No matter where you are from, it’s difficult to visit the city of Portland and its surrounding area without being tempted to move there. For starters, the city has all the sophistication of an urban center twice its size, with its performing arts centers and galleries, top-notch museums, and indisputably creative restaurants. But it also boasts all the benefits of a small town—residents are genuinely friendly, cafés are full of locals, streets are kept clean, and there is almost completely unfettered access to the area’s many parks, beaches, and countryside.

Maine’s largest city, Portland proper has a population of about 70,000, while its greater area is home to about a quarter of a million. With an impressive stable of cultural resources (from the renowned Impressionist collection at the Portland Art Museum down to small historic sites such as the Wadsworth-Longfellow House) and a citizenry that stays active in the community year-round, the city has long since transcended the summer-only appeal of many seaside cities.

Outside city borders, things quiet down dramatically in suburbs like Westbrook, Gorham, and Cumberland. Those pretty bedroom communities still have their own seasonal attractions, however: namely picturesque beaches, lighthouses, woodland parks, rivers seemingly built for white-water rafting, hiking and biking trails, and nature preserves.

It isn’t far, either, to the rest of the South Coast—a collection of historic communities ranging from once-prosperous and now-touristy to once-prosperous and still-prosperous. Each has its own character and abundance of coastal must-sees. In the historic Kennebunks, spruced-up sea captains’ houses and Victorian mansions are as plentiful as tony inns and rocky beaches. Kittery and Freeport are a bargain-hunter’s bliss, brimming with enough international designer outlets to fill a thousand wardrobes and years of holidays to come. (The more, shall we say, aggressive shoppers have been known to leave stocked up on Christmas gifts for the next decade.)

The seaside community of Ogunquit is a magnet for urbanites looking to relax among, well, other relaxing urbanites—without sacrificing the sophisticated restaurants, high-quality boutiques, or maddening dearth of parking they’ve become accustomed to in the city. On the other end of the aesthetics spectrum sits Old Orchard Beach, home to a kitschy-as-can-be old-school amusement park, complete with rickety roller coasters, arcades, cotton candy stands, and all the vibrant people-watching you can handle.

The Best of Portland and the South Coast

• Old York Historical Society
• Marginal Way
• Perkins Cove
• Portland Head Light
• Portland Museum of Art
• L. L. Bean Factory Store