Portsmouth is the sort of place that tugs you back to visit again and again, a civilized little seaside city of bridges, brick, and seagulls -- and quite a lot of culture. Filled with elegant architecture that's more intimate than intimidating, this Boston-in-miniature projects a strong, proud sense of its local heritage without being overly precious about it. Part of the city's appeal is its variety: Upscale coffee shops and art galleries share main-street space with junk shops, barbers, tattoo parlors, and pierced local girls and boys. The upscale crowd has begun steadily elbowing old-time businesses out of the main square, but despite the influx of new money lately, this town retains an earthiness that serves as a great balance to more touristed and, well, saccharine coastal towns. Portsmouth's humble and historic waterfront is so understated that you actually have to seek it out; it's still a working waterfront, as you'll learn if you manage to locate it.

This city's history runs deep, a fact that is evident on even a quick walk through town. For the past 3 centuries, Portsmouth has been the hub of the coastal Maine/New Hampshire region's maritime trade. In the 1600s, Strawbery Banke (it wasn't called Portsmouth until 1653) was a major center for the export of wood and dried fish to Europe. Later, in the 19th century, it prospered as a center of regional trade. Just across the Piscataqua River in Maine (so important a connection that there are four bridges from Portsmouth to that state), the Portsmouth Naval Shipyard -- founded way back in 1800 -- evolved into a prominent base for the building, outfitting, and repairing of U.S. Navy submarines. Today, Portsmouth's maritime tradition continues with a lively trade in bulk goods; look for the scrap metal and minerals stockpiled along the shores of the river on Market Street. The city's de facto symbol is the tugboat, one or two of which are almost always tied up in or near the waterfront's picturesque "tugboat alley."

Visitors to Portsmouth will discover a surprising amount of available experiences in such a small space, including good shopping in the boutiques that now occupy much of the historic district; good eating at many small restaurants and bakeries; and plenty of history to explore among the historic homes and museums set on almost every block of Portsmouth.