The Bay & Beyond

What’s a boater to do? Now that you and your family are having to spend more time at home, why not take this opportunity to take “home” with you. Explore some new places on the Chesapeake Bay and even beyond—hey, the winter is warmer down south, you know. With that in mind, we’ve picked a few of our favorite places for you to discover, or rediscover. So come on, let’s go!

We’ll start at the top, with this charming city at the gateway to the Chesapeake & Delaware Canal. You’ll want to come here for the old-world charm (it’s on the National Register of Historic Places) of its homes and shops. Dock the boat at one of its marinas or take an excursion along the canal. Antiques shops, delightful restaurants and ice cream too. What’s not to love? For a bonus, try out nearby Havre de Grace.

If you have not yet made the trip to the Eastern Shore to explore Rock Hall, now’s the time! There’s a reason its natural harbor and back door, Swan Creek, are chock-a-block with great marinas. This tiny town is both a picture-perfect example of a classic waterman’s town and the perfect opportunity to indulge in local seafood while enjoying some of the best sunsets ever. Want more? Head up the gorgeous Chester River to Chestertown.

Come to Herring Bay for the fishing, for the restaurants, for the famous resort marina, Herrington Harbour. Or drive down and launch your boat for day trips while staying in its hotel or resort facilities. Bring your paddle craft to explore the nearby creeks. Ever been to a great Bay dock bar? Here’s your chance. Bonus side trip: If your draft will allow, try nearby Chesapeake Beach.

No discussion of Bay cruising would be complete without a nod to the star of Chesapeake boating destinations, St. Michaels. This Eastern Shore village has it all: a first-class maritime museum, excellent marinas, its own brewery and distillery, an elegant full-service resort, and enough restaurants to keep you full to bursting for weeks. Bonus: Explore the marvelous Wye River just next door.

Welcome to the twin cities of the Chesapeake! Each has its own special personality and charm. You won’t want to miss either. And you don’t have to, because they are connected by water taxis that run regularly. Portsmouth has its magical Old Town, with historic homes and churches and eclectic restaurants. Across the Elizabeth River, Norfolk has Granby Avenue, lined with shops and restaurants, a very big battleship to call its own, and Nauticus, a maritime museum like no other. Oh, there’s plenty more!

Wait a minute, we hear you say, that’s two destinations. Yes, you are right, of course, but we say why not take advantage of both while you are at it? In Yorktown, you’ll find a month’s worth of history lessons for the kids, while you all enjoy a lovely beach, restaurants and shops. In Hampton, the history lesson will continue in the pleasantest way in Old Town and at the Virginia Air & Space Museum. Ride a historic carousel and dine on 21st century cuisine and local seafood.  Bluewater Yachting Center, a luxury marina within a short dinghy ride of downtown Hampton, is a great base to explore from.

The first two of our Beyond the Bay destinations can be done separately or as one easy loop. Head south out of the Bay using either the Albemarle & Chesapeake or the Dismal Swamp routes and return using the other. The distance is nearly the same but the experience is very different. While planning your trip, check out the Albemarle Loop.

Here’s a destination you’ll love! It has the mystery of the Lost Colony of Roanoke, great fishing, plus great marinas and shopping. Turn east on Albemarle Sound and head for the eastern side of Roanoke Island. Inside Shallowbag Bay, you’ll find marinas, free docks and easy access to the town of Manteo. Your feet will get you to everything else. Don’t want to come by boat? Then come and try out one of Manteo’s B&Bs or hotels. Bonus side trip: The Outer Banks’ town of Ocracoke is an easy trawler day away.

If you turn west on Albemarle Sound after entering from the Chesapeake, you will come to the positively elegant town of Edenton. Its marina lies inside a breakwater with a remarkably beautiful view of the sound and the city. The main street features busy shops and restaurants, as well as walled gardens, dazzling in their blooms, and 17th and 18th century mansions, churches and commercial buildings. Here, beauty is all around you.

If you’re heading down the Intracoastal Waterway, you’ll find Belhaven just after Albemarle Sound and the long and lonely Alligator-Pungo Canal. This makes Belhaven a favorite cruisers’ stop, for its marinas, access to groceries and charming Victorian homes. It also boasts a great restaurant, an ice cream shop and a downhome breakfast café. Add fuel and a pump-out and you’re ready to go!

Here is another of our all-time favorite destinations. Georgetown is a perfect cruising stop. Located along the ICW at the south end of the wonderful Waccamaw River, Georgetown for centuries has offered a protected port for seafarers, with access to the ocean by way of a good inlet, or the continuation of the ICW route toward Charleston. Restaurants? Yes! Lovely homes on streets shaded by ancient oaks? Yes! Enough said.

How do we extoll the virtues of this most popular of ICW destinations in 50 words? We don’t need to because we know you already have Charleston on your wish list. By boat, try the Charleston City Dock’s quarter-mile-long Megadock. It’s a rite of passage. Then cut loose and revel in the history, restaurants and charm of this old city.

You might think that by this time we must have run out of superlatives. Heck no! We are going to pull out a few more to describe this classic example of Southern charm. Bigger than Georgetown and smaller than Charleston, Beaufort is just about perfect. Stay at one of its three excellent marinas: one in town, one across the bridge on Ladys Island, the third downriver at Port Royal. Paddle, explore, relax and enjoy.