Mooring Up on the Virginian Towns of Chesapeake Bay

Chesapeake Bay spans over 320 miles, beginning at the Susquehanna River and flowing out into the Atlantic Ocean. With a bay of such magnitude a sailor can’t expect to experience the versatility that it has to offer in one go-around. Split between Maryland and Virginia this bay makes travelling preparations mandatory. Here are some of the most appealing sites that Virginia has to offer.

Cape Charles

As one of the earliest settlements in North America, Cape Charles is steeped in colonial history. Though it was once a populous town it is now home to just over 1,000 residents. Located just 10 miles north of the Atlantic, Cape Charles’ ample supply of golf courses, B&Bs, and coastal themed restaurants make it the perfect place to start or end your Chesapeake Bay sailing jaunt. If you’re a beach-bum it’s important to note that this homey town has the only public beach on the Eastern Shore of the bay.


Hampton not only boasts expansive beaches that span for miles but the NASA Langley Research Center as well as the Virginia Air and Space Center. After you’ve docked up be sure to make your way to the Virignia Air and Space Center to find out about the discoveries of the universe. After you’ve explored the vastness of the cosmos you can partake in a sporting event of show at the Hampton Coliseum. For an excursion that’s sure to get the kids excited you can head over to the Bluebird Gap Farm. The 60-acre farm is home to a number of animals that visitors are free to feed and pet. It also features a designated picnic area as well as a playground.


Irvington is a boat friendly town that offers a number of marinas where bareboat sailors can reserve a dock spot for a fee. After docking visitors can either walk or take a short bike or taxi ride into town. Irvington provides that homey setting that most sailors will want after a day of sailing and in 2000 this ethos was validated by being added to the list of the National Register of Historic Places. The town commons is a major destination that offers a ball field, playground, tennis courts, gazebo, summer concerts, and a farmer’s market during the summer.

With a host of cities and towns receptive to seafarers, Virginia offers much more than can be experienced in one Chesapeake Bay sailing vacation.