A trip to Portland, Maine, is much more than flannels and Subarus—although you'll come across plenty of those, too. Maine's largest city, surrounded by water, is as picturesque as they come, with quaint cobblestone passageways and Victorian dream homes. Breathe in the fresh New England air while exploring the Old Port, sift through treasures at the vintage shops, and eat your way through the city's award-winning restaurant scene. More oysters? Don't mind if I do.