For those who love history, yearn for romance, or have dreamed of experiencing a true sailing adventure, “Your ship has just come in!”

Set Sail for a bygone era aboard the Yorktown Schooners, Alliance and Serenity. You will relive sailing’s golden age as you cruise down the shores of the York River on a traditional schooner past the battlefield where our country won its independence. Their knowledgeable crew will harmonize past with present as you view the Victory Monument, sight dolphins or osprey, sail by working watermen, or perhaps cruise past a naval warship or submarine.

The Ships

The 105-foot schooner Alliance, built in 1995, gets her name from the French and American Alliance that was instrumental in winning the War of Independence in 1781. Alliance can carry 49 passengers on day sails and 12 on overnight sails. Alliance sails in Yorktown for the summer and explores the Caribbean during winter.

Alliance at sunset

Alliance at sunset

The 65-foot schooner Serenity, built in 1986, can carry up to 24 passengers on day sails and is perfect for a smaller group. Both ships offer an amazing experience.

Serenity at sunset

Serenity at sunset

Who Sails?

Groups of all ages enjoy sailing aboard the Yorktown Schooners. From youth groups to seniors and family reunions to corporate functions, cruises can be customized to fit the interest of your group.

Group sail

Group sail

Alliance is handicap accessible with assistance (must be able to go down two steps to get on board, walkers and small wheelchairs accepted). The restroom is down a steep ladder and is not handicap accessible.

When Can We Sail?

There are three cruises daily from April to November. The first cruise takes place 11 a.m. to 1 p.m.; the second is from 2 to 4 p.m.; and the sunset cruise departure time varies with time of sunset.

Types of Cruises

Historic Yorktown 2-hour Cruises  

Lend a hand at setting sail or just relax and enjoy the sights as your group cruises down the York River under a cloud of canvas. You may see dolphins, osprey or working watermen harvesting their catch from the river. The crew will point out the sights as you sail and talk about the Yorktown history. Beverages and snacks are available in the ships’ galley.

Alliance sailing by Riverwalk

Alliance sailing by Riverwalk

Captain Mayhem’s School of Piracy

Serenity pirates

Serenity pirates

Designed for children, Captain Mayhem’s School of Piracy gets kids involved in learning some of the skills necessary to be a successful pirate! The kids will raise the sails, steer the ship, tie a knot and get pirate-themed temporary tattoo. The crew will fire the canon and even be in pirate costumes. These trips are 1.5 hours in duration. Stay tuned for Yorktown’s new adult pirate cruises during select sunset sails!

Private Charters

Yorktown Sailing Charters can customize your charter to fit your group’s needs, including catering and beverage services and personalized themes (such as wine-tasting, history, bay ecology, etc.).


Yorktown Sailing Charters is located at 425 Water St. in Riverwalk Landing Pier, Yorktown Virginia.

The schooners sail in the protected waters of the York River, a tributary of the Chesapeake Bay.

There is convenient motorcoach drop-off on Water Street and public restrooms at the head of dock near the motorcoach disembarking area. Motorcoach parking is located at the County Administration building two blocks up on Ballard Street.

There are many shops and restaurants within walking distance at Riverwalk Landing. You may also be interested in visiting Yorktown Victory Center, Yorktown Visitors Center, the battlefield, Watermen’s Museum, antique shops, art galleries, the public beach and picnic area.

Alliance sailing

Alliance sailing past Yorktown

How Much?

Public Sailing Rates:

2 hour morning and afternoon sails:  $35 adults, $20 children 12 and under

2 hour sunset sail: $35 per person (no child discount)

There is a 10% discount for groups of 20 or more on public cruises. There is free admission for the tour operator, escort or driver.

Private Charter Rates: 

Schooner Alliance (maximum of 49 passengers, including tour operator)

Travel Industry discount on private charter rates:

2 hour morning or afternoon sails: $1300

2 hour sunset sail: $1400

Saturday charters $100 more

Schooner Serenity (maximum of 24 passengers, including tour operator)

2 hour morning or afternoon sail: $750

2 hour sunset sail: $800

Saturday charters $50 more

Steering lesson

Steering lesson

5 Tips for Planning a Cruise with Yorktown Sailing Charters

  1. Before or after your cruise, relax on the river’s sandy beach; stroll along the scenic river walk; stop in art galleries and antique shops; or visit museums with hands-on exhibits. Seeing the area on land will further enhance your nautical perspective!
  2. If you can, book a cruise during one of Yorktown’s events and festivals.
  3. Reserve a box lunch during a cruise; snacks and drinks (including beer and wine) are available onboard, but if you choose to help man the sails and steer the ship, you will surely work up an appetite.
  4. Plan ahead! Cruises fill up quickly.
  5. If you’re considering a Caribbean cruise, call well ahead of time to discuss all your options, amenities and details; Yorktown Sailing Charters has so much to offer!

By Lauren Reiniger