Seagulls scream, the smell of beer and fish fry flows through the streets like the fog off Casco Bay, and everywhere the salt wind licks your skin. Maine's largest city has capitalized on the gifts of its port history – the redbrick warehouse buildings, the narrow cobblestone streets – to become one of the hippest, most vibrant small cities in the Americas. You'll find excellent museums and galleries, abundant green space, and both a food culture and a brewing scene worthy of a town many times its size.
Set on a peninsula, Portland's always been a city of the sea. Today, the Old Port district is the town's historic heart, with handsomely restored brick buildings filled with cafes, shops and bars. There are more hipsters than fishmongers living here these days, but there's also genuine ethnic diversity – Portland boasts a large African population – generally lacking in the rest of Maine.