Yorktown Pirate Adventure Sail

Join a kid-friendly schooner cruise to hoist sails, fire the cannon, and earn your pirate stripes

From$48/ person

Duration

1.5 hrs

Includes

Schooner cruise, Pirate activities

Highlights

Set sail aboard a historic schooner for a lively pirate-themed cruise on the York River. Kids become the crew as they raise sails, steer the helm, and learn seafaring skills while adults relax and enjoy the view.

Hoist the sails alongside the crew for wind-powered fun
Steer the schooner under the captain's guidance
Learn essential sailor knots and maritime skills
Show off temporary pirate tattoos for great photos
Hear the boom of the ship's cannon across the water

What's Included

1.5-hour schooner sail on the York River
Interactive pirate activities for kids
Use of life jackets and safety gear

Things to know

Cruise operates May through September and select spring break dates. Wear flat-soled shoes and bring a jacket in cooler weather. No outside food, coolers, or large items allowed aboard.

Cancellation policy

No refunds except for captain-determined weather cancellations. If a sailing is cancelled due to weather you will be offered to reschedule, receive a gift certificate, or obtain a refund. No-shows and late arrivals receive no refund.

Experience provided by Yorktown Sailing Charters

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Best local prices
Flexible cancellation
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Each booking directly supports small businesses in our community.

Yorktown Pirate Adventure Sail

Join a kid-friendly schooner cruise to hoist sails, fire the cannon, and earn your pirate stripes

From$48/ person

Duration

1.5 hrs

Includes

Schooner cruise, Pirate activities

Highlights

Hoist the sails alongside the crew for wind-powered fun
Steer the schooner under the captain's guidance
Learn essential sailor knots and maritime skills
Show off temporary pirate tattoos for great photos
Hear the boom of the ship's cannon across the water

What's Included

1.5-hour schooner sail on the York River
Interactive pirate activities for kids
Use of life jackets and safety gear

Things to know

Cruise operates May through September and select spring break dates. Wear flat-soled shoes and bring a jacket in cooler weather. No outside food, coolers, or large items allowed aboard.

Cancellation policy

Review summary

4.8

Excellent

460 reviewsGoogle Maps

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.

What people are saying

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.