Portland

Sitting on a peninsula that juts into the icy waters of Casco Bay, Portland wears many hats: New England’s largest port, a most vibrant small city, and a lively historic background with its start as a fishing village in 1633. It boasts of an impressively widespread food scene, a lively waterfront, fantastic art galleries and museums, and attractively restored redbrick buildings, filled with cafes, pubs and shops. You’ll want to explore for weeks.