Best Things to Do in Portland in 3 Days – Maine


Are you planning your Portland itinerary and wondering about the best things to do in Portland in 3 days? Then read on and find many travel tips for your trip!

This post was written by Cassandra.

Portland, Maine, is a lovely historic harbor filled with New England Charm. It’s the perfect addition to an East Coast road trip, the halfway point on a car trip up to Canada, or a weekend stop all on its own.

Art district, foodie town, micro-breweries, colonial history, and dramatic coastlines, this quaint city has a bit of everything.

Founded in the 1630s as a fishing and trading port, much of the area’s roots are still visible, and just outside the city, there’s plenty of Maine’s raw natural beauty to be seen! From lush evergreen forests to migrating humpback whales along the coast and nearby skiing resorts, the options are endless. 


Let’s start with some travel tips for your trip.

How to Arrive

  • PWM is the main airport if you are flying in.
  • The city is also easily accessible via car from southeast Canada or other northeast US points as well as train from other major east coast cities. 

How to Get Around Portland

Portland is a very walkable city and is also bike-friendly as well! If you’re going a bit further taxi services, ride shares like Uber and the Metro Bus system are also available. 

Best Time to Visit

The best to visit Portland would be in summer or in fall. Summer is my favorite with warmer weather outdoor activities galore, plus it’s humpback season as the whales migrate up for the summer. Fall is a popular time to visit, though, since Maine is known for its gorgeous colorful autumn foliage. 

Winter is only great if you are looking to partake in winter sports like skiing or snowboarding! Otherwise, it’s best to avoid the harsh winters.

Where to Stay

The downtown and harborside areas are the best spots to be in, and there are plenty of hotels to choose from. Some of my favorites are

  • The Press Hotel
  •  The Francis
  • The Danforth
  •  and Portland Regency

Of course, there are the usual American chain brands here as well, but in my opinion, part of the New England charm is to stay in a classic New England hotel usually set in a restored historic building.

Tips for Solo Female/Security

Portland is a very safe and friendly city! Like anywhere else, be aware of your surroundings.

  • Don’t make strangers aware that you are traveling solo, or provide your accommodation info.
  • After dark, you can always opt for Uber or taxi instead of walking especially if you’ve been drinking!
  • Keep any valuables or bigger sums of money out of sight. 

Costs for Visiting

Like most cities in the US, Portland can be pricey but still much more affordable than its larger counterparts like NYC.

Average entrees would fall around $15 per person, for example. Some museums are free others may charge an entry fee. Whale watching would be around $50 per person, whereas a seal watch or lighthouse cruise tour would be around $20 per person.  


Portland is a foodies paradise, brimming with breweries, wine bars, cafes, and a wide variety of restaurants – many being a farm to the table, there’s an endless selection of choices.

Some of my favorites are the Tandem Coffee and Bakery, Central Provisions, Drifter’s Wife (wine bar), Alagash Brewery, The Holy Donut, Artemisia Café, and The Gelato Fiasco.

Portland, Maine


With 3 days in Portland, you can see the main sights and spend time in nature.

Day 1 in Portland

The first day is perfect for just exploring leisurely on foot.

Tandem Coffee and Bakery

Start with a bite to eat at the Tandem Coffee and Bakery. They roast all their beans on-site and have all the taste of bakery classics. I recommend the cinnamon buns!

Portland Museum of Art

Portland is a city filled with artists and art schools, so it’s a great spot to enjoy museums and galleries! From the Tandem Coffee and Bakery, head to the Portland Museum of Art.

They have displays in all art styles and mediums, including rotating exhibitions and events. Take a peek at their website beforehand to see what’s currently on display.

Freedom Trail

After having your fill at the museum, take a self-guided tour of the Freedom Trail, which is one of the best things to do in Portland in 3 days.

Portland Freedom Trail a must in 3 days

This is a famous historic trial in the American abolitionist movement.  Along the way, learn the story of thousands of men, women, and children who escaped slavery and the abolitionists who helped operate the Underground Railroad.

  • Be sure to download or print out the map offline beforehand.

Portland Observatory

Working your way through historic downtown, head towards the Portland Observatory – a former maritime signaling tower now perfect for taking in the views of the bay and its islands.

Portland Observatory on any Portland 3-day itinerary

This is the last standing maritime signaling tower in the US! Climb to the top and soak it all in before heading to Drifter’s Wife.

Drifter’s Wife

Drifter’s Wife started as a wine shop and bar to showcase natural wines and evolved to include an amazing restaurant that creates meals perfectly paired with the wines. It’s the ideal stop for a delicious meal and some wine to end the day.

Day 2 in Portland

For day 2 in Portland, these are my suggestions.

Water taxis and boats on the busy Maine Wharf, Portland, Maine

Becky’s Diner

Start your morning with a hearty breakfast at Becky’s Diner.

Becky’s is a traditional American dinner on the waterfront that opened in the 1990s. It’s a charming family-run business serving up all the classics and definitely worth a stop during your stay!

Victoria Mansion

From here, head to the Victoria Mansion. It’s an absolutely gorgeous place to visit in 3 days in Portland and only a short walk from the diner.

Victoria Mansion, also known as the Morse-Libby House or Morse-Libby Mansion

Victoria Mansion is a stunning home that has been restored and maintained so you can step back in time with a visit.

It was built in the mid-1800s and was saved and opened to the public in the 1940s. It’s currently open 10 AM -3:45 PM daily, and it’s a unique sight in Portland.

Great there at the opening so that you can enjoy it without crowds.

Old Port District

Afterward, head to the Old Port district and join the Portland Craft Drink tour!

Portland Old Port is one of the best places to visit

This brew bus is a fun way to explore all the amazing breweries in the city. If you started at the mansion at 10, you could catch the 11 AM Brew Bus; it lasts about 3 hours. You can get your tickets in advance via Viator.

The Brew Bus visits 3 breweries plus a stop at Union Kitchen for a bite to eat- if you miss the 11 AM, another runs at 2:30 PM.

Holy Donuts

When you wrap up-, grab a snack at Holy Donuts, Holy Donuts is an icon in Portland and makes the most amazing donuts fresh, from scratch, and all-natural. The donuts are made with Maine potatoes and come in a variety of flavors. My favorite is the berry glaze.

Fort Allen Park

Get your donut to go and from here, walk out to Fort Allen Park for lovely waterfront views. This is a nice grassy area facing the sea with a gazebo and benches- the perfect spot to sit and have your donut while taking in the views.

Fort Allen Park in Portland, Maine, USA is one of the best things to see in 3 days

Portland Paddles Kayak

From here, you can join one of the Portland Paddles kayaking tours. They have a few tour options and SUP, but if you prefer to self-explore, you can always rent a kayak and enjoy the time on your own.

By the time you finish exploring Portland from the waterside, you’ll have worked up an appetite!

Central Provisions

Central Provisions is the perfect place to sit down for a delicious meal- one of the must-eats of Portland’s foodie highlights- make sure you save some room for dessert so you can head over to Gelato Fiasco for some homemade gelato.

The flavors can rotate, but if available, I recommend anything made with Maine’s wild blueberries. 

Day 3 in Portland

Today is the time to experience the overwhelming natural beauty – do not skip this part of your Portland itinerary.

Portland in 3 days

Odyssey Whale Watch

Start with a morning whale watch. Between late June and August, they have a 9 AM departure with Odyssey Whale Watch, and this is the perfect time of year to see the migrating humpback whales.

If you haven’t spent much time out on the ocean or it’s your first whale watch, I’d recommend taking some motion sickness tablets beforehand. It’s an amazing experience to see these creatures up close!

Chances are you’ll also see seals, dolphins, various birds, and marine life.

If you opt instead to go during the fall for the foliage, you can instead do their lovely lighthouse tour.

Artemisia Café

When you get back to land, head to Artemisia Café for lunch, it’s a neighborhood spot right in the arts district, and they serve up delicious foods in a fun atmosphere.

Peak’s Island

Once you’ve had your fill take a ferry over to Peak’s Island. Here, you can take in the small-town vibes and natural beauty of Maine’s coastline. The ferry is a short 15-minute ride. Once on the island, enjoy its quaint and low-key atmosphere.

The island became a trendy summer destination for Maine residents in the 1800s and was at the time known as the “Coney Island of Maine.” The island is perfect for beaches, water activities, relaxing, and a bit of local history and exploring. 

Both Sandy Beach and Centennial Beach walk from the ferry and are great spots to walk to enjoy.

The Inn on Peak’s Island is perfect for a scenic meal at the end of your day before taking the ferry back to the mainland. If you want to extend your stay, they also have classic Maine cottage-style accommodations available as well.

3 days in Portland is not a lot but will allow you to see the most beautiful places and have a fun trip. Hopefully, this Portland itinerary will help you plan your time in Maine, and you can discover the best in a short time.




Cassandra is a US-female travel addict who loves traveling the world and a freelance writer at ArzoTravels. She has made traveling her priority, and so she has traveled for the last few years. She has also become a regular contributor to this website – Arzo Travels.

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