Where are you planning on cruising next summer?

November 12, 2019

Check out some of my favorite destinations on the Chesapeake Bay

By Desiree van Welsum on November 12, 2019

Have you just bought a boat at one of the Fall boat shows and are you thinking about different areas to go cruising? Are you up north and about to winterize your boat for the winter, thinking about next season’s trips? Are you a crew member planning next Summer’s cruising program for the boss’ boat? Here are some of my favorite cruising destinations on the Chesapeake Bay.


Whether you want to escape the Florida heat for the summer, or maybe you are just passing through, perhaps as part of doing the American Great Loop, the Chesapeake Bay offers an amazing cruising ground with lots of great boating destinations within easy and short cruising distance. Depending on how much time you have, you could base yourself for example in Annapolis or Baltimore (both offer great access to several airports and railways stations) and undertake short trips from there, or make it a Chesapeake Bay cruise.

We like to use Annapolis, Maryland, as our summer base, and take trips from there. Annapolis is a great town, and is often called “the sailing capital of the United States.” It has a beautiful historic downtown on the water, is home to the United States Naval Academy, and hosts two great boat shows in the fall (the Annapolis Power and Sailboat Shows). Check out my previous blog for some tips for things to do in and around Annapolis. [click here]

Going north from Annapolis, our first destination after passing under the Bay Bridge is Baltimore. The city of Baltimore has put a tremendous effort into redeveloping the water front and what is called the Inner Harbor, with several nice marinas and lots of shops and restaurants within easy walking distance. The innovative @MrTrashWheel is a great help in cleaning up the Inner Harbor. We also enjoyed picking up one of the little step scooters that people zoom around town on and explore some of the nearby areas such as the historic neighborhoods of Fells Point and Little Italy. Both the football stadium and baseball stadium are in town and attending a game with the locals is always fun. The city skyline at sunset and by night are an amazing sight to enjoy from your boat.

Crossing over to the Eastern Shore from Baltimore, the first stop is Rock Hall, with some nice marinas, anchorages and restaurants. Cruising south from Rock Hall, it is worth taking a detour on the beautiful Chester River to visit Chestertown. Chestertown is a pretty town with a great market in the center of town on Saturday mornings. In early Fall Chestertown hosts the impressive annual Downrigging Festival.

Going further south on the Eastern Shore, my next favorite stop is the town of St Michaels, or “The town that fooled the British.”[1] It is a very pretty town with a historic center, beautiful homes, lots of great restaurants, ice cream stores and coffee shops, a brewery and distillery, the Chesapeake Bay Maritime Museum, and several marinas right in the center of town. St Michaels also hosts the annual Concours d’Elegance in September, as well as other festivities throughout the season.

Continuing further south on the Eastern Shore, the next stops are Oxford and Cambridge. Oxford is another very pretty town, home to several boat builders, and the Robert Morris Inn where the author James Michener outlined his famous novel, Chesapeake. In Cambridge, you will also find a nice ‘resort marina’, if you are in the mood for some golf, pools and spa treatments.

Continuing further south on the Eastern Shore, you can use the town of Crisfield as a base to take the ferry to explore Smith Island, with its famous Smith Island Cake (Maryland’s official state dessert since 2008[1]), and Tangier Island, home to the renowned Crab Shanties and the Tangier Island Watermen. Sadly, this island is affected by erosion and is slowly disappearing, sinking into the Bay.[2] Cape Charles, would be the southernmost stop on the Eastern Shore, another town with a pretty historic district, beautiful sunsets, and several marina options. While cruising the Chesapeake Bay, try attending a Chesapeake Cowboys Boat Docking Competition, one of which is also held in Cape Charles.

From there, cross back over to the western side of the Bay. As mentioned in a previous blog, we like to stop in Irvington, Virginia [click here]. Solomons, with its Calvert Marine Museum, and the nearby Calvert Cliffs where it is fun to look for shark teeth on the beach, is a nice stop to make on the way back to Annapolis. On your way back you will pass Thomas Point Shoal Lighthouse, one of many beautiful lighthouses on the Chesapeake Bay.[3]

Going to visit the nation’s capital is worth a separate side trip. From the Chesapeake Bay you will make your way up the Potomac River, passing an active firing range,[1] Marine Corps Base Quantico (made famous by numerous TV shows), the Ghost Fleet of Mallows Bay which is fun to explore by anchoring nearby and carefully kayaking through the submerged and semi-submerged wrecks,[2] Mount Vernon (George Washington’s house overlooking the Potomac),[3] Fort Washington,[4] National Harbor (with a marina, restaurants, and an MGM Casino), Old Town Alexandria (with another marina), and Washington National Airport, before arriving in Washington DC, or DC for short.

Much of the DC water front has been completely redeveloped and offers several nice options for cruisers. We like the Yards Marina on the Anacostia River by the old Navy Yards, situated at the heart of a nice waterfront neighborhood with a great selection of restaurants and all amenities and conveniences nearby, not to mention just a 5 minute walk from the baseball stadium, home to the 2019 World Champions, the Washington Nationals!

The Wharf is another redeveloped waterfront area with several marinas on the Washington Channel, restaurants and a great new concert venue The Anthem, and the old fish market. This area is a little more lively and touristy than the Yards neighborhood, so we prefer to just dinghy over to it from the Yards.

A third fun waterfront area in DC is in Georgetown, but getting there via the water is subject to a height restriction on the railroad bridge (18’ clearance). We like to take the dinghy over to Georgetown, a charming historic neighborhood (DC’s oldest) with cobblestone streets, great shops, a movie theater, and several nice restaurants on the waterfront. Going to Georgetown takes you past several of the famous DC Monument, including the Jefferson Memorial (also referred to as The Muffin), and the Lincoln Memorial, as well as the Kennedy Center, and the famous Watergate Complex and Hotel. You can rent paddles boards and kayaks from the Key Bridge Boathouse to explore the waterfront, and continue further north on the Potomac, past three rocky islands in the middle of the river known as the “Three Sisters”, and all the way up towards Great Falls.

Finally, don’t leave the Chesapeake Bay without trying one of its famous crab delicacies, like Maryland Crab Soup, or just spend some time with friends picking freshly steamed crabs.[1] Indeed, at most of the waterfront restaurants on the Chesapeake tables will be covered in paper and the staff will bring out little wooden hammers, trays full of crabs covered in the local spice “Old Bay,” and little buckets for the shells and claws. Be sure to stock up on some Old Bay too, it adds great flavor to all of your dishes, especially my personal favorite, Old Bay French Fries!

In sum, there is no shortage of great destinations on the Chesapeake Bay, so be sure to pay it a visit next time you get underway. After all, the best way is under way!

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