Ideally, a vacation to Maine would be leisurely and lengthy, but even a short visit can show off the charms of this New England state. Reason No. 1 to make the trek: natural beauty. Thousands of miles of coastline, dramatic cliffs, 3,000 islands, and the fact that 90% of the state is covered in trees. Reason No. 2: The towns. So many look like something out of a movie set, filled with tree-lined main streets, coastal architecture, and walkable downtowns. The food scene in Maine merits its own category — and not just because of lobster rolls. Then there’s the convenience factor for those of us in the Southeast. A flight to Portland is shorter than somewhere out west, and you don’t have to deal with significant time-zone changes.

Time of year plays an important role, however. Small towns like Bar Harbor pretty much shut down during the winter, with not much open until Memorial Day, then slowing down at the end of the season in October. Summer months are packed with visitors (and more expensive), however, so you pay a price for warmer weather.

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This Instagram-perfect sight is just minutes from the Portland airport, so it’s easy to get a quick fix of lighthouse and cliffs within 24 hours of landing. The Portland Head Light has 90 acres of park land around it, perfect for walking and catching some ocean breezes. Four other lighthouses can be seen from the high vantage point.

Day 1

Fly into Portland, Maine, the state’s biggest city. Flights from Atlanta are only about 2.5 hours, so a morning arrival allows for time to explore. Rent a car and stash your bags at The Press Hotel (rooms from around $400 in high season, lower other times of the year), a cool boutique hotel reimagined from the former offices and printing press of the city’s newspaper, the Portland Press Herald. References to the newspaper and written word are a visual delight everywhere — from the wall art made of vintage typewriters, to wallpaper on the hallways filled with newspaper phrases from over the years.

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Wall art in the lobby made from vintage typewriters is just one cheeky reference to The Press Hotel’s former function. The downstairs level is devoted to an art gallery of local works. Image: The Press Hotel

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Test your typing skills on one of the several old-school typewriters located throughout the lobby.

Another great hotel option is Cliff House Maine, located about an hour north of the Boston airport. The 145-year-old resort stretches along 70 beautiful oceanfront acres, giving guests unbeatable views of both the surrounding waters and the Nubble Lighthouse. Guest room acommodations include spacious showers, a private terrace, Serta Signature Suite Elite II mattresses, and goodies from Red Flower — a small-batch beauty and wellness company. Plus, be sure to visit the resort’s on-site spa, which offers massages, body wraps, hair and scalp treatments, body cupping, and more.

Aerial view of Cliff House Maine

Just an hour north of Boston’s airport, the Cliff House Maine resort has been drawing visitors for over 100 years to experience its dramatic cliffs, award-winning restaurants, and hotel rooms where every room has an oceanside view. Image: Cliff House Maine

Lounge at Cliff House Maine

Floor-to-ceiling windows in the lounge at Cliff House Maine offer an ideal place to start the day with coffee or end it with a nightcap. Image: Cliff House Maine

Once you’re settled in, it’s time to explore the harbor’s cobblestone streets filled with businesses, stores, and restaurants along the way. Stop in at The Holy Donut, a beloved Maine destination selling imaginative donuts made from local potatoes. If you’re not too full after that, it’s time to check off “lobster roll” (or, as the locals say, “lobstah roll”) on your to-do list. Yes, it’s a little touristy, but you can’t beat the wharf-side Portland Lobster Company for all things lobster — as well as crab cakes, clam chowder, and shrimp wraps.

Walk off the food on the East End part of town — adjacent to historic downtown — where bookstores, breweries, and other entrepreneurs have set up shop. You might pass innovative shopping in old shipping containers at The Black Box, enjoy some locally made coffee at Tandem Coffee, or taste a flight of locally foraged kombucha at Urban Farm Fermentory. When it’s time for dinner, head back downtown to try any number of nationally recognized restaurants. We liked Central Provisions, a recent James Beard finalist for the best new restaurant in the nation. Its small-bites menu made of just-picked ingredients offers a good opportunity to sample locally sourced cuisine.

maine vacation

Cobblestone streets line the downtown area of Portland. Central Provisions — now a well-known restaurant recognized with a James Beard nod — dates back to 1874, when it was used to store silk, salt, tea, and opium.

maine vacation

Maine has brutal winters, but from late May through October, residents and visitors savor the outdoors, and restaurants embrace al fresco dining. Portland Lobster Company is the place to people watch and enjoy one of the seafood specialties.

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When in Maine, eat a lobster roll! These buttery buns with chunks of fresh-caught lobster are everywhere in the state.

Day 2

Enjoy a hearty breakfast at the hotel, then hit the road for a 12-minute drive to Cape Elizabeth to take in the Portland Head Light. This picture-perfect lighthouse surrounded by craggy cliffs and crashing waves is an ideal place to walk around. A one-mile cliff walk offers varying views of the lighthouse (and others nearby), as well as charming houses perched on the cliffs and dog-friendly parks.

Head north to the Rockland-Camden area, breaking up the journey to Acadia National Park with a stop in these two quintessential New England towns. Rockland is known for its arts community (there are plenty of places to stop along U.S. 1 for artisans, antique stores and pottery places), including the Farnsworth Art Museum, a well-regarded place to see Winslow Homer, Edward Hopper, Andrew Wyeth, and other icons of American art. Stop in at Sea Bags, a Maine company known for its tote bags and pillows made from recycled sails.

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All sorts of wares made from recycled sails fill the store Sea Bags in Rockland (with several other locations in the state).

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The “Eat” sculpture by artist Robert Indiana delineates the Farnsworth Art Museum in Rockland, Maine. The small town is a good lunch stop.

Check in to Samoset Resort (rooms around $350 in high season), a historic property along the coast with picturesque views of Penobscot Bay and Rockland Breakwater lighthouse, for a one-night stay. Before dinner, take the mile-long boulder walkway to the lighthouse itself and enjoy the quiet views. You’ll probably see a lobster fisherman checking his traps while there. Then drive the 10 minutes or so to Camden for another small-town experience. Don’t miss the award-winning cuisine at Long Grain, a locavore Asian restaurant … it’s where the locals — and top newspaper restaurant critics — eat.

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The innovative — and always changing — menu at Long Grain restaurant in Camden might include something like this refreshing papaya/green bean/dried shrimp salad. All dishes are served on vintage china.

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maine vacation

Tucked behind the golf course on Samoset Resort’s property is the walkway to Rockland Breakwater lighthouse.

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Views from the Samoset Resort include the property’s pool, golf course and the lighthouse itself. Image: Samoset Resort

Day 3

Grab a quick breakfast at Camden’s The Owl & Turtle Bookshop and Café and savor this wood-lined independent bookstore while enjoying a specialty coffee and home-baked muffin. Pop around the corner to see Camden’s waterfall and marina, as well as those lucky houses with harbor views.

It’s about a two-hour drive to Acadia National Park, but even the journey is relaxing thanks to all the coastal sights and small towns along U.S. 1. Head straight to Jordan Pond House in Acadia, the park’s only restaurant — and a treat itself for the famous popovers and blueberry lemonade. Afterward, you don’t have to go far for a quintessential Acadia experience. The 3.5-mile pathway around Jordan Pond is scenic and a popular way to experience that unique combination of mountains, spruce trees, and clear water with seagulls flying overhead. A park ranger outside the restaurant can recommend other more challenging hikes.

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You can’t get much more charming than this small-town bookstore/café in Camden, The Owl & Turtle.

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Inside The Owl & Turtle, two stories of books, tucked-in places to relax, and a small coffee shop make this a worthwhile stop.

maine vacation

Stunning views at Acadia National Park include the area around Jordan Pond, with its conifers and clear waters.

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Acadia is the only national park in New England, which is one reason for its popularity. It’s also full of natural riches: There aren’t many places on the east coast to see a rugged coastline and tree-lined mountains together.

The quaint town of Bar Harbor, just outside Acadia, will be home for the next two nights (but even one night could give you a taste). Check in to The Harborside Hotel (rooms from the $400s in high season) on the ocean in downtown Bar Harbor for a convenient and comfortable headquarters. Two oversized sofas in front of the lobby fireplace are an excellent place to plan the day — or talk about it afterward.

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Newly renovated rooms at The Harborside Hotel in Bar Harbor feature the same beautiful coastal views out the window, but now with fresh nautical décor. Image: The Harborside Hotel

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Downtown Bar Harbor has some touristy stores, but authentic ones, as well, including shops devoted to local artisans and mom-and-pop coffee places.


Day 4

There are so many options for how to spend a day here. Acadia National Park has some must-see, jaw-dropping spots within the park: high up on Cadillac Mountain (a favorite for sunrise and sunsets), or along the coastline at Thunder Hole or Sand Beach. Also, be on the lookout for the 17 stone bridges throughout the park.

Back in Bar Harbor, boat trips include whale-watching tours, lighthouse jaunts, and trips to see puffins. The town itself is popular for strolling, shopping, and relaxing in parks, although it can get crowded and a bit touristy. Wander off the main streets and find some hidden gems.

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maine vacation

Even a rainy day at Acadia is better than regular life. People love the drama of Thunder Hole, with its crashing water feature and angular cliffs.

Day 5

If you’ve booked a late afternoon or evening flight, it’s possible to get in one more outdoorsy experience — maybe a walk around nearby Eagle Lake in Acadia, or just strolling the harbor in town. The drive to Portland is only about 3.5 hours, so it’s convenient to make a visit to Freeport for the L.L. Bean flagship store, which is more of a compound with multiple stores (we liked the L.L. Bean Home shop), anchored by a giant hiking boot. Next stop: Returning the rental car and heading home, but we promise you’ll already be mentally planning your next visit to Maine.

All photos by Lisa Mowry unless otherwise noted.


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