Annapolis, MD
The United States Naval Academy and St. John's College anchor this small capital city with a stunning waterfront, rich boating culture, and proudly preppy residents. Experience the town as it's meant to be seen–from the Chesapeake–by booking a sailboat tour or taking a water taxi to Restaurant Row, where visitors head to Carrol's Creek Waterfront Restaurant for Maryland's famous crab cakes and harbor views.
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