Portland is the largest city in Maine, and its historic Old Port has never looked better. Here’s a list of some of our favorite things to do in Portland, Maine, plus our picks for where to eat, shop, and stay in the area. Read on, then let us know your favorites!

Sunset at Portland Head Light

Stephen A. Clarke

Best of Portland, Maine
Yankee Editors’ Choice Awards

Best Things to Do in Portland, Maine

Best Paddling Adventure | Maine Island Kayak Tours

If you’re itching to go beyond simple float-toy kayaks to maneuver a true sea kayak in gentle surf and find soft landing spots on rocky shores, these half- and full-day tours should be right up your alley. Athletic beginners are also welcome to join the explorations of the Casco Bay archipelago, which begin at Kayak Beach next to the island ferry dock. Two-hour sunset tours reveal a glowing city skyline hard to see from any other vantage.

Best Bookstore | Print

True indie bookstores have become nearly as rare as phone booths, but a few brave souls keep opening these shrines to the literary life. Along with best-sellers and general fiction, Print champions Maine authors, poetry, small presses, and young adult literature. It also hosts myriad readings, signings, and book discussions. Richard Russo novels account for about three feet of the Maine shelves—natural enough, given that daughter Emily is a co-owner here.

Best Brewery Experience | Allagash Brewing Company’s Grand Cru Tour

Beer geeks lust after the kind of experience offered on the Grand Cru Tour, but only a dozen are allowed on each three-hour sojourn. Go behind the scenes to see brewing, aging, and bottling. Each tour differs but count on barrel tastings, samples of rare beers, and a visit to the “coolship,” where wild yeasts kick off the lambics. A member of the tech staff pops in on every tour. You’ll glean inside trade information—but not the name of the secret spice in Allagash White. All proceeds go to local charities. Reservations essential.

Best Bay Tour | Lucky Catch Lobster Tour

Cruise Casco Bay aboard the Lucky Catch, and in addition to learning all about lobsters, participants can help haul, bait, and set traps and perhaps even catch dinner.

Best Historic House Museum | Victoria Mansion

Widely considered the most magnificently ornamented dwelling of its period remaining in the country, the mid-19th-century Victoria Mansion retains about 90 percent of designer Gustave Herter’s original furnishings. Jaw-droppers include a 6-by-25-foot stained-glass ceiling window, mind-boggling trompe l’oeil wall and ceiling flourishes, and the dizzying colors and patterns of the Turkish Smoking Room.

Best Historic Lighthouse | Portland Head Light (Cape Elizabeth)

In Fort Williams Park, just 4 miles from downtown Portland, Maine’s oldest lighthouse, commissioned by George Washington, guards the harbor. Visit the museum in the keeper’s house and picnic in the park.

Best Bay Tour | Lucky Catch Lobster Tour

Aimee Seavey

Best Places to Eat in Portland, Maine

Best Bakery (Sweets) | Two Fat Cats Bakery

The iconic pies of the Pine Tree State couldn’t be more different. Maine blueberry pie celebrates the tart juiciness of wild blueberries as it bubbles through the slits of a flaky crust. At the other end of the wholesomeness spectrum, the whoopie pie cements together two slightly rounded cocoa sponges with a sugary “creme” that soothes your inner child by satisfying even the most extreme sweet tooth. Two Fat Cats does them both to perfection.

Best Deli | Rose Foods

The Back Cove location doesn’t deter those with a jones for authentic New York deli fare. Rose does a booming lunch business with corned beef or egg salad on house-baked caraway-seeded rye, while couples often gravitate to the “Fishermen’s Feast for 2,” which gathers all the house-cured fishes (including lox cured with pastrami spices) onto a single platter with pickles, onions, capers, cream cheese, and fresh golden bagels. In a nod to bubbes everywhere, one dining room wall is papered with a recherché rose pattern.

Best Fried Clams | Bob’s Clam Hut

A roadside staple in Kittery since 1956, Bob’s built its fame on two styles of fried clams: “Bob’s,” which are dipped in a mix of unseasoned flours and fried to light crispness, and “Lillian’s,” which make two passes through the flours with an egg wash in between, creating a crunchier clam. The double-barreled magic has transplanted perfectly to Portland’s East End. The glass-walled modernist box that houses the restaurant is an urban analog to the funky roadside original, complete with picnic tables.

Best Italian Cuisine | Piccolo

Step out of Portland and into the Italian countryside at Piccolo, a pocket eatery on the edge of the Old Port, where chef Damian Sansonetti draws on the food of his childhood. The small, ever-changing menu emphasizes the rustic cuisine of the Calabria and Abruzzi regions with entrées—such as the signature house-made cavatelli pasta with lamb’s-neck ragu—created from a conscientious mix of ingredients sourced from Italy and Maine.

Best Sushi | Miyake

James Beard Award–nominated chef Masa Miyake takes Japanese cuisine to a new level, using ultrafresh ingredients (some sourced from his own farm) and employing Japanese, Italian, and French techniques. While you can’t go wrong ordering from the à la carte options, you should splurge at least once on the omakase, or chef’s tasting menu, for a dining adventure.

Best Oyster Bar | Eventide

The bar’s huge block of granite and ice topped with oysters signals you’ve come to the right place. Eventide made the old-fashioned oyster bar cool again by offering at least a dozen varieties—mostly from Maine but a few from “away”—on the half shell along with a sassy cocktail program. (The Dirty Dirty Martini pairs the booze with olive brine, oyster brine, and hot sauce.) The fried fish is often hake, an underutilized species this side of the Atlantic but a Parisian favorite.

Best Doughnuts | The Holy Donut

It has long been a tradition in Maine potato country to add mashed spuds to doughnut batter, yielding a fluffier, moister dunker. So when Leigh Kellis decided to open a doughnut shop in Portland in 2012, it was only natural that she would make her rounds with potatoes. The results not only nail the perfect texture but also come in 20-odd flavors that are uniformly excellent. Don’t miss the chocolate glazed sprinkled with sea salt, the ideal foil to all that sweet, chocolatey goodness.

KEEP READING: More Favorite Restaurants in Portland, Maine

Best Downtown Hotel | The Press Hotel

Best Places to Stay in Portland, Maine

Best Eco-Friendly Lodging | The Chadwick

Here’s proof that a light environmental footprint can go hand in hand with creature comforts. When you’re luxuriating on the comfortable mattresses or feasting at breakfast on the signature lobster eggs Benedict, you’d never give a thought to the Chadwick’s staunchly green philosophy. The B&B composts all organic materials, uses low-energy LEDs, avoids printed communications, and is equipped with low-flow toilets, showerheads, and sinks. The Gilchrist & Soames body products even help support honeybee research—proof that doing good can also feel good.

Best New Hotel | The Francis

Originally a private home, this 1881 West End mansion stood abandoned for a decade before the current owners rescued and restored the property to create one of Portland’s most appealing lodgings. Vintage stained glass, a tiled fireplace in the parlor, and floors with striking inlaid patterns provide the historic framework for contemporary decor in muted grays and tans. A second-story spa enhances that low-key serenity with a choice of massages and full-body scrubs.

Best Downtown Hotel | The Press Hotel

The full-service Press Hotel’s décor takes its cue from its home in the former headquarters of the state’s largest newspaper. Fronting on Congress at the head of Exchange and Market streets, the location is ideal for exploring the city. The hotel’s Union restaurant earns raves.

Best Romantic Getaway | The Inn at Diamond Cove

You and your significant other can leave both car and cares on the mainland when you hop a Casco Bay Ferry to Great Diamond Island, where bicycles and electric golf carts are the chief alternatives to walking. An inspired redeployment of the former barracks of the 1890s Fort McKinley, the 44-room Inn at Diamond Cove offers a plush and tranquil retreat. To up the intimacy factor, ask for a parlor suite with fireplace for snuggling on a cool night, and reserve a waterfront table at the inn’s sister restaurant, Diamond’s Edge.

Best City B&B | Inn at Park Spring

The tastefully updated Inn at Park Spring occupies an 1835 brick townhouse in Portland’s upscale West End neighborhood, putting guests within easy walking distance of the sights, shops, and restaurants of downtown and the arts district. The guest rooms and public spaces are decorated with restraint (nothing froufrou here), and attentive innkeepers pamper guests with hearty breakfasts and afternoon treats.