A small yet sophisticated charmer on Virginia’s bucolic Northern Neck, Irvington’s remoteness may appeal to those no longer commuting. Spend your work-free days here enjoying life at the tasty crossroads of both the Chesapeake Bay Wine Trail and the Virginia Oyster Trail. A plethora of Bay recreation opportunities are close at hand and when feeling a little indulgent, head off to the world-class Tides Inn resort for dining, golf, or some spa time. Just minutes away, the larger town of Kilmarnock is a hub of commercial activity (i.e., has a Walmart), leaving Irvington’s tiny core a quiet home to eateries, a steamboat museum, and an historic inn.
Niche rating: A for retirees
Eastern Shore alternative—Cape Charles, Va. (pop. 1,000) This 19th-century town’s cute restaurant- and shop-lined main drag ends at a capacious public Bay beach. While it feels remote, it’s less than an hour from Norfolk and Virginia Beach. The Bay Creek Resort includes both Arnold Palmer and Jack Nicklaus signature golf courses. Coastal Living calls it the “Cinderella of the Chesapeake,” ranking it the “Third Happiest Seaside Town.”