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AARP’s City Guide to Portland, Maine

Waterfront lodging and a love for lobster help reel visitors in to this seaside gem

spinner image Left, the skyline of Portland, Maine. Right, the Portland Head Light
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Portland, Maine, regularly appears on lists touting the best places to live, play and eat. This smaller port city (population 68,000) edging island-salted Casco Bay entices visitors with its local food scene, lively waterfront, art and architecture, history, walking and biking trails, as well as Maine’s holy trilogy: lobster, lighthouses and L.L.Bean. 

When to go to Portland

Portland hums year-round. May through October is peak season, when rates for accommodations rise and advance hotel and dinner reservations are a must. Weather is predictably unpredictable, and fog can turn a brilliant summer day into a chilly one quickly. Snow and/or icy rain are possibilities from November into March. 

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How to prepare for your trip

Make reservations for lodging, restaurants and tours, especially during peak season and on weekends year-round. Portland’s downtown peninsula is a hill. Many of its sidewalks are brick and many buildings date from the Victorian era and have entry steps. While larger and newer accommodations are ADA compliant, smaller or older inns and other businesses often are not and many lack elevators. Pack good walking shoes, a raincoat and umbrella, hat, a sweater or fleece and seasonal wear (boots, hat and gloves in the winter). 

spinner image A woman riding a ferry out of Portland, Maine
Multiple companies provide ferry rides and water taxis to islands around Portland.
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How to get to Portland

Portland is easily accessible by car. ADA-compliant Concord Coach Lines offers the best bus connections from Boston’s South Station (about an hour and 40 minutes) and all terminals at Logan Airport to the Portland Transportation Center. Amtrak’s ADA-compliant Downeaster train travels to Boston’s North Station and offers a 50 percent discount on most trains for passengers 65 and older. Major airlines, including JetBlue and Southwest, fly into Portland International Jetport. The Greater Portland Transportation District’s ADA-compliant Metro bus Route 5 connects the airport and transportation center with downtown Portland; Route 8 loops the downtown peninsula. Taxis and rideshares are available, and some hotels offer free shuttles. While it’s easy to get around the downtown peninsula on foot, its promontory location means going up and down the hill. Brick sidewalks may also be a challenge for those with mobility disabilities.

Where to stay in Portland ​

An 1881 brick building designed by architect Frances Fassett morphed into The Francis, a 15-room boutique hotel, in 2017. The renovation preserved period details without sacrificing contemporary amenities. The minibar features locally made products. Tip: Reserve directly with the hotel to score free parking.

Built around a garden courtyard, the Portland Harbor Hotel puts the city’s Waterfront and Old Port within footsteps. The 103 guest rooms and suites have a jaunty nautical style. Suites in the executive wing include fireplaces. Perks include a comfy lounge, a restaurant, a fitness center and an outdoor fire pit. Valet parking in the hotel’s garage is $40 per night.

The eight-room Spring Point Inn on Southern Maine Community College’s waterfront campus is about 10 minutes from downtown Portland. The location puts Willard Beach, two lighthouses and Fort Preble’s ruins within walking distance along the Spring Point Shoreway. Most rooms overlook Portland Head Light, Spring Point Ledge Lighthouse or the Portland skyline. Other perks: continental breakfast and parking are free. ​

From downtown, it’s about a 15-minute drive to the beachfront, eco-conscious Inn by the Sea in Cape Elizabeth. This luxury boutique inn offers rooms and one- and two-bedroom suites. Sustainable, chemical- and pesticide-free gardens emphasize indigenous plants and are certified as a Monarch Watch butterfly way station. And the inn has restored the landscape between the property and the beach as a rabbit habitat to help the endangered New England cottontail. Parking is free. 

Notable chain hotels include the Westin Portland Harborview, with a rooftop lounge offering panoramic views of the water; the AC Hotel by Marriott Portland Downtown/Waterfront Portland is two blocks from the shopping and restaurants in the Old Port District; and The Press Hotel is a Marriott property in the former home of the state’s largest newspaper. 

spinner image The Portland City Hall clock tower in Portland, Maine
The grand City Hall building is located in downtown Portland.
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Things to do in Portland 

Victorian Masterpiece: Don’t judge the Italianate Victoria Mansion by its brownstone exterior. Inside, it’s a jaw-dropper. The National Historic Landmark retains 90 percent of its original interior, including most of designer Gustave Herter’s original furnishings, murals, gilded glass chandeliers and a mahogany flying staircase. Allow one hour for the guided tours ($19.25 for adults, $17.25 for ages 62 and older), departing every 20 minutes May 1-Oct. 31. It reopens for self-guided tours from late November to early January, when it’s lavishly decorated for the holidays. 

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Get Real: On the 90-minute The Real Portland Tour, Portland native and college librarian Derek Meader introduces you to the best of this seaport city. His van tours explore downtown sights including the Portland Observatory, poet Henry Wadsworth-Longfellow’s childhood home and the Eastern Promenade seaside park. And then it loops out to the burbs to view Portland Breakwater Lighthouse, the Liberty Ship Memorial, Spring Point Ledge Lighthouse and Portland Head Light. Meader’s entertaining tour includes historical trivia, quirky tidbits and fun facts, along with his insider insights ($55 for adults; $53 for ages 65 and older). 

Local Brewhaha: Maine vies with Vermont for the title of most craft breweries per capita. Greater Portland has an increasing number of distilleries, wineries and kombucha, mead and cider producers. Dive into the scene on an all-inclusive, guided Brews Cruise tour. Options include a 1.5-mile walking tour, a leisurely 3-mile bicycle tour or a half-dozen bus tours (tours start at around $75). 

Woods and Water: Thanks to the nonprofit organization Portland Trails, more than 70 miles of pedestrian and multi-use trails thread together the Greater Portland area. Explore the 85-acre Fore River Sanctuary, home to Jewell Falls and a lowland marsh where saltwater meets freshwater and the former Cumberland and Oxford Canal. Or walk through Baxter Woods, a 30-acre nature preserve, and 239-acre Evergreen Cemetery and woodland. Both also offer good birding during spring and autumn migration. For winter explorations, rent snowshoes from Gorham Bike & Ski.

Pedal Power: Rent a road, hybrid or electric hybrid bike from Cycle Mania and zip around Portland Trails’ Back Cove, Eastern Promenade and Harborwalk trails. Then ride across the Casco Bay Bridge to South Portland’s Greenbelt Walkway to visit Bug Light Park and the Liberty Ship Memorial. Still energized? Continue along the Spring Point Shoreway to Spring Point Ledge Lighthouse and Willard Beach.

spinner image A lobster roll from Portland, Maine
Maine is known as the Lobster Capital of the World.
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Where to eat in Portland 

Chef Sam Hayward earned a reputation for farm-to-table fare in the early ’90s and brought that locally and sustainably farmed, fished and foraged philosophy to his restaurant Fore Street in 1996. Hayward put Fore Street and Portland on the food map when in 2004, he earned Maine’s first James Beard Best Chef Northeast award. Today, the bi-level dining room provides a view of the open kitchen. The restaurant’s heart is the brick-and-soapstone hearth, with a wood-burning oven, grill and turnspit. The dinner menu changes daily. 

Third-generation Maine lobsterman Luke Holden opened his first lobster shack in New York City in 2009 but Luke’s Lobster on the Portland Pier brought it home. Feast on panoramic views over the working waterfront from the two-story restaurant’s dining room and outdoor tables. Keep an eye out for seals, and watch ferries and lobster boats unload their catches at Luke’s adjacent buying station. While lobster is the star, you’ll find other options including popcorn chicken. Well-behaved dogs are welcome at outdoor tables. 

spinner image DiMillo's on the water boat restaurant in Portland, Maine
DiMillo’s on the Water floating restaurant serves fresh seafood and homemade blueberry cobbler.
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Drink in the views while feasting aboard a ferry to nowhere at DiMillo’s on the Water. DiMillo’s history dates back to 1954, but it wasn’t until 1980 that the DiMillo family purchased The New York, a former car ferry, and renovated it as a floating restaurant. DiMillo’s American menu highlights seafood, but burgers, steak and chicken preparations are available. And here’s a plus: Parking is free while dining at DiMillo’s.​

American comfort food fills the menu at Becky’s, a classic waterfront diner on Hobson’s Wharf that serves breakfast, lunch and dinner daily. Slide into a red-vinyl-and-wood booth or request a seat on the upstairs deck and enjoy a much-lauded lobster roll.

Step in the European countryside at Chaval, a neighborhood brasserie in the city’s West End. Damian Sansonetti’s seasonally inspired fare draws from French and Spanish influences. Cobble together a meal from small plates or choose one of the Fork & Knife dishes, such as the classic coq au vin. Whatever you do, order one of pastry chef Ilma Lopez’s swoon-worthy desserts. The Spanish ice cream made with smoky serrano ice cream, caramel and chocolate cake is divine. If the weather’s fine, request a table on the outdoor patio. 

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Art and Architecture: Here’s a double treat. First, the Portland Museum of Art boasts works by American and impressionist masters along with fine and decorative arts in three interconnected buildings: the beaux arts, John Calvin Stevens-designed L.D.M. Sweat Memorial Galleries; the restored Federal-style McLellan House; and the Charles Shipman Payson Building, designed by Henry Nichols Cobb of I. M. Pei & Partners ($18 for adults; $15 for seniors). Among the treasures are works by Winslow Homer, who painted many of his masterpieces at nearby Prouts Neck. And second: Reserve well in advance to visit the museum-owned Winslow Homer Studio, which opened after a meticulous, six-year renovation restored it to how it appeared during the artist’s life. The guided 2.5-hour tours depart from the museum and include transportation ($65 per adult); the maximum capacity is 12 people.

Ways to save: Museum admission is free from 4-8 p.m. on Fridays. Save $10 off tours of the Winslow Homer Studio in the offseason starting Oct. 19. ​

Lobster 101: After cruising Portland Harbor with the Lucky Catch lobster tour, you’ll be able to regale friends and family with facts and lore about Maine’s tasty crustaceans. During the lobster boat tour, which runs 80-90 minutes, you can help haul traps and process what’s inside ($50 for adults). Along the way, you’ll view islands and lighthouses. And here’s the clincher: Any lobsters caught are available at boat price, and a nearby lobster shack will prepare them for a reasonable fee.

Ways to save: For an inexpensive way to see lobster boats working on the water, hop aboard the Casco Bay Lines Mailboat Run. The 2.5- to 3.5-hour cruise carrying passengers, freight and mail visits five islands ($17 for adults, $14.50 for seniors). 

Shop ’til you drop: Travel 20 minutes north of Portland to shop at L.L.Bean’s flagship store in Freeport. Bean’s empire began when founder Leon Leonwood Bean created duck boots and sold them with a money-back guarantee. Now you can find anything from pajamas and sheets to hunting and fishing equipment. For more shopping, check out the independent shops and brand outlets including Coach and Old Navy in Freeport Village Station, across the street from L.L.Bean. 

Ways to save: The L.L.Bean Outlet store is one of the shops in Freeport Village Station, and you may be able to find a deal on something similar to what you were eyeing in the flagship store. 

Island time: Cruise to Peaks Island, 20 minutes from Portland’s waterfront, aboard a Casco Bay Lines ferry for an interesting day trip. The easiest way to see the island is on a 75-minute golf cart tour with Peaks Island Tours ($25 for adults, $22 for ages 65 and older). At the tiny, quirky, Guinness World Record-holding Umbrella Cover Museum, director Nancy 3. Hoffman ends tours by singing “Let a Smile Be Your Umbrella” while playing her accordion. Civil War vets built two lodges here: the Fifth Maine Regiment Center, recognized on the National Register of Historic Places, and the 8th Maine Oceanfront Lodge & Museum, constructed by a member with winnings from the Louisiana lottery (both open in late May/early June). Bring a flashlight if you want to prowl around Battery Steele, a National Historic Register World War II battery. The ferry departs from the Casco Bay Lines terminal ($7.70 for adults; $3.85 for ages 65 and older).

Ways to save: Ferry rates drop to $4.10 for adults, $2 for seniors after Oct. 9.

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