The Chesapeake Bay Wine Region offers a relaxed, coastal twist on Virginia wine country, where creekside docks, historic villages, and vineyard rows all seem to end at the water’s edge. Centered on the Northern Neck and Middle Peninsula, this waterfront region pairs scenic drives with gentle breezes off the bay and a slower pace that invites you to linger over every glass.
Anchored by the Chesapeake Bay Wine Trail, the area features a collection of boutique wineries and a cidery that wind past rivers, inlets, and sandy shores. Along the trail you’ll find estate-grown, hand-crafted wines at longtime producers like Ingleside Vineyards—one of Virginia’s oldest wineries—as well as welcoming porches and courtyards at spots such as Good Luck Cellars, The Dog and Oyster, Jacey Vineyards, Monroe Bay Winery, Rivah Vineyards at the Grove, Ditchley Cider Works & Farm, and others.
Celebrated for its wine-and-oyster events, historic manor houses, and inviting B&Bs overlooking the vines, the Chesapeake Bay Wine Region has earned recognition as one of Virginia’s most charming wine trails. Whether you’re planning a laid-back afternoon of tastings, a seafood-focused weekend getaway, or a longer road trip that links coastal charm with classic Virginia varietals, this area is an easy-going, scenic escape that rewards slow travel and a second glass.