Chesapeake Bay Cruising: Where to Go and Where to Dock

The Chesapeake Bay, the nation’s largest estuary, offers adventures for every kind of boater. Whether you want to pull up at a full-service marina in Annapolis for access to the city or you want to get off the beaten track for some quiet fishing, there is a place for you on the Chesapeake. The Bay is also packed with marinas with fuel, boat slips, and restaurants for when you need a break from the water. If you’re preparing to explore the Chesapeake, here are some adventures you might want to consider.


Annapolis, Maryland’s capital city, is home to history, art, shopping, and fine dining. There is lots of activity around the city dock area, including restaurants and shopping, and you can also dock your boat and paddle closer to the shoreline in a kayak. With your boat in a marina slip, you can head downtown to tour the city on foot or head to the grounds of the Naval Academy. The Chesapeake Harbour Marina offers affordable boat slips in a resort-style marina and is the perfect launching place for your exploration of Annapolis.

Severn River

The Severn River is one of the tributaries of the Chesapeake Bay and flows into the Bay less than three miles from Annapolis. It’s a popular destination on the Bay for its abundant fish—almost everyone is sure to get something on his or her line here. The most common fish are smallmouth bass, catfish, perch, rainbow trout, and bream, but others are abundant as well. Fishing licenses are available from the Maryland Department of Natural Resources. The Chesapeake Harbour Marina is nearby and a great place to dock for the evening.


Deale is a small fishing town about 20 miles south of Annapolis. It’s a popular destination with locals and tourists alike looking for a laid-back town with plenty of fish biting. Waterside restaurants and bars dot the Deale coastline and are popular for casual meals and relaxation. There are small marinas in Deale to dock your boat, and it is within easy reach of the Chesapeake Harbour Marina if you want a full-service marina experience after a daytrip down the coast to Deale.


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