Settled in 1623, Portsmouth lays claim to the title of third-oldest city in the nation, but at 21,000 inhabitants, it’s no metropolis. And that’s just fine. With a rich fishing, shipping and brewing past, and a still active working port, Portsmouth and its pleasures are smaller scale. They’re also best approached on foot. Visitors will find no end of brick sidewalks to stroll, boutiques to pop into, and Colonial, Federal and Georgian houses to tour. Then there’s the food: Portsmouth is blessed with an absurd selection of restaurants, cafes and ice cream parlors to ponder. After a long day’s shopping, gallery hop or boat ride, visitors seem to end up at a new favorite waterfront watering hole. Once installed at the bar or patio, raise a mug of frosty ale to this surprising little city of contrasts: touristy and local, cultured and blue collar, historically preserved and scrappy.

FRIDAY

2:30 p.m.

1. Walkabout

Ditch the car, and get the lay of the land as a pedestrian. Portsmouth’s historic core of brick and clapboard buildings radiates from Market Square, the city’s ground zero, along Congress, State, Daniel, Pleasant, Bow and Penhallow Streets. For a shot of orientation, head away from the waterfront to the fancy welcome center called Discover Portsmouth. Here, procure a map for your wanderings, peruse the museum shop, watch the short film covering the city’s history, perhaps listen to a historical talk or take in an art show.

4:30 p.m.

2. Book Hop

Portsmouth’s newest innovation is Book & Bar, housed in the granite Old Custom House and Post Office building, originally constructed in 1860. The establishment sells a mix of new and used books, plus the de rigueur coffee drinks. Book & Bar also offers light fare like a pesto and Parmesan pressed sandwich ($8) or polenta triangle with caponata ($7). And you can grab a glass of wine or beer, including pints like White Birch Belgian Style Pale Ale ($7). A couple of blocks away are two other fine indie book stops: RiverRun Bookstore, for a solid mix of new and used, and Sheafe Street Books, for gently read tomes shelved under categories like “Donald Hall” (the New Hampshire writer) and “submarines.”

6 p.m.

3. Harbor Life

Looking for a bar with a view? Thankfully, the city has reclaimed public access to its waterfront. At the confluence of Ceres and Bow Streets, stop at the newly built picnic area and admire the tugboats, then take a footpath to the right of the Old Ferry Landing restaurant. Pass the wooden patios of a couple of other drinking spots and arrive at Martingale Wharf (on the site where sailors and ladies of the evening once caroused). Grab a seat on the patio, sip a concoction like the Riverwalker (gin, grapefruit juice, Lillet and orange bitters, $9), and take in the vista of bridges, salt piles and tugs and tankers plying the Piscataqua River. If it’s chilly, grab a blanket and snuggle by the fire pit.