Exploring Portland, Maine: An Insider’s Journey

I first started visiting Portland regularly a little over 10 years ago, taking the quick trip north from Boston every spare weekend I could. Well regarded as a culinary hot spot that’s soaked in seaside charm, the easily walkable city is the perfect place to spend a long weekend—or more. From the cobblestone streets of the Old Port to beloved local haunts on Washington Avenue and the West End, it’s easy to feel at home here instantly, while still sometimes experiencing it like a tourist.

Best Hotels & Resorts

Longfellow Hotel

Longfellow Hotel is not only situated in the heart of one of Portland’s best neighborhoods, the West End, but it’s also relatively large by the city’s standards. If you need another reason to book, though, the property is just a stone’s throw from Tandem Coffee + Bakery, putting you at a distinct advantage to be first in line for one of their legendary breakfast sandwiches. The 48-room boutique hotel has a focus on wellness, housing an on-site spa with private infrared saunas and guest rooms designed for a great night’s rest.

The Francis

The Francis is a small boutique property from the same team behind the Longfellow Hotel, Uncommon Hospitality. It’s housed in a building from 1881, and each of the 15 rooms has its own unique charm. Like all historic properties, it has some quirks. While the free parking and included breakfast are big perks, one of the hotel’s best features is that it shares a building with Wayside Tavern, a top restaurant in the city. Finn Naylor, marketing director at Rosemont Market & Bakery, says, “Wayside Tavern is at the top of my list. Their food is always seasonal and thoughtful, the wine list is excellent, and the vibe is unfussy in the best way.”

The Docent’s Collection

If you’ve ever wanted to try living in one of downtown Portland’s best neighborhoods, the Old Port, this is the place to do it. The Docent’s Collection offers a handful of loft-style apartments, complete with kitchens. Jordan Nugent, director of travel and events with Experience Maine, says, “I love The Docent’s Collection because it feels more like apartments, each with its own kitchen and living area, located in the heart of the Old Port. It’s great for larger groups traveling together or longer stays.”

Blind Tiger

Blind Tiger is made up of two historic buildings in Portland’s West End. When traveling throughout New England, I always go out of my way to see if there’s a Lark Hotels property nearby. No two rooms are ever identical and each location is engrained in its individual neighborhood, with Blind Tiger being no different. The property offers a complimentary light breakfast, and free parking and ample (and comfortable) public space on the first floor make it easy to linger between jaunts to one of the many amazing restaurants and bakeries in the neighborhood.

Press Hotel

The Press Hotel is in downtown Portland, operating in the historic headquarters of the Portland Press Herald. The 110-room property, operated by Marriott, has a boutique feel and welcome amenities such as valet parking and room service. Don’t skip out on breakfast at Union, where you’ll contemplate where blueberry breakfast sausage has been all your life.

Best Things to Do

Visit Fort Williams Park.

Take a quick drive over to Cape Elizabeth and stroll through Fort Williams Park. Roughly 15 minutes from downtown Portland, the park spans more than 90 acres, with dramatic cliffs and the iconic Portland Head Light. Pack a picnic lunch or grab one of the city’s best lobster rolls from Bite Into Maine.

Get on the water.

The best way to appreciate the beauty of Portland is to see it from the water, and luckily, there’s no shortage of ways to do it. Nugent says, “Get out on the water when the weather is nice. We have so much access to neighboring islands and boat tours.” You can enjoy a wine tasting aboard a sailboat with Wine Wise Wine Sails, see how lobsters are caught with Lucky Catch, hop on a low-key sunset lighthouse tour with Portland Schooner Co., or take a casual cruise onboard the mail boat. According to Naylor, “If you haven’t taken a sunset cruise on Casco Bay Lines, add it to your list. It’s the best midweek reset—affordable, BYO everything, and totally magical. My move? Stop by Rosemont beforehand for a chilled bottle of rosé, a fresh baguette, and some charcuterie, then hop on the ferry and let the sea do the rest.”

Catch a game at Hadlock Field.

If you find yourself in Portland during baseball season, don’t miss the opportunity to catch a Sea Dogs game. Hadlock Field is a quick drive from downtown, and the energy here is unparalleled. Nothing feels quite like summer in Maine than watching a game on a sun-drenched afternoon with a Sea Dogs Biscuit ice cream sandwich in hand.

Head to the beach.

There’s nothing like packing up a cooler full of snacks and spending a couple of hours by the shore. Stop by Mr. Tuna for a bento box, Ramona’s for a hoagie, or Rosemont Market & Bakery to build your own snack platter before heading to Willard Beach in South Portland, Crescent Beach in South Portland, and local’s favorite Ferry Beach in Scarborough. Naylor says, “I’m a big believer in the beach being a year-round activity. My friends and I are at Kettle Cove most Saturday mornings in January, breakfast burritos in hand. The proximity to beaches is part of what makes Portland so special—15 minutes in any direction and you’re there.”

Stop by a brewery.

If there’s one thing Maine does well, it’s craft beer. With more than 100 breweries in the state, you’re nearly guaranteed to find your favorite style around Portland. If you’re a beer enthusiast, it’s worth carving out some time to spend a few hours hopping between some breweries. Oxbow, Allagash Brewing Company, Bissell Brothers, and Bunker Brewing Co. are all local favorites.

Best Restaurants

Crispy Gai

Crispy Gai will make you rethink your entire evening whenever you find yourself in its orbit, suddenly scanning the block for a parking spot to sneak in a quick visit. Between its stellar bar program with original takes on tiki-style classics and crave-worthy wings dusted with spices you’ll be dreaming of for weeks, Crispy Gai is an absolute must-visit.

Magissa

Magissa is a Greek-style taverna in East Bayside that’s owned and operated by the team who was behind The Greeks of Peaks food truck. The menu features small bites, meze, and shareable dishes that are exactly what you’ll need after spending a day hopping from breweries, beaches, or both. The food and cocktails are creative, expertly executed, and made with care.

Eventide

It’s impossible to talk about Portland without mentioning Eventide. Its brown butter lobster roll—made with warm lobster meat and piled high on a pillowy soft bao bun—and flights of oysters from here and away make vying for a parking spot and facing the ever-present waitlist more than worth it.

Scales

If visiting Portland has you conjuring up visions of feasting on fresh fish while gazing out across the docks in Old Port, Scales is the place for you. The restaurant is slightly upscale, without being fussy, and part of a powerhouse group that operates Street & Co., Fore Street, and Standard Baking Co.. Don’t miss the cloverleaf rolls, halibut with brown butter and hazelnuts, and whatever the custard of the day is.

Twelve

Nestled on Thames Street, Twelve is doing something truly special. The front and back of the house are armed with stellar resumes—and it shows. The team at Twelve puts their spin on classic Maine dishes and ingredients, (think: a martini crafted with kombu). Stop by for a cocktail, order dishes a la carte, or go all in on the prix fixe, but whatever you do, don’t miss out on the lobster roll served on a flaky croissant.

Best Time to Visit

If budget isn’t a consideration, you’ll be hard-pressed to find a better time to visit Maine than late June through mid-September. Of course, you won’t be the only one with this idea, so be prepared to pay a premium for lodging and book your reservations well ahead of time. If you’re willing to trade in a far less crowded city for some cooler temperatures, consider planning a visit during late Spring (April-May) or early fall (late September-October). The weather will still be mild, but the uptick in visitors during high season is stark and the city may be much more enjoyable in the shoulder seasons.

How to Get There

If you’re lucky, you can catch a direct flight into Portland International Jetport (PWM), which is just 15 minutes from downtown Portland. Otherwise, fly into Boston’s Logan International Airport and either rent a car to drive the roughly two hours north to Portland, take a bus via Concord Coach, or hop on the Amtrak Downeaster for the approximately 2.5-hour journey. Both operate year-round.

Neighborhoods to Visit

Washington Avenue

While visitors may flock to the Old Port, Washington Avenue is where you’ll find locals on their days and nights off. Be sure to carve out a couple of hours to explore the bars, restaurants, and shops on Washington Avenue. Stop by Maine & Loire for a bottle of wine (or two) to bring back to your hotel, peruse Onggi for some ferment-forward pantry staples, snag some snacks from Sissle & Daughters, and browse through rare and vintage cookbooks at Rabelais.

Eastern Promenade

Since there’s so much great food in Portland, you’re going to need a place to work up an appetite before your next meal. Enter: the Eastern Promenade. The 78-acre park features a two-mile harborside stroll that has sweeping views of Casco Bay and the Portland harbor, plus plenty of benches and green space if you just need a place with great views to relax. Naylor says, “I love strolling down the Eastern Promenade Trail—it drops you right onto Commercial Street, which is perfect for a little shopping, restaurant hopping, or just watching the working waterfront in action.”

South Portland

Just across the bridge from the Old Port is South Portland, home to stellar beaches and some standout food. Don’t miss Night Moves Bread, SoPo Seafood, and Red’s Dairy Freeze—all ideal stops before or after a walk on Willard Beach.

Old Port

Home to the working waterfront and souvenir shops galore, the Old Port is a popular area in the city. While there are tourist traps here, some gems do exist in this part of town, too. Room for Improvement is a cozy dive bar serving up fun takes on classic cocktails and snacks like the Red Snapper, Maine’s illustrious neon-red hot dogs. If your accommodations have a kitchen, be sure to visit Harbor Fish Market, where you’ll find Maine lobsters, clams, mussels, and more. Grab a lobster roll at Luke’s Lobster and get ready—the team will be reopening Portland’s legendary Dry Dock restaurant later this summer with chef Matt Ginn at the helm.

How to Get Around

Portland is a walkable city, but if you want to venture outside of downtown to visit nearby beaches, you’ll want to have a car. Ride-share services are fairly available and affordable, but wait times can be longer during off-peak travel times. You can take the Amtrak Downeaster to nearby towns up the coast as well. There are rental car companies based at Portland International Jetport, but be sure to book in advance if you’re visiting during the summer or other busy times throughout the year, as rentals can hit capacity quickly.