Portland, Maine Vacation Guide

With stunning views across the waters of Casco Bay, sitting between the soft sand beaches of Maine’s southern coast and the rocky shoreline of Maine’s midcoast, is the historic port city of Portland, Maine, a favorite Maine vacation spot.

A Portland, Maine vacation offers the vibrancy of modern urban life amid century-old buildings, cobblestone streets, and a working waterfront. Just a short drive from I-95, by way of 295 and Route 1, Maine’s largest city is easily accessible and is one of the perfect year-round Maine vacation spots. From a busy harbor to streets filled with art galleries, award-winning restaurants, and specialty shops into charming Victorian neighborhoods, the city of Portland, Maine shows great pride in what it has to offer.

Portland Maine at Night

Visit Portland, Maine just once, and you will see why – according to the Portland, Maine Chamber of Commerce website – the #1 “Top Reasons to Choose Portland, Maine“, is that it was named among the “top twelve surprising, thriving and emerging world travel destinations for 2024 by Frommer’s Travel Guides and Frommers.com.” And in June 2024, Portland was Travel and Leisure, America’s Best Cities for Summer Travel, #3 pick – in September 2024 was T&L’s #4 pick for America’s Best Cities for Fall Travel!

Portland, Maine Activities & Attractions

Whether you visit the city for a day trip, a weekend getaway, or a week-long vacation, you will find plenty of things to do in Portland, Maine for family fun, children’s activities, group events, and even for the days when the Portland weather calls for inclement conditions.

Portland, Maine museums

  • Portland Maine Museum of Art, the oldest and largest museum in Maine
  • Portland Harbor Museum with displays of the maritime history of Portland Harbor
  • Children’s Museum and Theatre of Maine, featuring interactive exhibits and family activities
  • Maine Narrow Gauge Museum with an operating railroad of authentic two-foot gauge equipment

famous Portland landmarks

  • Portland Observatory, offering beautiful views of Casco Bay
  • Wadsworth-Longfellow House, the boyhood home of poet Henry Wadsworth Longfellow
  • Tate House, built in 1755 for Captain George Tate
  • Old Port Exchange, 19th-century brick buildings housing specialty shops, restaurants and pubs

Cape Elizabeth and South Portland, Maine lighthouses

  • Spring Point Ledge Light, situated at the end of a granite breakwater in South Portland
  • Portland Head Light, on Cape Elizabeth, is Maine’s oldest lighthouse

Other fun activities for a Portland, Maine vacation…

diverse Portland, Maine shopping

  • Dozens of locally-owned boutiques and specialty shops offer Maine Made gifts and other unique items, in downtown Portland.
  • The Portland Maine Mall (Maine’s largest indoor shopping complex), and the Christmas Tree Shop Portland, Maine are just a short drive from the city.
  • A short drive north to Freeport, Maine and you can visit the flagship LL Bean Outlet and Freeport, Maine Outlets.

Portland, Maine tours

  • Downeast Duck Adventures is a 65-minute fully narrated tour of Portland, including an exhilarating stop directly in Casco Bay, aboard the Downeast Duck.
  • Portland Trolley Tour offers a 90-minute fully narrated excursion aboard the “Discovery” trolley.

Odyssey Whale Watch Portland MaineAnd of course, what spring, summer or fall, Portland, Maine vacation would be complete without a Casco Bay cruise aboard the aptly named Casco Bay Lines, which year-round ferries passengers, vehicles and freight between Portland and Peaks Island, Little Diamond Island, Great Diamond Island, Long Island, Chebague Island, and Cliff Island, or a cruise on one of the sightseeing or whale watching ferries, or Maine windjammers or schooners that dock in Portland Harbor.

If you’re still looking for more things to do on your Portland, Maine vacation…

At the day’s end, there is plenty of Portland, Maine nightlife and entertainment to be found in the many restaurants, bars, pubs, and dance clubs throughout the city.

Hotels in Portland, Maine

Quaint inns, inviting B&B’s, boutique hotels, well-known chain hotels, and budget motels, along with mom-and-pop budget motels, are plentiful, in and around the city of Portland.

Dimillo's Portland MaineAnd if your family would like extra room, Portland, Maine vacation rentals can be a cheap and affordable alternative.

Many of the Portland, Maine lodging accommodations are within easy walking distance to Portland attractions, restaurants and shops. Located in the heart of Portland’s Old Port District – a block back from the waterfront is the elegant Harbor Hotel, honored with the American Automobile Association (AAA) four-diamond distinction for six years in a row.

Also situated a few blocks from the waterfront, is the elegant and traditional Portland Regency Hotel and Spa, with “Old world luxury in Portland’s Old Port District”, and the Hilton Garden Inn, offering “fantastic views of Casco Bay and Portland’s working waterfront”. This chain hotel also has a property conveniently located near the Portland, Maine airport.

In the heart of the Portland’s arts district, the Eastland Park Hotel is surrounded by galleries, shops and museums, and just a short walk to the Old Port section, and waterfront activities.

And, also located close to the Old Port, the Art’s District, and the waterfront, is the home of “Greater Portland’s largest indoor hotel swimming pool” – the Holiday Inn by the Bay, Hotel and Convention Center.

Bed and breakfasts in Portland, Maine

If you prefer a bed and breakfast in Portland, Maine, several await you…

  • Fleetwood House Bed & Breakfast, an 1892 Colonial-style home with a wrap-around porch…
  • Morrill Mansion Bed & Breakfast, located one block from the Maine Medical Center in Portland, Maine, and three-quarters of a mile from downtown Portland.
  • And, the Wild Iris Inn Bed & Breakfast, in a historic neighborhood, a quarter of a mile from the Art’s District and less than a mile from the Old Port.

If you plan to be in town during slow periods, most Portland, Maine hotels offer fantastic off-season discount rates. When booking a hotel, be sure to ask about the vacation package and special deals!

Portland, Maine Restaurants

The restaurants in Portland, Maine have earned some serious bragging rights. A perfect special occasion restaurant for your Portland, Maine vacation may be…

Dimillo's Portland MaineThe 555 Restaurant (Five Fifty-Five), on Congress Street, which received Wine Spectator’s Award of Excellence in 2009, and where Chef Steve Corry was named Food and Magazine’s Top 10 Best New Chefs of 2007. But the 555 is not alone…

The Fore Street Restaurant in Portland, Maine was named Number 16 in Gourmet Magazine’s Top Fifty Restaurants of the United States in 2017, and in 2018, Chef-partner Sam Hayward was named Best Chef Northeast by the James Beard Foundation.

Chef Rob Evans from Hugo’s Restaurant was the winner of the James Beard Foundation Best Chef Northeast.

However, fine dining is not the only culinary excitement on a Portland, Maine vacation. Rising and falling with the tides, twice a day, is DiMillo’s Floating Restaurant, a converted car ferry – sitting directly in Portland Harbor on Long Wharf. From its dining room and outside deck the views are fabulous, and if lines at the door are any indication, so too is it’s “freshest seafood, choice cuts of beef and Italian fare” menu.

Head back onto firm ground and find yourself surrounded by dozens of International restaurants – featuring Asian, Japanese, Chinese, Thai, Indian, Greek, Italian, Latin American, Mexican and Spanish cuisine, American restaurants – specializing in steak and seafood, and other uniquely prepared appetizers, salad, dinner entrees, pizza houses, sandwich shops, fast-food and chain restaurants, bakeries, ice cream shops, and coffee houses.

You will not be hungry when it’s time for your Portland, Maine vacation to end!

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