Don’t let mammoth international tankers, towering cruise ships, and fishing boats scare you away from Portland Harbor. After all, it’s the largest, most diverse and interesting metropolitan area north of Cape Ann.

Spring Point Ledge Light marks the southern entrance to Portland Harbor.

Indeed, it’s Portland’s commercial roots that make arriving and tying up along the waterfront so easy. Take, for instance, the marina and floating restaurant known as DiMillo’s, a dominant presence on the harbor since the 1980s. Only in Portland could a 72-year-old retired car ferry become a focal point of dining and boating along a busy waterfront. That’s actually saying quite a lot when you consider how much of a boating and food mecca Portland has become in recent years.

Mariners who tie up at DiMillo’s learn quickly just how much the “Forest City” has to offer. Although Maine-grown wood products are no longer the city’s lifeblood, you could easily give Portland a new nickname: the “Foodie City.” Within a few blocks of DiMillo’s are at least half a dozen five-star restaurants—with an additional 20 or so four-star eateries. Wine bars, coffee houses, bakeries, street vendors, and even a few diners add to the city’s gustatory diversity and make visitors wonder if anyone in town ever eats at home.

OLD PORT, NEW SHOPS

For boaters, the nearest and most intriguing part of town is the Old Port District, a collection of ancient brick and granite buildings that once were concerned primarily with maritime trade and the shipment of goods to all parts of the world. Nowadays, boutiques, antiques marts and, yes, some tee-shirt-and-mug shops dominate the scene while you navigate the cobblestone streets and funky back alleys. The action here continues well after dark with all manner of bars, pubs and music-oriented clubs available.

By the way, if you want to drop off or pick up crew in the downtown area, there’s a public dock at Bell Buoy Park next to the Casco Bay Ferry Lines terminal on the State Pier. Tie-up limit is 10 minutes, so coordinate with your friends to optimize your time.

Farther uptown is the newer Arts District, anchored by the Portland Museum of Art at the corner of Congress and High Streets. Art galleries, smaller museums, and related shops cluster around the area, along with—you guessed it—more eateries, both upscale and modest. Nearby Monument Square harbors a wide variety of folks who are art projects themselves, running the gamut from buskers and jugglers to just tatted-up wanderers who mingle with a sizable office-worker population and lunch crowd.

ARTS AND ARCHITECTURE

If the art in architecture is appealing, look no farther than the West End neighborhood, just a little west and south of the Arts District. In its shady back streets, you’ll find grand mansions built by the city’s forest-products magnates of the 18th and 19th centuries. Greco-Roman, Italianate, Federal, “cottage” and Victorian styles are all handsomely represented.

The Portland waterfront has become a popular stop for private yachts and cruise ships.

Conversely, if you’re looking for boating-oriented Portland, head back east on Congress Street toward the Munjoy Hill district and the Eastern Promenade. Marked by the lighthouse-like tower of the Portland Observatory at 138 Congress Street, this area also features restaurants and shops, many with a more international vibe than elsewhere in Portland. Decidedly residential, Munjoy Hill also overlooks the park, playground and boat launch facility known collectively as the “Eastern Prom.” Scores of boats lie moored off the Eastern Prom, many of them owned by the park’s visitors.

LAIDBACK SOPO

Munjoy Hill is certainly low key, but to gain access Portland Harbor’s easiest-going area, cross over to the South Portland side and tie up at Spring Point Marina, part of the state’s largest pleasure-boat enterprise, Port Harbor Marine. From its facility in the shadow of Spring Point Light you can access all that South Portland has to offer, at a decidedly slower pace than the “big city lights” of Portland proper.

Perhaps the most attractive part of the South Portland waterfront is its Greenbelt Walkway, which runs along most of the city’s shoreline from the Spring Point Light area to well beyond the bridge linking Portland and South Portland. Along it are spectacular views, attractive parks, a shopping district and a swimming beach—and, of course, access to all types of restaurants. So, if you’re bringing your boat to Portland Harbor, you’d best ship an appetite.