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Top 30 Destinations by Personality Type
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Portland, Maine

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Personality Types that Like it Best

Did You Know … ?

  • Portland Head Light was commissioned by President Washington and is Maine’s oldest lighthouse (1791).
  • Poet Henry Wadsworth Longfellow grew up in Portland; his family home is the oldest structure in the downtown.
  • When Maine became a state in 1820, Portland was its first capital.
  • Portland was homeport for the U.S. North American Fleet during World War II.
  • The Mayflower’s Capt. John Smith named the Calendar Islands in Casco Bay, thinking they numbered 365 (there are 785).

Victoriana by the sea

As with many other towns and cities along Maine’s Atlantic coast, Portland draws leisure visitors who want to base themselves in a pretty place while they pursue vacation activities on and around the sea. Some also head inland to busy themselves with biking, hiking or other favorite land-based passions.

However, Portland is different from other coastal towns. With a population of around 65,000, it is a metropolis with a real business district, plus the range of dining, nightspots and cultural events that befit a city. It is Maine’s largest urban area and the state’s business and financial capital.

Portland also has its own particular history, which explains why its historic districts have a Victorian look to them. Occupied by English settlers beginning in 1632, Portland began to come into its own — as a commercial port and shipping center — about 150 years later, after the Revolutionary War. Not quite a century after that, disaster struck: A fire, ignited during July 4 celebrations in 1866, destroyed a great deal of the city. Portland was almost completely rebuilt in the Victorian era, and the building material was brick.

Adding to the scene is the redeveloped Old Port. Now designated the Portland Historic Waterfront District, it is more than pleasing to the eye; it is functional and loved by both locals and visitors for its artists’ studios, one-of-a-kind shops, eateries and pubs, located in former warehouses (also Victorian and brick).

Portland’s tourists like these attractions in combination with the natural charms of Maine’s outdoors. The city sits between forest-covered mountains and a picturesquely rugged coast. It boasts a deep and protected harbor on Casco Bay, which still serves commercial shippers as well as a large leisure clientele. Visitors come to hone sailing skills or take passage on vessels of all types, for fishing, for viewing historic forts, lighthouses and other coastline scenes, for watching wildlife and more. Some get closer to the water in a kayak, on waterskis or on a beach.

The primary focus for Portland’s active travelers is the sea, but those mountains and rugged coast are convenient and very alluring, too!

Things to do for Venturers

  • Get married in Maine, and make a lighthouse the venue. Seven of Maine’s 65 lighthouses are in the Greater Portland area. (Not all the state’s lighthouses are open to the public, however.)
  • Surf at Scarborough’s beach.
  • Sign on for an ocean sailing and ocean navigation course offered by the School of Ocean Sailing. You will live aboard your vessel for seven days. The courses are offered in Portland in summer (and in the U.S. Virgin Islands in winter).
  • Find your way around the nightspots that include entertainment. You may find bluegrass, hip-hop, jazz, reggae or rock — or all of them.
  • For an unusual approach to sightseeing, board the mail boat, operated by Casco Bay Lines, to see Portland’s island communities.
  • Paddle a kayak or canoe at Sebago Lake about 30 miles west of Portland. Or if you would rather, waterski on the lake.

Things to do for Centrics

  • Take a commemorative walk along Portland’s Freedom Trail, which encompasses more than a dozen marked sites associated with the Underground Railroad and the state’s anti-slavery movement.
  • Eat lobster as often as you like. But you are not limited to seafood. Consider trying locally produced elk or venison.
  • Greater Portland boasts a network of recreational trails that hug the waterfront and traverse the woods, too. In winter, follow the trails on cross-country skis; in warmer seasons, make that hiking or biking.
  • Take a guided tour designed for food lovers. You will learn and taste what is special about Portland as a culinary destination.
  • Join lobstering excursions on Casco Bay between Memorial Day and Columbus Day and participate in hauling up lobster traps. Sailings also take passengers past rocky shore areas where seals sun themselves.
  • Sail aboard a windjammer from the Maine State Pier in Portland. You could go to sea for as little as two hours or for overnight cruises. Or, if you want more action, go deep-sea fishing instead.

Things to do for Authentics

  • Take the time to savor the charms of Portland’s Old Port, the historic waterfront area. Walk the cobblestone streets, eat fresh foods in fine restaurants, drop by the brew pubs, shop in the boutiques — and inhale the salty air.
  • To see the epitome in elaborate Victorian architecture and interior design, visit the Victoria Mansion, which dates from 1860.
  • Play golf at an area course. Enjoy the scenery, which may be mountains or the sea.
  • Plan a self-drive sightseeing tour of Greater Portland. Make the area’s seven lighthouses the theme.
  • Shop for Maine specialty foods such as chocolate-covered blueberries and smoked seafood, but if the shopping urge is really out of control, pop over to Freeport for a day in the outlets.
  • Join the fun and sample the goods at Portland’s Harvest on the Harbor, a three-day celebration of local foods, wines and spirits, set for October.

Additional Resources

For more information, consult the Greater Portland Convention and Visitors Bureau at