Portland, Maine

Portland Head Light. Photo Tom Richardson

Don’t let hulking fuel tankers, ferry boats, cruise ships, and other large vessels scare you away from Portland Harbor. Indeed, it’s Portland’s commercial roots that make arriving and tying up along the waterfront so easy. Take, for instance, the floating restaurant and marina known as DiMillo’s, a dominant presence on the harbor since the 1980’s. Only in Portland could a 72-year-old retired car ferry become a focal point of dining and boating along a busy waterfront.

Portland frequently welcomes large yachts. Photo Joe Devenney

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.” The compact downtown contains at least half a dozen five-star restaurants. 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.

Resident boaters enjoy the evening at DeMillo’s. Photo Tom Richardson

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, making one wish that Portland proper made more of an effort to welcome recreational boaters. That need has recently been assuaged by the opening of the Fore Points Marina on the city’s East End. The full-service marina, part of a larger development to include housing, shops, and even more restaurants, welcomes transients and can accommodate vessels of virtually any size.

Dining options abound in and around Portland. Photo Tom Richardson

Arts & Architecture

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 in themselves, running the gamut from buskers and jugglers to just tatted-up wanderers who mingle with a sizable office-worker population and lunch crowd.

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. Amid 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 in a district still devoted to the city’s most elite citizens.

A lobster boat passes in front of Fort Gorges. Photo Tom Richardson

Conversely, if you’re looking for middle class and 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 a bit more ethnic than elsewhere in Portland. Decidedly residential, Munjoy Hill also overlooks the park, playground and boat launch facility known collectively as the “Eastern Prom.”

Sea kayaking is a great way to explore Casco Bay. Photo Tom Richardson

Laidback SoPo

If you’re looking for Portland Harbor’s more easiest-going neighborhood, cross over to the South Portland side (for details, visit the South Portland destination section) and tie up at Spring Point Marina, part of the state’s largest pleasure-boat enterprise, Port Harbor Marine. From its facility in the shelter of Spring Point Light you can access all that SoPo has to offer, at a decidedly slower pace than the “big city lights” of Portland proper.

The downtown area boasts interesting sculptures and architecture. | Photo by Joe Devenney

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.

If you’re bringing your boat to Portland Harbor, you’d best pack an appetite!

The Eastern Prom features a good public launch ramp.

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