Yorktown Sailing Charters has offered historic sailing tours on the York River for more than 30 years, giving visitors a chance to relive sailing’s Golden Age aboard the tall ship Schooner Alliance II or the more intimate Schooner Serenity. Departing from Riverwalk Landing Pier in Yorktown, Virginia, cruises pass the Victory Monument and Battlefield where American independence was won, with guests welcome to lend a hand setting sail or take the helm.
The most popular offering, the Sightseeing Day Sail, runs 90 minutes and immerses guests in 300 years of local history along the York River, starting from $61.42. The Scenic Sunset Sail runs 2 hours with evening views and a beverage from the ship’s galley, starting from $72.39. A kid-friendly Pirate Ship Adventure Sail (recommended for ages 10 and under) lets children set sails, steer the schooner, and learn sailor skills through “Captain Mayhem’s School of Piracy,” also starting from $61.42. A special July 4th Fireworks Cruise offers a rare vantage point for watching fireworks from a tall ship, with both individual tickets and a private 6-passenger charter option starting from $220.44.
The Schooner Alliance II holds up to 45 passengers, while the smaller Schooner Serenity accommodates up to 6, giving groups flexibility for private charters, weddings, corporate cruises, and other special events, with catering and beverage purchase options available. Guests consistently praise the crew’s deep local history knowledge and friendly, informative commentary throughout each cruise.
For anyone visiting Yorktown, Williamsburg, or Jamestown looking for a historic sailing experience on the York River, Yorktown Sailing Charters offers a highly reviewed, multi-decade operation aboard classic tall ships departing from Riverwalk Landing Pier.
