Chesapeake Bay Yacht Charter

The Chesapeake Bay stretches 200 miles from the Susquehanna River in Maryland to the Atlantic at Hampton Roads, Virginia—and the protected waters in between are some of the best cruising grounds in North America. With hundreds of rivers, creeks, and coves to explore, a charterer could spend weeks without repeating an anchorage.

The historic towns along the Bay are highlights in themselves: Annapolis is the sailing capital of the US East Coast, with a maritime history going back to colonial times. Oxford, St. Michaels, and Chestertown on the Eastern Shore retain their 18th-century character. Norfolk and the Virginia shore offer their own distinct charm.

The Chesapeake is famous for blue crabs—eating them steamed with Old Bay seasoning at a waterfront restaurant is a quintessential Bay experience. The sailing is generally gentle, making it excellent for families and beginners while still offering enough variety to keep experienced sailors engaged.