DOWNTOWN PORTLAND, a peninsula swirling counterclockwise into Casco Bay, lies in thick cultural layers. Starting at New England's third-largest fishing port, Portland Harbor, men and women in foul-weather bibs unload lobster traps and tubs of Atlantic cod. Next is the cobblestoned Old Port, with its boutiques, "commitment ring" jewelers, and Irish pubs. A few blocks away sit the studio and arts districts, with tattooed baristas at gritty cafés, agitprop-chic galleries, and, by sundown, live punk behind closed doors. A quarter of Maine's population lives in and around Portland, but you'd hardly know it come rush hour. Young professionals wear L.L.Bean fleeces and duck boots for all manner of business, even dates, thanks to the company's headquarters being 20 minutes up the road. With relatively mild winters, it's possible to commute by bike almost year-round, and with thick neoprene you can surf in winter. Twenty-six-square-mile Portland has more than 2,000 public-arts events, including free concerts with the likes of Carbon Leaf and the Rebirth Brass Band, and, rumor has it, more ultimate-Frisbee leagues per capita than anywhere else. Maine's highly educated twenty- and thirty-somethings are thick on the ground, keeping their kayaks and snowshoes handy and talking about how they've got it made.

The Perfect 48 Hours
From subscriber Heather Ladd, 30, a 12-year resident who runs her own property-management business:
Load your bike (rent from Gorham Bike and Ski, gorhambike.com) on the ferry for the 45-minute ride to Long Island (pop. 200). Cycle the five-mile perimeter road, stopping for a swim at South Beach and lunch at the Boat House (207-766-5709). The 7:40 gets you back for live bluegrass and the Friday-night $5.95 all-you-can-eat fish fry at the Porthole (portholemaine.com). Eighties dance night at Bubba's Sulky Lounge (bubbassulkylounge.com) is free if you dress the part. The next morning, run the three-mile Back Cove Trail before brunch at Uffa! (uffarestaurant.com). Then launch a kayak (rent from Maine Kayak, mainekayak.com) at East End Beach, watching for pilot whales. After yellow curry at Bangkok Thai (bangkok-thai.com), stroll the waterside Eastern Promenade.

SUPERSIZE ME
Charleston, SC
pop. 106,712
For first-rate Atlantic Coast watersports like surfing, sailing, and sea kayaking, you can't beat metro Charleston's 90 miles of coastline. Culture is both old and new in this 337-year-old port city: Look for homegrown products like aged cigars and black tea, plus a burgeoning design scene and the new Art Institute of Charleston. Throw in a subtropical climate and a refreshingly sane cost of living and you've got a full-fledged urban, and ocean, playground.

READERS' CHOICE
Rockland, ME
"The launching point for gorgeous granite islands." Mish Morgenstern