Cruising the Chesapeake Bay

Tags: Chesapeake Bay | Chesapeake Bay Cruising Destinations | Cruising the Bay | DiMillo's Maryland | DiMillo's on the Chesapeake | Maryland | MD

The Chesapeake Bay is the largest estuary in the United States, and third largest in the world. Calm waters and sheltered tributaries provide pleasant boating on The Chesapeake. Spanning an area of over 4,400 miles, The Bay offers plenty of fantastic destinations! Featured here are a few favorites.


St. Michaels, MD: This colonial seaport is a must visit when cruising on the bay! Countless restaurants and small shops fill the streets. Eastern Shore Brewing and St. Michaels Winery are local stops to whet your whistle while you’re in town. Step back in time at the Chesapeake Bay Maritime Museum, an interactive museum highlighting the history and culture of the Bay.


Oxford, MD: One of Maryland’s oldest towns, Oxford was founded in 1694. Visitors enjoy wandering the quaint streets and finding hidden treasures in several of the local shops, like Oxford Vintage and Trade. The Oxford Bellevue Ferry is located here and is the oldest in the nation! Stop by Scottish Highlands Creamery for some award-winning ice cream and take in the views of the Tred Avon River from Oxford Park. Oxford Bonus – Our newest DiMillo’s location – DiMillo’s on the Chesapeake East – is located downtown!


Smith Island, MD: The only island inhabited island in Maryland that is not attached to the mainland by bridge or causeway, Smith Island is named for Henry Smith of Jamestown, when he was granted 1,000 acres there in 1679. Though small and walkable, golf carts are the preferred transportation around the island. You can’t leave without a slice of Smith Island Cake – the official dessert of the State of Maryland – a 3-inch-tall dessert packed with 10 layers of cake and icing!


Tangier, VA:  A 1 mile long by 3-mile-wide island sitting in the middle of the Chesapeake Bay, Tangier Island is accessible only by boat or plane. Such a small island would indicate it’s possible to explore it over a couple of hours but the striking heritage and unexploited natural beauty lead to the possibility of many hours on a golf cart or bicycle to soak in all the island offers. Stories of the Island that date back hundreds of years are shared at the Tangier History Museum. Tangier Island is known for its soft-shell crab sandwiches, among other seafood dishes, and a visit there isn’t complete without sampling the delicacies.


Cape Charles, VA: Boasting one of the largest concentrations of late Victorian buildings on the East Coast, most of the buildings here were built between 1885 and 1920. For the nature lovers dropping anchor at Cape Charles, Kiptopeke State Park is famous for hawk observation during the fall migratory season. Two signature golf courses, designed by Arnold Palmer and Jack Nicklaus, are featured at Bay Creek Resort.


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