That being said, with so much to do and see (and eat!), it can be difficult to decide where to spend your time, especially if you're in town for a short weekend getaway. For an effortlessly authentic vacation, experience Portland as a local. Here's your perfect one-day itinerary.
Morning coffee
Tandem Coffee, located in a repurposed gas station, is a city favorite
Coffee is interwoven with New England's history; it was in coffee houses that patrons first heard whispers of a coming revolt against our then tea-drinking rulers. Since then, coffee in New England has become synonymous with Dunkin Donuts. But in the past decade, the tides have turned away from chains, and a wave of independent cafes has hit New England once again. In Portland, there is an abundance of charming cafés, but Bard Coffee, Tandem Café and Roastery, and Speckled Ax, which roasts its beans in a wood-burning oven, are notable favorites. Enjoy your coffee with a pastry, or take it to go and grab breakfast at local foodie mecca Central Provisions, where your basic bread and butter comes with Riesling sabayon and trout roe.
Sweeping views in Cape Elizabeth
Head south down the coast to Cape Elizabeth, on a gorgeous stretch of stately waterside homes and preserved land. Two Lights State Park is an excellent place for a walk, with trails running along the rocky headline and sweeping views of Casco Bay and the Atlantic Ocean. Be sure to check out the two lighthouses that give this park its name—the first coastal lighthouses in Maine, built in 1828—and the subject of Edward Hopper's famous painting "Lighthouse at Two Lights." Enjoy a lobster roll at the Lobster Shack for lunch, where you can sit outside at the base of the lighthouse, or take a short drive to Bite Into Main Commissary in Scarborough, which is dishing up some delicious and original twists on the Maine original.
Drink it off
The Fermentory makes its own kombucha tea in unusual flavors
Catch an early afternoon drink in Riverton, where several fledgling breweries are getting their start at One Industrial Way, a repurposed industrial building just past the well-known—and well-traveled—Allagash Brewery. Here, in what's known as Portland's "neighborhood of beers," you'll find some innovative craft breweries, each serving their take on classics like the New England double IPA. Sample multiple brews with a flight, or go for full glasses of your favorites. You'll also find outdoor picnic tables, music, and a palpable sense of comradery.
Not a drinker? Try a glass of tangy kombucha at Urban Farm Fermentory, which has a tasting room with its seasonal fermented teas on tap (as well as alcoholic options like mead and cider) in flavors like Elderberry, Ghost Chili Pepper, and Toasted Oak.
Downtown shop and stroll
Score vintage architectural goods at Portland Architectural Salvage in Old Port
Head to Portland's Old Port district and stroll the cobblestoned streets as you browse a bevy of locally-owned and operated shops. Portland Dry Goods and David Woods Clothiers Haberdashery & Tailor Shop, offer the best taste of Portland's rugged chic aesthetic and appreciation for artisan goods. On the less expensive side, there are a number of fantastic vintage stores with unique finds, including Portland Flea-for-all for clothing and jewelry and Portland Architectural Salvage for furniture and hardware. Chellis Wilson, described as a "retail experience" rather than a store, displays locally made goods ranging from furniture to bicycles and is worth a drop-in (yes, you can still buy, but in Portland, that isn't the point.)
A foodie's night out
The Honey Paw has earned foodie fame
For a small city, Portland has received some serious recognition for its restaurants, which have been reviewed in national newspapers like The New York Times. You should weather the long lines to get into Duckfat, Portland's most beloved casual eatery serving up some of the city's finest food, most of it fried in—you guessed it—duck fat. The Belgian fries served alongside a palette of fancy mayos, Poutine topped with velvety duck gravy, and "the original" duckfat milkshake (thankfully no real duck fat in here, just Tahitian vanilla and creamy homemade gelato) are rich, indulgent, and the farthest from a kale salad you could possibly get. Also worth trying are The Honey Paw, which serves up a variety of delectable Asian noodle and rice dishes from Vietnamese Pho to Chinese congee, and Fore Street, an upscale farm-to-table joint with a seasonally rotating menu.
Bar hop
At Vena's Fizz House enjoy original cocktails and homemade bitters
End the day with a tour of Portland's thriving bar scene. Vena's Fizz House, which serves homemade juices and sodas by day, has the best, if not the most original, cocktails in town (including beer cocktails which, miraculously, work well), most of which include one of the shop's homemade bitters. For a taste of Portland's underground scene, try Novare Res Bier Café, a beer garden with outdoor seating and an ever-changing roster of tasty local and international beers that's as difficult to find as it is to leave.
Where to stay
The Press Hotel, located in Old Port in a former newspaper building, is a fun and artsy boutique hotel with an excellent restaurant and rooftop views. Newspaper paraphernalia throughout offers endless charm. $200-250 a night.
For a quieter getaway, try the Danforth Inn, an elegant bed and breakfast in an 1820s Federal-style mansion just 10 minutes away from downtown bars and restaurants. A funky modern interior will surprise and delight. $150-200 a night.
With Memorial Day coming up, you might want to consider making Portland your destination. Not only is it convenient to get to and easy to get a taste of the city in just a few short days, but the city also has everything you need to welcome summer: beachside dining, ocean views, and the best lobster on the East Coast.