This post will focus on the northern part of the Chesapeake Bay, and the area surrounding Annapolis: Maryland's capital.
Tilghmam Island, to the southeast of Annapolis sits on the eastern shore and is home to gorgeous natural beauty and amazing seafood.
If you happen to be cruising through the Chesapeake in late June, you’d be silly not to stop at Tilghman for their annual Seafood Fest, which is quite possibly the best crab festival around. Tilghman’s history includes a proud oystering tradition, which used to be done on Skipjacks: sloop-rigged sailboats with long bowsprits that would be used for dredging the bottom of the bay for oysters. You can see some of the remaining and most historical Skipjacks on Tilghman Island.
Be aware about your approach to Tilghman Island though, as there is a drawbridge that separates the island from the mainland, and going under the drawn bridge is tricky: it’s narrow and shallow so watch out for running aground.
Where to dock: Tilghman Island Marina
Don’t miss: The fishing around Tilghman Island
Rock Hall (love the name of this town) is also on the Eastern shore, but a bit further north of Annapolis and the rest of the locations on this list. It’s known as a cozy town that takes it seafood very seriously, as it’s proximity to the water and boating heritage. If you’re visiting Rock Hall, you should consider taking a stroll around town (known as the Rock Hall “loop”) or perhaps rent a bike and cruise down to the Eastern Neck wildlife refuge to the south, where bird watching (over 243 species of birds call it home) is serious business.
Of course, the can’t miss spot in Rock Hall is Waterman’s Crab House, which is famous for it’s awesome eats and fun live music and festivals.
Where to dock: Haven Harbour Marina
Don’t miss: Waterman’s Crab House
Galesville is located on the western shore, just to the south of Annapolis. The approach to Galesville from the north and Annapolis takes you right past Thomas Point Lighthouse, which is an original screw-pile lighthouse, and the only one of its kind that still resides at its original site in the Chesapeake Bay. The lighthouse is an iconic symbol of Maryland and the Chesapeake Bay, so don’t miss it of you’re cruising! Galesville itself is a sleepy town, but has some great scenery on the West River and is an excellent harbor to stop it, especially if you’re cruising on an overnight out of Annapolis.
Where to dock: Hartge Yacht Harbor
Don’t miss: Thomas Point Shoal Lighthouse
Kent Island is located just to the north of Tilghman Island and to the south of Rock Hall on the eastern shore of the Chesapeake. It’s the largest island in the Chesapeake Bay and sits virtually in the middle of the Bay, making it an ideal destination to cruise to. The island is connected to the mainland through the Kent Narrows, which you can pass through to access the southern portions of the island.
Highlights of the Kent Island area include some awesome crab houses, both on the island and just off of it in nearby Grasonville, MD. We recommend staying at a marina in Kent Narrows, which will give you access to the whole area, as it’s very central. Day trip sail or motor up Cox creek is a gorgeous way to spend a day, you won’t regret it!
Where to dock: Piney Narrows Yacht Haven
Don’t miss: Harris Crab House near Kent Narrows (especially in crab season!)
The city that’s widely considered the center of the Chesapeake Bay for all things boating (heck the Naval Academy calls Annapolis its home) is also a mecca for history buffs and foodies alike. The city is about 30 miles east of Washington DC, right on the Severn River, about halfway up the Bay on the western shore. Annapolis is knows for it’s sailing heritage with its many marinas and Yacht Clubs that often host sailing events and regattas.
Annapolis is a great spot to use as a jumping off point for cruising the whole Chesapeake, but you definitely also want to spend a few days there exploring also. There are a host of restaurants, tours and other stuff to do in the city, so have some fun!
Where to dock: Port Annapolis Marina
Don’t miss: Get a tour of the US Naval Academy
Image credit: tilghmanisland.com