Bumped up against breezy Casco Bay, Portland is one of the last working waterfronts in the country. Founded in 1632, it soon prospered as the primary point of trade between Canada and Europe. Today it still serves as New England’s second-largest fishing and oil port and its largest port for tonnage.
All of which could have made Portland into an unattractive, polluted, industrial-looking town. But nothing could be further from the truth. Anchored by its Old Port district, the city is filled with art galleries, pubs, museums, chic bistros, and independent boutiques. Its cobblestone streets and squares are serenaded by the cries of seagulls and foghorns, and its high-rise buildings (Portland is a regional center for banking and import/export) are met with the historic charm of revitalized brick warehouses now used for retail, offices, and artsy movie houses.
The proliferation of those warehouses is actually the result of the city’s greatest tragedy; in 1866 a fire swept through almost all of the neighborhoods, destroying most of the previous architecture. The brick warehouses were built in its place, giving a pleasing uniform look to the waterfront area of the city.
Its outlying towns—South Portland, Scarborough, Cape Elizabeth, Cumberland, Falmouth, and the Casco Bay Islands—are primarily bedroom communities. But in them you’ll find excellent historic inns, world- famous lighthouses, and pristine beaches.
Portland is serviced by Portland International Jetport (1001 Westbrook St., 207/774-7301, www.portlandjetport.org ), from which United, Delta, Continental, Northwest, and USAir all fly. There you’ll find national car rental agencies Alamo, Avis, Budget, Hertz, and National. By train, the Amtrak Downeaster (800/872-7245, www.thedowneaster.com ) arrives at the Portland Transportation Center (100 Thompson’s Point Rd.) four times daily from Boston . Buses are operated from Boston  through Concord Coach Lines (100 Thompson’s Point Rd., Portland, 800/639-3317, www.concordtrailways.com ) and to the rest of New England through Greyhound (950 Congress St., Portland, 207/772-6587, www.greyhound.com ).
To drive to Portland, take I-95 to exit 44, then I-295 into the city. The drive is approximately 110 miles from Boston  (1 hr. 50 min.) and 50 miles from Kittery  (50 min.). For Freeport, continue north from Portland on I-295 to exit 15A (15 mi., 20 min.).
If you’re visiting sans vehicle, Portland’s  local bus company is Metro (114 Valley St., Portland, 207/774-0351, www.gpmetrobus.com , $1.25 adults, $1 students, free children under 5), which runs out of its downtown station to points that include the airport. Compared to most capital cities, Portland has a decent amount of metered street parking, which doesn’t guarantee you’ll find any right away (particularly in the summer), but the odds are good. That said, the city has pay lots and garages located every few blocks. Local taxis to call are ABC Taxi (207/772-8685) and Town Taxi (207/773-1711). In Freeport call Yarmouth Taxi (207/846-9336).