Cruising Destinations Along The Chesapeake Bay Loop

Tags: Chesapeake Bay Cruising Destinations | cruising destinations | DiMillo's

The Chesapeake Bay Loop offers a perfect blend of natural beauty, history, and great food! Pick a town and travel around The Bay, choosing some great stops on the journey. Here are a few suggestions.


In St. Michaels, Maryland, visit the Chesapeake Bay Maritime Museum to explore maritime history, surrounded by the scenic views of the Miles River.  The 18-acre waterfront museum provides an immersive experience into the rich nautical heritage of The Chesapeake Bay and is a must-see for history buffs and maritime enthusiasts alike.


An adventure along the Chesapeake Bay Loop isn’t complete without a stop in Annapolis, Maryland. Annapolis is Maryland’s Capital and also known as “America’s Sailing Capital”, the town is steeped in maritime history and culture. Historic cobblestone streets lead to trendy boutiques, art galleries, and charming cafés. You’ll also find The United States Naval Academy in Annapolis!


Charming Cape Charles, Virginia boasts beautiful beaches as well as a quaint downtown area. The Cape Charles Museum provides a glimpse into the town’s rich history. Make a reservation at Hook @ Harvey for a wonderful dining experience before you leave!


Cruising the Chesapeake Bay Loop is a journey filled with picturesque landscapes, historical landmarks, and delicious food, making it a perfect adventure!




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