent even through ownership changes, with families returning year after year for different cruise options. Whether you're looking for educational value, a special celebration, or simply a beautiful way to spend an afternoon on the water, the crew makes sure everyone has a memorable time.
There is nothing like sharing a picnic on a pirate ship. We gad such a great experience aboard the Alliance Schooner. A special thank you to the captain and his staff for helping to make our trip very memorable and enjoyable. We have done all of the different trips with them over the years and I can definitely say we have never been disappointed. Why go anywhere else when we can vacation in our own backyard. Williamsburg, Yorktown and Jamestown has so much to offer. Thank you again for making this day special.
June Yuiska
September 4, 2025
There is nothing like sharing a picnic on a pirate ship. We gad such a great experience aboard the Alliance Schooner. A special thank you to the captain and his staff for helping to make our trip very memorable and enjoyable. We have done all of the different trips with them over the years and I can definitely say we have never been disappointed. Why go anywhere else when we can vacation in our own backyard. Williamsburg, Yorktown and Jamestown has so much to offer. Thank you again for making this day special.
June Yuiska
September 4, 2025
