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.
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).
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.