Nationally acclaimed dining destination Portland, Maine, is about two hours from Boston, whether you take Amtrak’s Downeaster from North Station, the Concord Coach bus from South Station, or drive, making it the ideal getaway for a food-packed weekend. If you only have a weekend to spend in Portland, the following itinerary serves to complement our list of essential restaurants, providing a choose-your-own-adventure insider’s guide to painting the town lobster red.

11 a.m.: Begin with brunch

Portland’s brunch game has never been stronger, making it the perfect meal to start a weekend of ambitious eating. At Ocotillo, the West End sibling to the East End’s popular barbecue spot, Terlingua, find solace on the quiet back patio or grab a comfy circular booth upholstered with rust red velvet. Ocotillo channels Tex-Mex into brunch standouts like a smoked brisket hash with poached eggs and house hollandaise and buttermilk-masa pancakes decked with caramelized pineapple syrup, hibiscus sugar, and maple sea salt butter served alongside refreshing morning beverages like the bright green, herbaceous Verdita-rita. As you move on, grab something for the road from James Beard Award-winning Zu Bakery next door.

Alternative: Start your day at Dutch’s, whose cafeteria-like space belies the quality of crispy hash browns and housemade baked goods that elevate hits like chicken thigh biscuits smothered in sausage gravy and bluebarb pie doughnuts.

Once you’re temporarily sated, it’s time for some culture. Head to the Maine Historical Society and the Wadsworth-Longfellow House for thoughtful exhibitions like Stitches, an exploration of 19th-century Maine quilting traditions; the Victoria Mansion for a tour of an elaborate pre-civil war home; or the Portland Museum of Art for the state’s oldest and largest public art collection, including works by American landscape artist and former Maine resident Winslow Homer.

Along the walk, shop for art and vintage finds at dozens of local storefronts like Weekend Vintage, the Merchant Company, and Soleil, a gift shop that houses a vending machine for collectible $1 mini food prints by Portland’s Anastasia Inciardi.

4 p.m.: Take a lobster break

If you come to Maine, you’ve got to eat lobster. Dive into a new favorite like Highroller Lobster Co.’s Lobby Pop TM — a cornbread-battered lobster tail on a stick — or chef Mimi Weissenborn’s rich yet airy lobster popover at Sur Lie. If you’re in the mood for a more traditional lobster roll experience on the working waterfront, head to Luke’s Lobster for rolls with a captivating view, or have a seat at low-key institution Becky’s Diner for a fresh-shucked quarter-pounder — there’s nothin’ finah, as the local saying goes.

6 p.m.: Get a pre-dinner drink

At Jewel Box, bartender and owner Nathanial “Nan’l” Meiklejohn creates an atmosphere of comfort and delight that attracts a crowd of artists, queer folks, and bon vivants — people with open minds and good taste. Amid curated grandma-core and a dreamy wall mural, the creative cocktails and playlists always hit. Order a drink like the Lovers, a blend of fenugreek and coconut rums, lime juice, cane sugar syrup, and Bluet, Maine blueberry sparkling wine.

Alternative: Hit up Cuties, a new all-day spot from the cunning minds behind renowned high-low cocktail dive Room for Improvement. Cuties focuses on low-intervention wines by the glass or in some cases as a sidecar, like the pet-nat that accompanies the Pornstar Martinez, a clarified passionfruit number featuring Old Tom gin and vermouths.

Portland’s bakery and brunch darling Bread & Friends is now a winner for dinner as well. Expect a tight menu with seasonal dishes like grilled radicchio with black vinegar XO sauce and Bayley Hazen blue cheese on housemade marble rye crostini, consommé with collard greens and mascarpone tortellini decked in country ham and peas, and dry-aged duck with plum chutney. End the meal with a dreamy orange creamsicle soda made in-house, or a glass of A7 Americano, an aromatized wild Maine blueberry wine infused with herbs and fortified with brandy, from R.A.S.

Alternative: Opt for an evening of pizza and natural wine at cool, casual Friends & Family. Start the night with a jamón tower for the table, of course.

9 p.m.: Post-dinner games

After dinner, it’s free to enter Arcadia National Bar’s Skee-Ball tournament, or you can pump quarters into retro pinball and arcade cabinets while enjoying late-night bites like mushroom-topped pizza and beers from Oxbow and Sacred Profane. The cocktails here, crafted by co-owner Nicole Costas-Rosa, are some of the city’s sleeper hits — try the mezcal- and watermelon-forward Pink Pony Club.

Alternative: Have a nightcap at the Scandinavian-style cocktail bar that helped launch Portland’s cocktail scene in the mid-2010s: Portland Hunt + Alpine Club. The spicy, smoky Bone Crusher is a perennial favorite.

9:30 a.m.: Grab a bite before the farmers market

All-day cafe Smalls is a charming spot to eat white bean toast with a jammy egg, shop for adorable home goods and sundries, and devour a slice of gorgeous, seasonally inspired cake from Siblings first thing in the morning before heading over to Deering Oaks Park for Saturday’s Portland Farmers Market. There, you’ll find treasures like earthy Haymaker English-style cheddar from Balfour Farm, jars of well-aged fermented onions from Gracie’s Garden, and wild blueberries from Lost & Found Farm.

11:30 a.m.: Get out on Casco Bay

One of the easiest, most cost-effective ways to get off the Portland peninsula and out on the water is with the Mailboat ferry, a scenic ride to the islands of Casco Bay. Get off at Peaks Island for BYOB wood-fired Neapolitan-style pizza served al fresco at Il Leone, or head to Great Diamond Island’s Crown Jewel, a bright and airy bistro that nods to the tropics with dishes like corn agnolotti featuring Maine crab and seared whitefish with salsa verde.

Alternative: Board the 74-foot-tall ship Frances, a historic replica built and captained by Megan Jones, for a Wine Wise Wine Sail with curated tastings led by gregarious sommelier Erica Archer.

3 p.m.: Shop the waterfront and have a little treat

Portland’s bustling Commercial Street is full of enticing shops for food lovers, like LeRoux Kitchen and Browne Trading Co. Treat yourself to a wicked-fresh raw seafood snack like scallops from revered fishmonger Harbor Fish Market or sea urchin from uni processor ISF Trading’s warehouse, followed by a sweet pastry at Standard Baking Co. or a frozen treat from Gorgeous Gelato or Mount Desert Island Ice Cream.

5 p.m.: Break for happy hour

At Papi on Exchange Street, the cocktail and food menus sing with Puerto Rican flavors. For a late afternoon pick-me-up, try the Carajillo — Licor 43 and Italian espresso shaken over ice — and don’t miss food specials like the jibarito, a panko-crusted chicken cutlet dressed and sandwiched between fried green plantains.

Alternative: Head to the intimate, 20-seat Argentine Bodegón-influenced Franciska Wine Bar, whose menu highlights small-grower South American producers.

On Congress Street, check out Benny’s, the buzzy new restaurant from Josh Sobel of Philadelphia-style sandwich shop Ramona’s. Here, Sobel again wins hearts and stomachs with his homage to Philly’s Italian American heritage, from the portraits of celebrities like Sylvester Stallone on the wall above the long banquet to menu classics like eggplant parm, cheesesteak, and linguini and clams with long hot peppers alongside cocktails like the Balboa, featuring bourbon, amaretto, and citrus topped with a pink Lambrusco-Scotch foam.

Alternative: Go for well-seasoned garlic greens and dry-aged pork katsu sandos stuffed with fried Brussels sprouts and slathered in charred scallion mayo at family-owned izakaya Mami.

Stop into Speckled Ax Wood Coffee Roasters for an Early Riser medium roast. Try it with a Grand Trunk breakfast sandwich stacked with housemade hash browns, green tomato chutney, kewpie mayo, Gruyère cheese, and an egg on a Portuguese muffin made by chef Carlos Duarte, previously of Prentice Hospitality.

Alternative: Grab an olive oil brioche sticky bun swirled with brown butter and cinnamon and glazed with orange cream alongside an iced malt cold brew at Tandem Coffee.

11 a.m.: Check out the East End

The East End used to be a quiet area populated largely by under-the-radar neighborhood spots like pupusería Tu Casa and old-school Italian goods purveyor Micucci Grocery Co. That changed in the 2010s with the arrival of food and beverage perfectionists like Rising Tide and other craft breweries in East Bayside, Maine & Loire, a pioneering natural wine shop on Washington Avenue, and the Portland Food Co-op on Congress Street for largely local groceries and snacks.

Now, you could spend all day bopping from one banger to another without breaking a sweat: Onggi Ferments for all things aged and preserved; Root Wild for unbeatable kombucha; Rabelais for antique food books; Oxbow for funky beer and fries via Duckfat Frites Shack; Anoche for hard cider; Sissle and Daughters for cheese, wine, and everything else you’d serve for girl dinner; and the list goes on.

1:30 p.m.: Slip over to South Portland

Formerly an underwhelming collection of strip malls, Knightville has finally glowed up into one of Portland’s buzziest neighborhoods. (Okay, it’s technically in South Portland across the Casco Bay Bridge, but regardless, it’s a Portland-area hot spot.) Stop here on your way back south for Japanese-style bar fare and beers from a Maine Brewing Co. alum at the Send Brewing Co., impeccable breads from Night Moves, a glass of Maine’s own Oyster River Winegrowers Morphos pet-nat with views of Portland proper from across the water at Lambs, and some of the country’s best seafood at SoPo Seafood market and raw bar.

Get a good night’s sleep at the 48-room Longfellow Hotel, Portland’s first independently owned full-service hotel in decades. Longfellow highlights neighborhood contributors such as Ugly Duckling for pastries, and Siobhán and Mike Sindoni of Wayside Tavern run the bar program.

Alternatively, check into the 135-room, six-story Canopy by Hilton Portland Waterfront, home to Luna, the city’s only indoor/outdoor rooftop bar and restaurant overlooking Casco Bay. Make sure to enjoy the view while sipping a slushy cocktail featuring housemade granita and Prosecco.
If you want to spend extra time on the islands, stay at the Inn at Diamond Cove. This charming, family-friendly escape offers 42 rooms and suites in the former Fort McKinley military complex for easy access to the tranquil, car-light island with a semi-secret beach rich with seaglass.