Maine's largest city, Portland sits on a peninsula extending into scenic Casco Bay. This historic city has plenty of charm -- especially the renovated Old Port, with its brick sidewalks and cobblestone streets. In addition, travelers who stop here are rewarded with ferries to islands, boutique shops, some top-notch historic homes, graceful neighborhoods -- and the food. Portland is a culinary mecca of Maine, blessed with an uncommonly high number of excellent restaurants for a city its size.

Any visit to Portland should start with a stroll around the historic Old Port. Bounded by Commercial, Congress, Union, and Pearl streets, this area near the waterfront contains the city's best commercial architecture, a mess of boutiques, fine restaurants, and one of the thickest concentrations of bars on the eastern seaboard. Its narrow streets and intricate brick facades reflect the mid-Victorian era; most of the area was rebuilt following a devastating fire in 1866. Leafy, quaint Exchange Street is the heart of the Old Port, with other attractive streets running off of and around it.