The Old Port, Portland, Maine

Did you know that Portland has more dining spots per capita than any other city in America? And many of them are nestled into the area of the city fondly called the Old Port. The Old Port is Portland’s revitalized warehouse district. Cobblestone streets span the waterfront, offering oceanfront dining, entertainment, and chic shopping opportunities. Yet the Old Port is also a working waterfront, which provides visitors with a taste of real Maine.

Dining options abound in the Old Port. For an original fine-dining experience, Five Fifty-Five, located at 555 Congress Street, is the area’s high end, award-winning restaurant, specializing in local, organic ingredients.

If you’d like to eat on the ocean, literally, try DiMillo’s Floating Restaurant. What was once a car ferry is now a restaurant that rises and falls with the tide each day. Every table in the restaurant offers water views, but DiMillo’s is famous for more than its views. They are also well known for their Admiral’s Portion of Lazy Lobster!

For affordable, authentic, and delicious Mexican fare, visit Amigos, on Dana Street. Or if it’s authentic Italian you crave, visit Cinque Terre on Wharf Street, the area’s leading Italian restaurant. Or, if you are in the mood for an exhaustive wine list and exquisite desserts, be sure to check out The Wine Bar on Wharf Street, one of the finest places to relax in the entire city.

For those who want to embellish in luxurious and stylish lodging, The Danforth Hotel has been welcoming visitors for nearly two hundred years. Another popular destination is Portland’s new downtown luxury hotel, the Portland Harbor Hotel, which is located right in the heart of the Old Port. And the Holiday Inn by the Bay is only a few blocks from the Old Port, offering rooms with ocean views.

If possible, plan your visit to coincide with Portland’s First Friday Art Walk. On the first Friday of every month, from 5 to 8 p.m., Portland’s art galleries open their doors to the public, while other artists exhibit work in the backs of pickup trucks. Design your own self-guided tour and watch local performance artists dazzle the streets of Portland. If you can’t make it for an art walk, be sure to visit Aucocisco Galleries, a contemporary fine art gallery located in the heart of the Old Port. This renowned gallery is open Tuesday through Saturday, from 11 to 6.

Many attractions are packed into the Arts District of Portland. Visit the Portland Museum of Art, which is home to a permanent collection of paintings by Winslow Homer, Renoir, Degas, Monet, and Picasso. Check out the Maine Historical Society and adjacent Longfellow House. Families adore the award winning Children's Museum of Maine. Or see what’s happening at Portland Stage Company.

Parking is sometimes a challenge in the Old Port, as the old streets are narrow, especially in winter, when vehicles have to compete with snow. Many downtown businesses offer parking stamps, which cover one hour of parking in many garages and lots, so be sure to ask, and collect those stamps! In the summer months, several bike racks are available. Many people choose to leave their cars at the hotel, and explore the Old Port the old-fashioned way, on foot!