Some of the prettiest ports in the country are located in the southern stretches of the Chesapeake Bay, in eastern Virginia, where waterfront towns have both long and rich histories and the kind of laid-back lifestyle that appeals to those who crave a quiet escape. Cruisers come here for those peaceful mornings on the hook, with a light breeze coming slow and easy out of the west, blowing over a creek that's glassy and calm. And there are ports in this region of the bay to suit different sensibilities. While the eastern side of this section of the Chesapeake is more clapboard houses and salt marshes, the western shore is colonial brick and rolling hills. Here are four great places to visit.
Located along the banks of Carter Creek on the western shore, a tributary of the Rappahannock River, it was once a popular spot for oyster pirates and hosted some of the south's most distinguished families, from state governors to Civil War heroes. Irvington once thrived as a regular stop for steamboats carrying goods and travelers across southern Chesapeake Bay, which is why The Steamboat Era Museum is a popular stop for visitors; displays include models of ships and steamboats. For more history, head to Christ Church (finished in 1735), where you can learn about the area's Colonial history and tour one of the nation's finest examples of Georgian architecture. For provisioning, hit the farmers' market at Irvington Commons for fresh seafood, meat and vegetables. For an elegant wine to pour with dinner, visit one of the vineyards in the area such as The Dog and Oyster Vineyard, owned by Hope and Glory Inn. While you're calling on these places, enjoy the southern hospitality that still runs in the heart of this community.
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Deltaville has been dubbed Boating Capital of the Chesapeake for good reason. This beautiful, rural peninsula hosts 24 marinas and 10 boatyards. Its location makes it a popular home port as well as a convenient cruising destination. If you need anything for your boat, you can find it here: service, provisions, marine supplies, all served up with welcoming smiles. Deltaville residents take pride in their community and love to share a lifestyle of fishing tournaments, sailing races, local festivals and firehouse dinners. There are consignment and antique shops to browse on a lazy day in port and if you are in the mood for some touring, head for Deltaville Maritime Museum in Holly Point Nature Park. The museum chronicles the history of Chesapeake Bay watermen and its 36 acre park features outdoor sculpture gardens and a venue for waterfront plays and concerts. If you have time, see the tip end of Deltaville, called Stingray Point. Local lore says Captain John Smith was stung by a stingray here and was given the antidote for the bite by local Native Americans.
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Some cruisers who have visited this former railroad town at the tip of Virginia's eastern shore say it's one of the Mid-Atlantic's best-kept secrets, though a hot second-home real estate market in recent years has put it on the radar of more out-of-towners, so it's no longer a place where residents know everyone's name. Life is flip-flop easy, with bikes and golf carts sufficing for transportation and menus heavy with local seafood (this area is thriving with Little Neck Clam aquaculture farms). Start your day with a hearty breakfast from the Cape Charles Coffee House, housed in a beautifully restored 1910 haberdashery on Mason Street. For lunch check out Kelly's Gingernut Pub, which serves lunch in a 106-year old former bank building. Save room for dinner on bistro nights (Tuesday through Thursday) at Hook U Up Gourmet where you can sample local seafood or indulge with a steak dinner that will easily fill you up. And for your sweet craving after dinner head down the street to the Brown Dog Ice Cream.
Save time for shopping at the many boutiques and galleries on Mason Street and then head to the beach at the end of the street this long, quiet beach is a great place for kids to collect periwinkles on sandbars. Cape Charles can seem charmingly rural, with oyster roasts at the historical society a popular community event. But there's an upscale edge, too. The Hotel Cape Charles is a very cool, new, upscale boutique hotel in the heart of town. Golfers can play The Jack Nicklaus Signature Golf Course at Bay Creek Resort. Enjoy the total Cape Charles experience and attend Fall Festival (October 11) with live music, artisans, crafts and food.
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Onancock is a hamlet on Virginia's eastern shore, poised on a peninsula and surrounded on three sides by water. Here, the Onancock Creek courses for about five miles to empty into the Chesapeake Bay. Easy schooner access to the bay made Onancock a shipping hub as early as the late 1600s, and it's proximity to the peninsula's rail line kept that going into the 20th century. Today, the artists, entrepreneurs, retirees and tourists drawn to this small and walkable town still love it for the water, the open land that surrounds it, the leafy quiet and the wharf with its compact commercial district, which sends the friendly message that Onancock is also a working town.
There are plenty of entertainment options in town such as the North Street Playhouse, the Roseland classic old-time movie theater (built in 1950) and a variety of galleries and boutique shops including Dawn, which sells everything from home furnishings to women's clothing, and Willie Crockett's art gallery and studio on Market Street. This fall, one of the most significant collections of antique maps and original Audubons ever assembled in Virginia is traveling to Onancock for a special exhibit at the Eastern Shore of Virginia Historical Society Ker Place Museum. You can visit Tangier Island by ferry from the marina, only a 4-mile trip that runs daily (except Monday) from May through September. There are also plenty of great dining options in town from Mallards at the Wharf (with outside seating and amazing homemade crab cakes) to the Corner Bakery to satisfy your sweet craving (their cream puffs are to die for).
If you want to get out on the water, you can charter a fishing boat, rent a kayak from Southeast Expeditions, next to the marina or drop a fishing line from the wharf with the locals. There is truly something for everyone in this small, friendly town.
Where to Dock