The Perfect 3-Day Weekend in Portland, Maine: Island Hopping, Lobster Rolls, and Mighty Fine Microbrew

Sure, there are plenty of lobsters and lighthouses in Maine. But lots of tourist-baiting coastal communities can serve up that classic New England combo of fried seafood joints and briny fridge magnets, while ultimately offering little more than a beach to keep out-of-towners occupied. That’s not what makes Portland a long weekend no-brainer. Rather, it’s the spirited and delicious efficiency of this classic American town that remains its greatest evolving asset—putting the sum of all of its parts within easy reach. At about three miles wide and traversable by foot, there’s no shortage of things to do in Portland over three perfect days.

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The heart of Portland is a peninsula bookended by greenspaces with a civilized “jetport” a speedy 15-minute Uber ride away from all the action across the Fore River. In larger cities, three days is hardly enough time to sort out cardinal directions, find a decent cup of coffee, and a tchotchke shop. Here in Portland, that kind of walkability ensures you leave feeling like you’ve gotten a real sense of the place, while collecting enough “next times” to plan a return. In Portland alone, you’ll soon grasp why “The Way Life Should Be” is its parent state’s official slogan.

While you’re here, there’s a bona fide city vibe with an embrace of the natural world that urban parks can’t match. There are outdoor spaces that range from craggy coastlines dotted with secluded beaches to exhilarating hiking and ferries ready to shuttle you to far-off islands for the day. Then there’s the culinary scene that rivals any major city—even if seafood isn’t your thing. Some of New England's finest Victorian-era architecture is all around you here. On days when gray weather rolls in off Casco Bay, some of the finest museums, art galleries, and craft brew scenes in New England will fill in the gap.

While the locals are welcoming, visitors will remain as such for a while. As the saying goes, you’re not a real Mainer until generations of your family have lived here. All good. Here’s how to crush your next Portland getaway and squeeze the best of the city into a long weekend.

How to Get to and Around Portland, Maine

Portland International Jetport (PWM) connects the city to major hubs like New York, Atlanta, Philadelphia, Washington D.C., and as far west as Chicago. The city also sits just off I-95, which is the main route for drivers headed there from the East Coast. You likely won’t need a car in Portland as ride-share services cover the town, even in winter. During summer months, flights to the area tend to be cheaper headed into Boston’s Logan Airport (BOS), which is about a two-hour ride away.

A clean, reliable, and inexpensive bus service, Concord Coachlines, connects Portland to Boston (and a few other cities like New York) with WiFi, dropping you just across the Fore River from the airport. From there, it’s about a 15-minute ride to downtown Portland. Situated mostly on a three-mile-long peninsula, Portland has about 21 neighborhoods, many of which are split into seven major areas from the preserved Victorian architecture of the West End to the working waterfront of Old Port. Most of what you want to visit is within about an hour’s walk.

When to Visit Portland, Maine

Like any coastal town, summer is peak season here (and priced accordingly), with warm, sunny days and crowds eager to take it all in from June to the end of August. Fall brings dry, cooler air, and plenty of L.L.Bean fleeces, which makes for comfortable walking, less crowding, and ideal fall foliage appreciation in surrounding areas lit up with autumn colors. If you can handle the colder temps, you’ll have the run of the place in winter, when ice skating, cross-country skiing, and snowshoeing take over. Starting in December, the average high is in the upper 30s, creeping into the 50s with the arrival of crowd-free spring.

Where to Stay in Portland, Maine: Best Boutique Hotels

Blind Tiger

The growing Lark Hotels, which has a number of tasteful, boutique properties, most of which are grouped in the northeast, has two Blind Tiger outposts in Portland. An easy walk to the Old Port area of Portland, the 1823 Federal-style mansion on Danforth Street is an inn with nine private guest houses weaved into three floors, mixed in with public gathering spaces. During Prohibition the building hosted gatherings in the basement, which is now a billiard room. But today, each room has a different vibe, like the moody Diavolo room with dark walls and a wood-burning fireplace, and the grander Bon Viveur with a four-poster bed, living room, armchairs, and private deck on the second floor. This year Lark opened a second Blind Tiger a half-mile west on Carleton Street, a few blocks away from the Western Promenade. Originally an inn, the 1869 Second Empire building has six rooms spread over two floors in a home squirreled away on a residential street, with two public living rooms, each with a fireplace.

The Francis

Like the Blind Tiger, The Francis reimagines a private home into 15 private rooms, this time within the bones of a building that’s slightly younger: 1881. The brick Victorian, which had a stint as a funeral home before the renovation turned it into a boutique hotel, bears the name of its original designer, Francis Fassett, who had a hand in several pivotal Portland buildings—including the former city hall. Now on the National Park Service’s Registry of Historic Places, the rooms (four on the first floor are pet friendly) have more modern styling and location in the West End, across the street from the excellent Tandem Coffee and Bakery, itself housed in a 1930s gas station. From here, you’re a quick, 10-minute walk to the Portland Museum of Art, and an even shorter one to the Wayside Tavern next door.

Where to Eat: Best Breakfast, Lunch, and Dinner in Portland, Maine

Becky’s Diner

Set back a few feet from the Fore River, you’d need to be on a boat to be any closer to the docks than a window seat at Becky’s. “Try the homemade corned beef hash at this classic breakfast joint,” says Portland local Seth Levy. “It’s loud, well-lit, and cheery with completely average coffee and reliable diner classic dishes.” Arrive just after it opens at 5 a.m. and you might catch some lobstermen heading out for a day on the water.

Slab Sicilian Street Food

Part pizza joint and part beer hall, Slab hits heavy with Sicilian-style pies that clock in at 1 pound per slice. But the real story here might be the hefty sandwiches, like the prosciutto and fig, or the mortadella special. Taps feature a range of local breweries like Allagash and Rising Tide, and even some ciders brewed in New England. With a wall of windows, the interior is bright and perky with a beer garden-like patio.

Fore Street

With a view of the open kitchen and its beating heart of a roaring fire, Fore Street is an upscale dinner leaning heavily on local seafood and fatty, smoky dishes, like steaks, foie gras, and its famous wood-smoked lobster. Some dishes are cooked over a turnspit, which today might feel showy, but Fore has been doing the local food thing longer than just about anyone in Portland. The dining room’s brick, reclaimed wood, and soapstone feel very Maine-inspired, just like the food.

Related: A First-Timer's Travel Guide to Acadia National Park

Where to Drink: Best Bars in Portland, Maine

Novare Res Bier Cafe

In a town known for beer, Novare Res stands apart for its formidable selection of rare craft beers with more than 33 taps and 170 bottles. This 2020 James Beard semifinalist is housed in a bank vault filled with chalices given to dedicated patrons who drink through their entire list. The New England Double IPA, a style pioneered here, has a hazy, unfiltered appearance and massive hop aroma that will set the tone for the night.

Portland Hunt + Alpine

With a ski lodge vibe, this cocktail bar offers a reprieve from the beer (though you can order that too) with a creative lineup of drinks—like the orchard sour, which Portland Hunt + Alpine describes as “putting on your flannel and picking some fruit.” Don’t sleep on the snacks though, with homemade pretzels, oysters, and brown butter-topped popcorn.

​​Don't-Miss: Top Attraction in Portland, Maine

East End Beach

Sitting on the tip of the Portland peninsula is East End Beach, the city’s only public stretch of sand and rocks—and the quintessential slice of urban Maine shoreline. Strolling here with your morning coffee while taking in panoramic views of Casco Bay is that simple-yet-profound moment you’ll recall next week back at the office. You’ll see sailboats coming and going, maybe some seals off in the distance, and the beach itself is usually beautifully empty save for a few dog walkers.

Savvy Tip for Visitors to Portland, Maine

Maybe you’ve heard natives can sniff out someone who is “from away” pretty easily. “Mainers have a long and noble tradition of recognizing tourists,” says Seth Levy. If you want to try and fit in: “The unofficial uniform of a flannel shirt, L.L.Bean fleece, and battered jeans is a sure thing.”

Day 1: Exploring the Old Port

The Old Port area is the most iconic neighborhood in Portland, but you’ll need a plan to avoid the touristy spots. Head south out of The Blind Tiger towards the sound of seagulls until you reach Smalls, a compact, all-day café that has interesting breakfasts along with handmade candy for later.

Grab a coffee to go and head east to the heart of the Old Port to check out the architecture of buildings like Mariner’s Church, which dates back to 1828, and was designed by the same architect who worked on Boston’s Quincy Market. Tucked in around all the shops you’ll find other significant architectural buildings like the U.S. Courthouse, Custom House, and the Portland Regency Hotel, which opened in 1895 as the armory for Maine’s National Guard. Stroll along Middle Street for one of the best-preserved Victorian blocks in Maine.

Related: 4-Day Weekend Travel Guide to Kennebunkport, Maine

Pick up a late-morning snack by heading south towards The Holy Donut—a local donut shrine featuring the most nourishing donut you’re likely to find anywhere, made with riced potatoes. Then spend the rest of the afternoon walking up and down the piers and wharves off Commercial Street and taking in the views off the ends of Maine State Pier, Custom House Wharf, and Portland Fish Pier. Break up the tour by stopping at Becky’s Diner or another local favorite, Gilbert's Chowder House.

It’s time to head back to the Blind Tiger and freshen up before dinner, so call an Uber if you don’t have the energy to hoof it back the 20 minutes (a belly full of chowder will do that to you). But if you’ve still got some steps to crush, duck into the Portland Museum of Art, which is open until 6 p.m. most days. The highlights here include works from Monet, Thomas Moran, Jackson Pollock, Vincent Van Gogh, and Andy Warhol.

Reward yourself for all those steps with pasta for dinner at Leeward, where things kick off with house-made focaccia. If you missed out on lobster today, go for the bucatini with fra diavolo that combines tender crustacean meat with furious Calabrian chilis.

Day 2: Island Hopping

After morning coffee, head out to pick up provisions for a picnic lunch at Sisters Gourmet Deli, known for their thick sandwiches and wraps. Walk through Munjoy Hill to the Eastern Promenade to take in the sights from the edge of the peninsula. Now head toward the direction of the Old Port to board the Casco Bay Lines. These boats are more than just nostalgia, as they carry people, supplies, and mail to the half-dozen islands off the coast of Portland.

Pick one or two islands to explore, sometimes by golf cart, or do the whole three-hour tour by stowing away on Casco’s mail boat—first departure is 10 a.m. You’ll get photo-worthy views and understand what it takes to navigate the waters here.

Later that afternoon, head to Brickyard Hollow Brewing, just north of the water’s edge, and peruse your morning’s pics over a cold pint or two. Then head north to Duckfat to do anything but count calories over hand-cut, namesake-cooked fries. Here you’ll find fine reubens, cubanos, and meatloaf, too. It’s a popular spot, so get there early, and expect a line at any time. Walk it off on the 1 ½ mile route back to your hotel, catching a glimpse of the sun setting over the west side.

Day 3: Pub Crawling

You could research the dizzying number of breweries in and around Portland for a custom walking tour of your own. Or you can just plunk down $95 and grab a seat with Brews Cruise on the Maine Brew Bus, which handles all the driving while introducing you to some of the best beermakers in town—and, more importantly, their beers. Bus and walking tours generally depart from Portland Beer Hub between 10 a.m and 5 p.m. and last about three hours. Light snacks are also offered along the way.

Once you get back, it's last licks time for shellfish, so head on over to Portland Lobster Company, which took “Best Lobster Roll” honors in a 2022 Best of Portland poll and is lauded for their waterfront dining and views. A few doors down, at the end of the pier, is Luke's Lobster Portland Pier—which got the latest top lobster roll nod for 2023. Either way, here's where to savor the Old Port while capping three days of pure Portland perfection.