Concierge.com's insider take:
Maine's biggest city leavens its Norman Rockwell charm with a cosmopolitan edge. Stroll through downtown (known as the Old Port District) and you'll find cobblestone streets and turn-of-the-century brick buildings that now house clothing boutiques, art galleries, coffee shops, and stores selling the requisite Maine kitsch: blueberry jam and lobster hats. Restaurants such as DiMillo's Floating Restaurant line the fishing wharves, which are still active with lobster boats and ferries. By night, a dynamic bar scene, fueled by live music and locally crafted beers, takes over Fore Street in the Old Port, while clans of young artists congregate in the lounges of the Arts District. As for the art itself, the Portland Museum of Art hosts rotating exhibits and has an impressive permanent collection that emphasizes Maine paintings and photography (7 Congress Square; 207-775-6148; www.portlandmuseum.org). To appreciate the breadth of Portland's underground arts scene, check out the First Friday Art Walk, held the first Friday of every month, when 50 or so independent galleries open their doors for wine-and-cheese receptions and the chance to gab with the artists (www.firstfridayartwalk.com). If you want to blend in with the local hipsters, swing by Rogues Gallery's flagship store to pick up one of their nautical-meets-naughty handprinted shirts and hoodies (41 Wharf St.; 207-553-1999; www.roguesgallery.com).