All Sailing Charters

Sail Yorktown with our Luxury Charters

Discover the joy of sailing in Yorktown, VA with Yorktown Sailing Charters. Join us for memorable sailing adventures on the Chesapeake Bay. Enjoy the beautiful Virginia sunset, a pirate-themed cruise, or private sail on our luxury charters. You never know what sea life you’ll encounter! Set sail and keep an eye out for dolphins and osprey. Sail by 18th Century homes and Naval warships or submarines with Yorktown Sailing Charters. Book online today!

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From $45

Schooner Alliance II
1 hour and 30 minutes
All ages

Schooner Alliance II: Yorktown Sightseeing Day Sail

Enjoy a daytime cruise aboard the Tall Ship Alliance II on the York River from the Riverwalk Landing Pier. Immerse yourself in 300 years of history and enjoy the village streets and paths overlooking the York River before you board the ship. Book online!

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$55

Schooner Alliance II
2 hours
All ages

Schooner Alliance II: Yorktown Scenic Sunset Sail

Take a scenic sunset cruise aboard the Tall Ship Alliance II on the York River from the Riverwalk Landing Pier. Come aboard and enjoy the evening views of the York River while enjoying a beverage from our ships’ galley.

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From $35

1 hour and 30 minutes
All ages

Yorktown Pirate Ship Adventure Sail

Bring the kids to Captain Mayhem’s School of Piracy and watch them set the sails, steer the schooner, and learn sailor skills! This sail is our kid-friendly cruise, recommended for kids 10 and under. Older kids may prefer Sightseeing Day sail.

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$75

July 4th Fireworks Cruise

What could be more patriotic than watching the July 4th Fireworks from a tall ship at Yorktown’s waterfront? This trip departs after the sunset sail and returns after the fireworks.

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