For a small coastal city, Portland, Maine (more info) has an impressive number of things to do that can easily fill a long weekend. Along with sweeping views of Casco Bay (more info), award-winning bakeries, dockside seafood, craft breweries, and stylish cocktail bars await. This four-day itinerary lets you enjoy some of the city’s most lauded and creative meals while learning about the state’s culinary culture and unwinding by the water.
Itinerary / 4 Days
In Portland, evenings can swing from laid-back beer gardens to elegant bistro dinners by the water.
Photo by Matt McNulty/Unsplash
Day 1Drinking and Dining After Dark in Portland
Fly into the Portland International Jetport (more info)—and arrive hungry. Drop your bags at the airy suites of the Francis Hotel on Congress Street, then walk through the city’s historic Old Port.
Make your final destination Duckfat (more info), a cozy Portland staple known for its Belgian-style duck fat frites and poutine. The small bistro doesn’t take reservations, so if you can’t get a table or would rather enjoy a beer hall vibe, head around the corner to the Duckfat Frites Shack at Oxbow Brewing Company (more info) on Washington Street.
For before- or after-dinner drinks and snacks, the East Bayside (more info) area teems with chic lounges. One of those is Anoche (more info), a moody Spanish-style cider bar. Another is Après, a ski-themed spot that makes its own hard seltzers and features stylish velvet booths and patio firepits. Nearby on Market Street, you can also grab a seat, a cocktail, and some Scandinavian small bites at Hunt & Alpine Club.
Make your final destination Duckfat (more info), a cozy Portland staple known for its Belgian-style duck fat frites and poutine. The small bistro doesn’t take reservations, so if you can’t get a table or would rather enjoy a beer hall vibe, head around the corner to the Duckfat Frites Shack at Oxbow Brewing Company (more info) on Washington Street.
For before- or after-dinner drinks and snacks, the East Bayside (more info) area teems with chic lounges. One of those is Anoche (more info), a moody Spanish-style cider bar. Another is Après, a ski-themed spot that makes its own hard seltzers and features stylish velvet booths and patio firepits. Nearby on Market Street, you can also grab a seat, a cocktail, and some Scandinavian small bites at Hunt & Alpine Club.
Allagash Brewing’s tasting room
Courtesy of Allagash Brewing
Day 2Educational Tastings and Exceptional Coastal Cuisine
Start the day with breakfast pastries at Norimoto Bakery (more info), a Japanese spot using local Maine ingredients. Atsuko Fujimoto, who won the James Beard Foundation’s outstanding pastry chef award in 2024, whips up miso honey butter cinnamon rolls, blueberry sausage brioche, and onigiri rice balls.
Spend the early half of the day at a local brewery to learn all about Maine’s grains. Head to the Riverton neighborhood and tour the tasting rooms of either Allagash Brewing (more info) or Geary Brewing Company (more info), the first craft brewery in New England following the end of Prohibition. For a grain education not as heavy on the ABV, seek out events hosted by the Maine Grain Alliance; a recent workshop dedicated to corn highlighted the melding of cultures and history in North America.
Then, take a lap around the Back Cove or the Eastern Promenade (more info) and admire the coastal views before freshening up at your hotel. Make reservations at the dockside restaurant Scales (more info) for seared scallops with bacon and oyster mushrooms and the salt cod croquettes. You could also check out the Italian menu at the stylish Via Vecchia (more info). Or, if it’s shaping up to be a warm evening, book a private sunset dinner cruise on a restored 1969 wooden lobster boat for up to six people through Casco Bay Custom Charters.
Spend the early half of the day at a local brewery to learn all about Maine’s grains. Head to the Riverton neighborhood and tour the tasting rooms of either Allagash Brewing (more info) or Geary Brewing Company (more info), the first craft brewery in New England following the end of Prohibition. For a grain education not as heavy on the ABV, seek out events hosted by the Maine Grain Alliance; a recent workshop dedicated to corn highlighted the melding of cultures and history in North America.
Then, take a lap around the Back Cove or the Eastern Promenade (more info) and admire the coastal views before freshening up at your hotel. Make reservations at the dockside restaurant Scales (more info) for seared scallops with bacon and oyster mushrooms and the salt cod croquettes. You could also check out the Italian menu at the stylish Via Vecchia (more info). Or, if it’s shaping up to be a warm evening, book a private sunset dinner cruise on a restored 1969 wooden lobster boat for up to six people through Casco Bay Custom Charters.
You’ll find local oysters on many menus throughout Maine.
Courtesy of Visit Maine
Day 3Brunch, Bay Views, and Bowls of Phở
Early risers can grab breakfast at one of Portland’s tried-and-true joints, like Becky’s Diner (more info), Marcy’s Diner (more info), or Miss Portland Diner (more info), for classic American breakfast platters.
For an option that opens later, check out Bayside American Café’s (more info) brunch, near the Longfellow Hotel (more info), with avocado toast, lobster scrambles, and a mouthwatering cinnamon bun pancake. Or head to the Munjoy Hill neighborhood for the Front Room’s (more info) popular brunch specials and cocktails.
After fueling up, get on the bay through one of Rocky Bottom Fisheries’ lobster boating experiences. Haul and set traps with local lobstermen, either on a private charter or one of the scheduled departures. For those who love getting a taste of Maine from the grocery aisle, head to the Stonewall Kitchen Company Store (more info) in York (more info), about an hour minutes south of Portland, to sample some of the company’s products, do a little shopping, and eat lunch in its kitchen.
Other immersive experiences in the area include a food tour with Maine Day Ventures (more info) or Portland Explorer (more info). Or go biking with Summer Feet (more info) to Portland Head Light (more info) with a lobster roll lunch from a Bite Into Maine food truck (more info). You can also check out Mere Point Oyster Company in Brunswick or go on an a kayak trip with L.L. Bean Outdoor Discovery School (more info) to an oyster farm.
Later in the evening, be as casual or upscale as you want. For fat, juicy lobster rolls, Highroller Lobster Co. (more info) features a more diner-style vibe, and Luke’s Lobster (more info) has a panoramic dockside view.
Meanwhile, the award-winning Công Tử Bột (more info) serves cold bún chả noodles with pork belly and caramel pork patties as well as brined chicken phở gà soup, in a simple setting. The restaurant doesn’t take reservations for parties of three or fewer, so get there early if you want as close to a guaranteed table as possible.
Across the street, Izakaya Minato (more info), an intimate, counter-service spot, serves Maine sea urchin spoons, shio-koji-marinated pork ribs, and an array of sashimi and cooked seafood options. Or head to the Honey Paw (more info) for pan Asian-inspired dishes, like coconutty fried wings, lobster rolls with curry coconut butter, and mapo tofu with local tofu and spicy Sichuan chili.
For an option that opens later, check out Bayside American Café’s (more info) brunch, near the Longfellow Hotel (more info), with avocado toast, lobster scrambles, and a mouthwatering cinnamon bun pancake. Or head to the Munjoy Hill neighborhood for the Front Room’s (more info) popular brunch specials and cocktails.
After fueling up, get on the bay through one of Rocky Bottom Fisheries’ lobster boating experiences. Haul and set traps with local lobstermen, either on a private charter or one of the scheduled departures. For those who love getting a taste of Maine from the grocery aisle, head to the Stonewall Kitchen Company Store (more info) in York (more info), about an hour minutes south of Portland, to sample some of the company’s products, do a little shopping, and eat lunch in its kitchen.
Other immersive experiences in the area include a food tour with Maine Day Ventures (more info) or Portland Explorer (more info). Or go biking with Summer Feet (more info) to Portland Head Light (more info) with a lobster roll lunch from a Bite Into Maine food truck (more info). You can also check out Mere Point Oyster Company in Brunswick or go on an a kayak trip with L.L. Bean Outdoor Discovery School (more info) to an oyster farm.
Later in the evening, be as casual or upscale as you want. For fat, juicy lobster rolls, Highroller Lobster Co. (more info) features a more diner-style vibe, and Luke’s Lobster (more info) has a panoramic dockside view.
Meanwhile, the award-winning Công Tử Bột (more info) serves cold bún chả noodles with pork belly and caramel pork patties as well as brined chicken phở gà soup, in a simple setting. The restaurant doesn’t take reservations for parties of three or fewer, so get there early if you want as close to a guaranteed table as possible.
Across the street, Izakaya Minato (more info), an intimate, counter-service spot, serves Maine sea urchin spoons, shio-koji-marinated pork ribs, and an array of sashimi and cooked seafood options. Or head to the Honey Paw (more info) for pan Asian-inspired dishes, like coconutty fried wings, lobster rolls with curry coconut butter, and mapo tofu with local tofu and spicy Sichuan chili.
Perkins Cove, Maine
Courtesy of Visit Maine
Day 4Boating on One Last Spin Around Casco Bay
Haven’t gotten on the water yet? Now’s your chance. Before heading to the airport, leave your luggage with the hotel and hop on a schooner, a Casco Bay Lines’ mail boat, or another sightseeing charter.
But first, breakfast. Right next to the Francis Hotel is Tandem Coffee and Bakery (more info), a beloved local cafe in a converted 1960s-era gas station. Grab a savory loaded biscuit and a herby lemonade before heading to the docks. For a Maine twist on a national favorite, head to the Holy Donut (more info) to try the potato donut. Every donut there is decadent, but the blueberry maple and whoopie pie flavors are standouts.
But first, breakfast. Right next to the Francis Hotel is Tandem Coffee and Bakery (more info), a beloved local cafe in a converted 1960s-era gas station. Grab a savory loaded biscuit and a herby lemonade before heading to the docks. For a Maine twist on a national favorite, head to the Holy Donut (more info) to try the potato donut. Every donut there is decadent, but the blueberry maple and whoopie pie flavors are standouts.
