When planning a Portland, Maine itinerary, there are so many options it can be hard to narrow things down! The city is known for it’s restaurant and bar scene, downtown shopping area, historic cobblestone streets in Old Port, and activities along the waterfront. Don’t get it confused with it’s famous West Coast counterpart in Oregon, both of which got their name from the Isle of Portland in England.

Portland is the most populous city in Maine, with just under 550,000 people living in the Greater Portland Metro (just under 70,000 in the city proper). It’s also the state’s economic capital thanks to its popularity with summer tourism and being the home to the largest port in the state. You’ll notice during your visit that many of the buildings are built with brick, because the entire city actually burnt down during the Great Fire of 1866! When they rebuilt, they opted for brick instead of wood to avoid similar future disasters.

Don’t miss the rest of my Portland food and drink recommendations, as well as all the different coffee shops we crammed into 48 hours!

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Know Before You Go

Weather in the Spring and Fall can be unpredictable, with a mix of sunny and rainy days and mild to chilly temperatures. Summers are warm, with temperatures in the 70s and 80s. The city tends to get a significant amount of snow in the Winter months.
November through April is considered Portland’s off-season. Many tourist attractions are closed during this part of the year.
Prices (as well as crowds) go up drastically during the tourist-heavy summer months.
Portland has a LOT of cobblestone streets and sidewalks in the downtown area, which could be hard to navigate in heels. Bring a comfortable pair of shoes!

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Getting Around

Flying

Located about 2 miles from Downtown Portland is Portland International Jetport. Unsurprisingly it is the busiest airport in the state, serving over 2 million passengers a year. It’s definitely on the smaller side, with just a single terminal and 11 gates. A few of the airlines that fly into the airport include American, United, Delta, Frontier, JetBlue, and Southwest.

Trains and Buses

East of the airport, across the Fore River, is the Portland Transportation Center. It is a relatively small station, with a seating area, vending machines, a ticketing counter, and restrooms. In terms of trains, there’s just one option: the Amtrak Downeaster. The train line makes 5 daily round-trips between Boston, MA and Brunswick, ME. The ride from Boston to Portland takes about 3 hours and passes by some beautiful beach communities! A number of buses also operate out of the transportation center, predominantly through Concord Coach Lines but also a few Megabuses as well.

For getting around the city, the Greater Portland Transit District METRO operates a number of bus routes that service the Downtown area, as well as surrounding towns. As of 2025, fare for local routes is $2 for one ride or $6 daily.

Driving

If you’re driving, there is a good amount of street parking and public parking lots scattered throughout downtown. It was fairly easy to find parking when we went in the spring, but it’s likely significantly harder to come by in the tourist-heavy summer months. Street parking is generally free after 6 pm, as well as all day on Sundays and major holidays. Walking, or or taking an Uber when necessary, is probably going to be the easiest option!

Visit Portland has a much more in-depth rundown of all the available transportation options you’ll have at your disposal.

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Portland Itinerary | Day 1

If you plan to follow this Portland Maine Day 1 itinerary, be prepared to get your steps in! It crisscrosses across the city a bit more than you will on Day 2.

Breakfast at Tandem Coffee + Bakery

Inside of a converted 1960’s gas station on the west side of town you’ll find Tandem Coffee + Bakery. They’re known for their baked goods, especially their loaded biscuit sandwiches (both sweet and savory options available). Don’t be deterred by the line – it’s almost constant but moves pretty quickly! I was a bit worried we wouldn’t be able to find somewhere to sit, but there are plenty of spots both inside and out.

742 Congress Street

Do Some Shopping in the Arts District

Walk off your breakfast with some shopping! If you’re visiting on a Friday, you could also head back this way in the evening for the First Friday Art Walk from 5-8 pm. Local artists line the streets and galleries open to the public, some with food and drinks.

Red Squirrel Maine – 647A Congress Square.
Vintage and locally made decor, home goods, and clothes.

Green Hand Bookshop – 661 Congress Square.
Independently owned bookstore packed full of all different genres of used books.

Soleil – 550 Congress Street.
Bright and airy shop filled with home goods and gifts (plus an Inciardi Prints vending machine, which I’m obsessed with).

Two Fat Cats Bakery – 175 Spring Street Unit C.
American-style scratch bakery specializing in cookies, pies, and woopie pies.

Weekend Vintage – 184 State Street.
Small boutique stocked with a variety of vintage clothing and accessories.

Lunch at Eventide Oyster Co.

No stop in Portland is complete without getting a lobster roll. While there are plenty of options to choose from, we went with Eventide Oyster Co. Unlike any of the other times I’ve had a lobster roll in the past, Eventide actually serves theirs warm. Similar to many other restaurants in the area, the food comes out of the kitchen as it’s ready so sharing is recommended. Otherwise your group will likely be eating at different times! Not a lobster person? The menu also includes fish sandwiches, oysters, and New England clam chowder just to name a few.

86 Middle Street

Allagash Brewing Tour

If you’ve been to a bar in the Northeast, there’s a good chance you’ve seen Allagash Brewing on the menu – specifically the Allagash White. This wheat beer accounts for 80% of all the brewery’s sales! Beer lovers have two different tour options: the Taste of Allagash (a 30 min brewery and barrel room tour that includes 2 samples) or the Signature Beer & Barrels Experience (an hour long brewery and Cellars tour with 5 samples focusing on wilds & sours). I took the Signature tour and loved being able to try unique beers you can only get on-site. Even my friend who isn’t a huge beer drinker went home with a few fruited/sour bottles!

50 Industrial Way

Dinner at Fore Street Restaurant

Located inside a renovated warehouse on its namesake street, Fore Street is an upscale American restaurant with a cozy brick filled interior with a wood-fire grill and oven. Their menu is always changing slightly based on what ingredients are available and in season. Wine lovers will also be thrilled by their large wine selection. They keep bar seating and a few tables available for walk-ins but I’d definitely make a reservation, especially on the weekend!

288 Fore Street

Drinks at Blyth & Burrows

An upscale cocktail bar with a maritime theme, Blyth & Burrows is technically two bars in one! In the back of the bar you’ll find a bookcase, behind which is the entrance to a second floor ‘speakeasy’. According to the bartender it has a completely different vibe and decor, but unfortunately we had to take her word for it as it’s not open on weekdays in the offseason. Be sure to order one of their house-made bottled carbonated cocktails! I personally recommend the Sleight of Hand.

26 Exchange Street

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Looking to add more to your Portland, Maine trip itinerary?
Check out these exciting options:

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Portland Itinerary | Day 2

Our Day 2 Portland Maine Itinerary focuses mainly on Old Port and the waterfront, plus a quick trip out to the famous Portland Head Lighthouse.

Breakfast at Bread & Friends

Breakfast and brunch at Bread & Friends is first-come, first-served, so I’d recommend getting here early because they get BUSY. I kept seeing this place all over social media and it truly lived up to the hype. Their menu focuses on baked goods, brunch dishes, and delicious coffee. Everything is suggested to be shared, which we didn’t really take seriously and ended up with way too much food for two people! Everything brought out to the tables around us looked so good, I wish I’d been able to try more.

505 Fore Street

City and Lighthouse Trolley Tour

I’m normally not much of a guided tour person, but was glad we gave the Portland Discovery Land & Sea City and Lighthouse trolley tour a shot. Talk about the driver who is a Portland native, and a writer whos book we ended up buying afterwards! The entire tour was about an hour and a half, including 30 minutes to wander around at Portland Head Light. It’s located in nearby Cape Elizabeth, and is oldest lighthouse in Maine. It’s also believed to be the most photographed lighthouse in the United States. Photos from inside the trolley are unfortunately a bit hard to come by in the case of bad weather, thanks to the thick plastic covering the windows.

170 Commercial Street

Try a Potato Donut from Holy Donut

After such a large breakfast, a snack may be in order instead lunch. Which means it’s the perfect time for a pitstop at the Holy Donut! This family owned business initially started out when a mother wanted to try and make a healthier donut for her child. They’ve since expanded to 5 locations across Maine. Keep in mind they close once they sell out, and it’s recommended you arrive before noon if you want the largest selection to choose from. They’ve also started shipping nationwide so you can enjoy their donuts after you get back from your trip (but I will say, that option is a bit pricey).

177 Commercial Street

Shopping in Old Port

There are so many cute shops in the Old Port district and along the waterfront, so a second round of shopping is definitely necessary. Whether you’re into super touristy gift shops, bookstores, or vintage finds, there’s a little something for everyone.

Sherman’s Maine Coast Book Shop – 49 Exchange Street.
If the front signage is to be believed, this is Maine’s oldest bookstore!

Sea Bags Flagship Store – 123 Commercial Street.
Bags and accessories made out of recycled cloth from boat sails.

Blanche + Mimi – 195 Commercial Street.
A store so packed with housewares, toys, and gifts, I almost didn’t even know where to look!

Meowy Jane – 3 Market Street.
Cat themed recreational cannabis dispensary (must be 21+ to enter, cash only).

Fore & Wharf – 446 Fore Street.
New England-inspired clothing and accessories boutique.

Danforth Pewter Portland – 111 Commercial Street.
Hand crafted gifts from New England artisans including jewelry, vases, and Christmas ornaments.

Dinner at Via Vecchia

Situated on a cobblestone street in Old Port, you’ll know Via Vecchia by its ivy-covered brick exterior. This small plates Italian inspired restaurant and wine bar features moody lighting and delicious pasta. Service is a 10/10 – attentive without being intrusive or making you feel rushed. Everything we ordered was amazing, but I still think about the focaccia and campanelle with shrimp in particular.

10 Dana Street

Drinks at Room for Improvement

If you’re looking for “a halfway decent bar” (their words, not mine), Room for Improvement is the place to go. At this cozy neighborhood cocktail bar you can get the typical beer, picklebacks, and hotdogs, as well as their own creative takes on classic cocktails, like a white negroni or Harvey Wallbanger. This was probably my favorite bar we stopped in while visiting Portland!

41 Wharf Street

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Additional Activity Ideas

Looking to expand your Portland Maine itinerary to 3-4 days, or visiting during the summer? Below are some things we didn’t get to or weren’t yet open for the season when we visited in late spring.

Lobstering Tour with Lucky Catch Cruises – 170 Commercial Street.
On these 80-90 minute cruises around Casco Bay, you can either participate or just go for the views/experience. You can also book private excursions for special occasions!

Wine Sails with Wine Wise Events – Maine State Pier at 56 Commercial Street.
Love wine and being on the water? Wine Wise offers a variety of different wine-focused experiences from mid-June through mid-October, some with food or even sunset views. These cruises are very popular and sell out fast, so book early.

Casco Bay Islands Ferry – Maine State Pier at 56 Commercial Street.
This is open year-round, we just didn’t have enough time! Take a trip out to one of the 7 surrounding islands, or just spend some time on the water with one of their specialty cruises. During the summers they also have a cruising concert series.

Climb to the Top of the Portland Observatory – 138 Congress Street.
This 7 story historic signal tower was built in 1807 and is the last of its kind in the United States. It was designated as a National Historic Landmark.

Visit the Portland Museum of Art – 7 Congress Square.
The largest and oldest public art institution in all of Maine houses a variety of American, European, and Contemporary art pieces.

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Hotels

Most people prefer to stay in Old Port and the downtown waterfront area, in order to be close to all the restaurants, bars, and shopping. You’ll find a mix of well known chains as well as some smaller boutique hotel options.

Where We Stayed

Holiday Inn Portland – By the Bay
88 Spring Street, Portland, ME 04101
While not the most beautiful or modern hotel, it’s clean and gets the job done (especially when you don’t plan to spend much time in the room). We didn’t have the greatest view from our room on the 4th floor, mainly the roof with AC units, but you’re close enough to see the bay. A plus? The cost to park in their lot was half as much as the other hotels we considered. As of Spring 2025 they were in the middle of renovating the lobby and on-site restaurant.

Other Nearby Options

Looking for more hotel options? Below are other nearby hotels that we considered while planning our own Portland trip. They’re all still located within the downtown area near the waterfront.

Courtyard Portland Downtown/Waterfront
321 Commercial Street, Portland, ME 04101

The Press Hotel
119 Exchange Street, Portland, ME 04101

Hilton Garden Inn Portland Downtown Waterfront
65 Commercial Street, Portland, ME 04101

Aloft Portland Downtown Waterfront ME
379 Commercial Street, Portland, ME 04101

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What‘s a must-see for my next Portland, Maine trip? Let me know in the comments!