Portland, Maine: Perfect Weekend Itinerary

3 Days in Portland, Maine: The Perfect Weekend Itinerary

Portland, Oregon, tends to be the more famous of the two Portlands, but for Mainers, Portland, Maine, is the big city. Filled with rich history, scenic parks, and an incredible food and drink scene, this Portland more than deserves a trip.

If you’re planning a 3-day weekend in Portland, Maine, you’ll likely want to arrive between late spring and early fall. Although summer is the peak of tourist season, you’ll find that much of Portland shuts down when the weather turns cold. So many of the top attractions in the city may not be open if you arrive later in fall or winter.

Plus, with Portland being a coastal city, you’ll likely want to take advantage of the beautiful coastline and nearby islands when the weather is nice enough. And summer is also when you’ll find the most events and festivals. June brings about Portland Wine Week, while nearby Yarmouth holds its annual clam festival in July, and you can enjoy the famous Maine lobsters at their own festival in nearby Rockland in August.

Planning a weekend in Portland? We’ve put together a Portland itinerary to help you see the very best of the city in just three days. Stick to this list, and you’re bound to have an incredible time on your coastal getaway!

Please keep in mind that this Portland, Maine, itinerary assumes that your three days in the city begin on a Friday, as there are time-sensitive activities on this list. The Portland Museum of Art is not open on Monday, and therefore, you cannot visit this stop if your last day is Monday. Additionally, the farmers’ market, which you’ll see on your second day, is only open on Wednesdays and Saturdays. 

If you’re still deciding where to stay then make sure to check out our article on the cool boutique hotels in Portland, Maine!

How to Spend a Weekend in Portland, Maine

Getting Around Portland

Getting Around Portland, Maine: The Perfect Weekend Itinerary

If you’re arriving in Portland via plane, the most convenient airport is the Portland International Jetport, not to be confused with Portland International Airport, which will take you to the other city of the same name in Oregon. The Portland International Jetport is just 2 miles from Downtown Portland, making it easy to start your 3-day weekend in Portland, Maine, when you arrive here.

From there, you have several options. To start your trip, you can take Route #5 of the METRO’s bus service to get to the downtown area. If you choose to rely on public transportation during your 3 days in Portland, you’ll be taking the METRO quite a bit, as it makes it easy to get to many of the top destinations in Portland. 

However, it’s worth considering getting a rental car in Portland. While you won’t need it to get around the downtown area, you may want it if you plan on venturing further out. Uber and Lyft do operate in Portland, but service can be spotty and slow. Plus, taxis aren’t always easy to find. So, if you’re without a rental car and want to go somewhere that’s difficult to get to with public transportation, you may be waiting for a while to get a ride. 

If you have more than 3 days in Portland, you should definitely consider getting a rental car, especially if you want to venture outside of the city proper. Portland has many day-trip options. If you want to visit a major city, Boston is under two hours away by car, but you can also check out smaller cities with unique offerings. 

Rockland in Maine, for instance, is a great place to visit for its quaint arts scene, while you can’t beat Salem in Massachusetts if you’re visiting during the spooky season. And Acadia National Park is only 3 hours away by car for those looking to experience scenic hiking and other outdoor adventures.

Explore Portland on a Trolley Tour


Portland, Maine Itinerary – Day 1

Explore Old Port

3 Days in Portland, Maine Itinerary: Old Port

You’re going to start your 3 days in Portland, Maine, at the heart of the city, the Old Port. Here, you’ll find cobblestone streets that will transport you back in time as you venture past 18th- and 19th-century buildings that now house some of the best dining, drinking, and other attractions you’ll find in Portland. 

Breakfast at The Holy Donut

Portland, Maine 3 Day Itinerary Weekend Guide: The Holy Donut

Before you get started exploring, you’re going to need to fuel up. And we can’t think of a better way to do it than by chowing down on one of the best doughnuts in the Northeast, which can be found at The Holy Donut

These massive doughnuts are made with potatoes, making them rather hearty and filling. If you can only eat one, we highly recommend the Maple Bacon, the Blueberry Holy Cannoli, or the Honey Lavender. Or you can buy all three and split them with your fellow travelers because, trust me, these doughnuts are too rich to try and eat three at a time by yourself!

Learn All About Maine Lobsters on a Cruise

Weekend in Portland, Maine 3 Days Itinerary: Lobsters

Next up, you’re going to do something that you can only really do in Portland. Maine is famous for its lobsters, so you’re first activity is to learn just where they come from. Lucky Catch Cruises offers the chance to climb aboard a lobster boat and see it in action. Keep in mind that this cruise tends to sell out, so be sure to get your tickets in advance.

You’ll venture out on the waters of Casco Bay, where you’ll be guided through the day-to-day of a real Maine lobsterman. How much you participate is up to you. You can just enjoy taking in the sights, or you can help haul up the traps yourself. 

No matter which you choose, you’ll also get to enjoy listening to a knowledgeable guide who will tell you all about the history of Maine’s lobster scene, today’s conservation efforts, and little-known facts about your favorite crustacean!

3 Days in Portland, Maine Weekend Itinerary: Lobsters

Once your cruise comes to an end, you have the option to buy the lobster you catch at a reduced price than what you’ll find elsewhere. Didn’t catch anything? No problem. 

The tour company also keeps a fresh supply for visitors, just in case. If you do decide to purchase one, you can bring it home to cook yourself, or you can turn the lobster into your lunch by venturing over to the Portland Lobster Company, where they’ll cook it up for you. 

Didn’t buy a lobster? We have another great lunch option for you. Stay in Old Port and head on over to Duckfat. If you’re a poutine fan, you’ll hardly find a better place for it than this local favorite. 

The gravy is made from scratch with roasted duck bones, while the cheese curds are locally made. No matter if you’re getting the poutine or simply an order of their incredible fries, they’re always made in true Belgian style and fried in the restaurant’s signature duck fat. 

Discover the Best of Portland Food

Go Brewery Hopping

Weekend in Portland, Maine: Brewery Hopping

Hopefully, you didn’t fill up too much because your next activity is a tour of Portland’s famous brewery scene. Did you know that Portland has the most breweries per capita of any US city? It has 18 breweries for every 50,000 people. For some comparison, the other Portland, which is also considered a top place for brewery lovers, only has nine for every 50,000 people. 

Maine Brews Cruise can help you see some of the best breweries Portland has to offer. If you want to stick around Old Port, you can take their Old Port Walk, Talk, & Taste Tour, which is as focused on the craft beer scene as it is on Portland’s history. While you stroll along with your guide, you’ll learn about important Portland landmarks, like the US Custom House, the Workingmen’s Club, and the Mariners’ Church. 

From there, you’ll make your way to three of Portland’s top breweries: Shipyard Brewing Company, Gritty McDuff’s, and Liquid Riot Bottling Company. Included in your ticket price are samples of craft beer and hard seltzer at the three locations, as well as a snack at one location.

Visit Portland’s Breweries

Go Shopping in Old Port

3 Days in Portland, Maine Itinerary: Shopping in Old Port

Depending on when your tour is, you should either do some shopping around Old Port before or after. Old Port is filled with charming boutiques and storefronts, especially if you want to experience Portland’s food scene. Over on Fore Street, you’ll find the Old Port Candy Co., famous for its fresh fudge and chocolate. It’s a must-do on any Portland, Maine, itinerary if you have a sweet tooth!

Or, for an even more unique option, visit Washington Avenue’s Onggi Ferments + Foods. This market, bakery, and cafe specializes in all things fermented, believing deeply in the health and flavor benefits of fermentation. Whether you want to learn to ferment yourself or just want to chow down on some fermentation-forward treats, like sourdough chocolate chip cookies and matcha and black sesame butter mochi, Onggi is worth a stop. 

Dinner at Eventide Oyster Co.

Portland, Maine 3 Day Itinerary Weekend Guide: Eventide Oyster Co.

When you’re ready for dinner, head over to Eventide Oyster Co. Hopefully, you’re not too lobstered out from your morning cruise to enjoy Eventide’s famous brown-butter lobster roll. But if you are, there’s plenty more to enjoy at this oyster bar.

You’ll find oysters aplenty on this menu, as well as many more seafood options. From clam bakes to their signature scallop waffle-yaki, there’s so much to choose from. The same goes for their extensive drink menu. The hardest part of eating and drinking here is trying to make up your mind on what to order.


Portland, Maine Itinerary – Day 2

Visit the Portland Farmers’ Market

3 Days in Portland, Maine Weekend Itinerary: Farmers Market

Start the second day of your weekend in Portland, Maine, feeling like a local by visiting the Portland Farmers’ Market. Held in Deering Oaks Park, this farmers’ market is where you’ll find over 40 of Maine’s best farmers and food producers. 

From fresh berries and oysters to cheese and maple syrup, there’s a little bit of everything to try here. Sample your way around the market and help support local farmers in a beautiful setting. 

If sampling the market’s treats didn’t fill you up, take a short stroll over to the Bayside American Cafe, a cozy spot that’s famous for its brunch offerings. From homemade corned beef hash to buttermilk pancakes stuffed with cheddar, bacon, and scallions, Bayside turns classic American breakfast dishes into new and inventive options that are bound to leave you stuffed and satisfied. 

If you’re an eggs benedict fan, you have eight different variations to try, from a Cajun-inspired benedict to one served with famous Maine lobster. Don’t forget to grab yourself one of their innovative cocktails to go alongside your breakfast!

Tour the Portland Observatory 

From there, catch a bus or enjoy a leisurely walk to the Portland Observatory, a historic landmark that offers one of the most incredible views of the city. The 86-foot octagonal tower was built in 1807 and is today the last remaining maritime signal town in the US. 

You’ll find the tower over on Congress Street, where 45-minute guided tours run every half hour from Thursdays through Mondays. On your tour, you’ll be able to climb the long and winding stairs to the top. 

There are just over 100 steps to climb, and there is no elevator to reach the top, so this activity may not be an option for those unable to make that trek. But if you can reach the top, the view is well worth it.

Lunch at Navis Cafe

3 Days in Portland, Maine Itinerary: Navis Cafe

For lunch, stop by Navis Cafe, which offers hearty sandwiches and all-day breakfast options. From lobster rolls to ham, egg, and cheese bagels, it’s comfort food at its finest. Grab a cold brew or a craft beer and make yourself at home in this cozy cafe. 

Explore the Maine Narrow Gauge Railroad Co. and Museum

Portland, Maine 3 Day Itinerary Weekend Guide: Maine Narrow Gauge Railroad Co. and Museum

Just a short stroll away is the Maine Narrow Gauge Railroad Co. and Museum. This unique museum focuses on preserving the history of Maine’s railroading heritage. But it’s much more than a museum.

Here, you can take a ride in a vintage train car, enjoying the beautiful scenery sweeping past you. Your journey also includes onboard narration that will tell you all about Maine’s railroading history, as well as the history of the landmarks you’re going past. 

Since you’re visiting on a Saturday, you can take the Sunset Express, assuming you’re planning your weekend in Portland in the summer. On summer Saturday evenings, the Sunset Express allows you to take in the usual route with all its beautiful sights, with the added benefit of seeing it all as the sun begins to set. 

Plus, all passengers get a complimentary beverage. Adults can partake in craft beer, hard seltzers, or wine, while little ones also get their pick of alcohol-free drinks.

Dinner at The Front Room

3 Days in Portland, Maine Weekend Itinerary: The Front Room

For dinner, head over to The Front Room, a true Portland hidden gem. This neighborhood gathering spot is quaint and comfortable, almost as comfortable as the comfort food on the menu. From burgers to carbonara to duck breast, there’s a little bit of everything on the menu, so you can guarantee that every member of your party will find something to fall in love with.


Portland, Maine Itinerary – Day 3

Breakfast at Two Fat Cats Bakery

Weekend in Portland, Maine 3 Days Itinerary: Two Fat Cats Bakery

To start the last day of your 3 days in Portland, Maine, you’re going to visit one of the best bakeries in the city: Two Fat Cats Bakery. This shop specializes in fresh baked sweets made with real butter, local eggs, and other locally-grown ingredients. Stop in for breakfast and help yourself to a delicious treat, like their Blueberry Buckle, a New England-style cake-like pastry made with wild Maine blueberries and a brown sugar and oat streusel topping. 

Is it too early for a whoopie pie? We’re inclined to say the only acceptable answer is: “Never!” It’s never a bad time to get this classic Maine dessert. If they’re available, be sure to get one of their whoopie pies. 

The traditional one comes with two moist chocolate cake rounds with vanilla buttercream sandwiched between. But there are also seasonal options, like their lemon zucchini cakes with wild Maine blueberry filling. You absolutely can’t leave Portland without getting yourself a whoopie pie.

Peruse the Portland Museum of Art

Now, you’re fueled up to start your day, so stroll on over to the Portland Museum of Art. As the oldest and largest art museum in Maine, they claim that it would take you nearly 10 years before you could see everything in their collection. While you don’t have 10 years and you only have 3 days in Portland, you should still stop in to see all that you can. 

The museum’s permanent collection includes everything from American and European artwork to pottery and silverware collected throughout time. You’ll find both local artists on display, as well as works by some of the greatest artists of all time, like Claude Monet and Winslow Homer.

This museum also hosts numerous events, so you never know what will be going on when you visit. From film screenings to artist talks to workshops, a morning at the Portland Museum of Art is always well spent.

Lunch at Artemisia Cafe

Portland, Maine 3 Day Itinerary Weekend Guide: Artemisia Cafe

Next, get lunch at the Artemisia Cafe, which serves brunch until 2 pm on Sundays. Their menu is packed with traditional brunch favorites done right. 

If you’re in the mood to go the breakfast route, you can choose between options like French toast, breakfast burritos, and vegetarian hash. If you’re more in the mood for lunch, you can dine on burgers, salads, and sandwiches. Or get the best of both worlds with the egg-topped Brunch Burger.

Go Back in Time at the Victoria Mansion

3 Days in Portland, Maine Weekend Itinerary: Victoria Mansion

Your next stop is a historic landmark you’re not going to want to miss. The Victoria Mansion was built between 1858 and 1860 and is considered one of the best-preserved examples of pre-Civil War architecture in the US. 

Though the outside is stunning, you can also venture inside, where you’ll see the hand-painted murals, marble fireplaces, and intricately-carved woodwork throughout. Ninety percent of the original furnishings are still on display, which really helps transport you back in time.

If you decide to take a guided tour, they run every 20 minutes, with tours lasting between 45 and 55 minutes. While some days offer self-paced tours, other days only allow docent-led tours, so you may have to take a guided tour on the day you visit. 

Be sure to purchase your tickets in advance and check the website’s calendar to learn if you’re visiting on a day when you’re allowed to do a self-guided tour or if you’ll need to take a docent-led tour.

Admire Victoria Mansion

Set Sail with Portland Schooner Co.

Weekend in Portland, Maine 3 Days Itinerary: Portland Schooner Co.

After you tour the mansion, venture back to the Old Port region for the last activity of your weekend in Portland. The Portland Schooner Co. offers sails on a Maine-crafted wooden schooner. 

While you will have a knowledgeable captain and crew to guide you, there’s no narration, and it isn’t so much a tour as it is simply a relaxing, scenic experience. You’ll be able to sit back and enjoy the ride as you watch the coastline go by. 

The company has two-hour-long sails throughout the day, but it’s hard to find a better time to go out on the water than at sunset. Their sunset sails occur as early as 4 pm or as late as 6 pm, so be sure to check the website to make sure you don’t miss your departure time.

Dinner at Street & Co.

Weekend in Portland, Maine 3 Days Itinerary: Street & Co.

Next up, grab dinner at Street & Co. over on Wharf Street. You already know that lobster is famous in Maine, but did you know that scallops are another specialty? Street & Co. is where to get some of the best scallops in Portland. 

This bistro-style restaurant is all seafood, all the time. All ingredients come from local fishermen and farmers. If you’d rather skip the scallops, you can also get lobster here, as well as mussels, clams, shrimp, and many different kinds of fish. 

The restaurant also has one of the best wine and cocktail lists in the city, and their innovative dessert menu is delightful. Their Limoncello Mousse makes for a great way to end your weekend in Portland, Maine!


More Places to Eat & Drink in Portland, Maine

Drink and play at Arcadia:
Named for the Acadia National Park, this arcade bar is perfect for date night. Share some cocktails while you challenge each other to beat your pinball scores. There’s even a monthly board game night if you’re more into analog fun.

Try Maine classics at Fore Street:

3 Days in Portland, Maine Itinerary: Fore Street

Made with only local ingredients, the dishes on this upscale restaurant’s menu change daily depending on what’s in season and what the local farmers, fishermen, and foragers can provide. But it’s always serving Maine favorites, like oysters and mussels.

Split small plates at Central Provisions:

Portland, Maine 3 Day Itinerary Weekend Guide: Central Provisions

This rustic restaurant is designed for groups to share both food and drinks as well as conversation. You’ll find plenty of unique offerings on the menu, like pear wine and sheepmilk cheese.


What to Do If You Have More Than 3 Days in Portland, Maine

Eastern Promenade Trail

3 Days in Portland, Maine Weekend Itinerary: Eastern Promenade

Walk along the Eastern Promenade Trail. The Eastern Promenade is a scenic 68-acre park right on the waterfront, featuring several hiking and walking trails. The Eastern Promenade Trail was an old railway line that’s easy to follow and takes you right through the heart of the park.  

Cape Elizabeth

Weekend in Portland, Maine 3 Days Itinerary: Portland Head Light

See the lighthouses in Cape Elizabeth. Cape Elizabeth is home to stunning views, a tranquil beach, and two of Portland’s most well-known lighthouses. The Two Lights and the Portland Head Light are each famous in their own right, though the latter is actually the most photographed lighthouse in the world! 

See the Lighthouses of Portland

Peaks Island

Weekend in Portland, Maine: Peaks Island

Take the ferry to Peaks Island. Portland is surrounded by small islands, with Peaks Island being the most popular of them. Hop on the ferry and then spend the day enjoying the island’s beaches, galleries, and museums.

Mailboat Run

Take the Mailboat Run. The Mailboat Run offered by Casco Bay Lines is a ferry that delivers mail to the islands around Casco Bay, and it’s one of the most unique things to do around Portland. It’s also a great way to see the other islands outside of Peaks Island.

Acadia National Park

3 Days in Portland, Maine Itinerary: Acadia National Park

Visit Acadia National Park. About 3 hours away by car, Acadia is one of the best day trips from Portland. There’s a reason why it’s one of the top 10 most visited national parks in the US. Here you can go hiking, biking, stargazing, tide-pooling, kayaking, swimming, and see historic landmarks.

Discover the Best of Acadia National Park 

We hope you enjoy your weekend trip to Portland, Maine! Should we add something else to our 3-day Portland, Maine itinerary? Let us know in the comments.


Planning a trip to Maine? Check out our favorite travel guides and resources!


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Author

  • Jacqueline Gualtieri

    Jacqueline is a writer and editor pursuing the freelance life to explore the world. Born and raised in New Jersey, she spent her college years in Boston before settling down with her partner and puppy in Monterey, California.

    When she’s not writing, you can often find her planning her next trip. Road trips are her favorite, whether it’s driving across the country or simply exploring a new city in her own backyard. She loves uncovering the history of every new place she goes.

    Jacqueline has a restless passion for learning and makes it a goal to pick up a new skill every year. She’s picked up embroidery, crocheting, knitting, and cross-stitching, but she’s hoping to master more languages to help her in her travels. She’s also a published author, with short stories and poetry appearing in several anthologies.

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