Best Things to Do in Portland in 3 Days – an Itinerary
- 1 Best Things to Do in Portland in 3 Days – an Itinerary
- 1.1 Portland Travel Tips
- 1.2 Day 1 in Portland
- 1.3 Day 2 in Portland
- 1.4 Day 3 in Portland
This post was written by Cassandra
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!
Portland, Maine, is a lovely historic harbor filled with New England Charm. It’s the perfect addition into an east coast road trip, 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 as well as nearby skiing resorts the options are endless.
Portland Travel Tips
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 point of northeast US as well as train from other major east coast cities.
How to get around
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 is also available.
Best Time to Visit
Summer or Fall. Unless you are looking to partake in winter sports like skiing or snowboarding than it’s best to avoid the harsh winters here. 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 their gorgeous colorful autumn foliage.
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 Maine 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 and keep any valuables or bigger sums of money out of sight.
Like most cities in the US Portland Maine can be pricey but still much more affordable than its larger counterparts like NYC.
Average entrees would fall around $15 USD 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 more around $20 per person.
Portland Maine is a foodies paradise, brimming with breweries, wine bars, cafes and a wide variety of restaurants- many being farm to 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.
Day 1 in Portland
The first day is perfect for just exploring leisurely by 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 bakery classics, I recommend the cinnamon buns!
Portland Museum of Art
From here 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.
Portland is a city filed with artists and art schools so it’s a great spot to enjoy museums and galleries!
After having your fill at the museum take a self-guided tour of the Freedom Trail.
This is a famous historical trail in the American abolitionist movement be sure to download or print out the map offline beforehand.
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.
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.
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 started as a wine shop and bar to showcase natural wines and evolved to include an amazing restaurant that creates meals that can be perfectly paired to the wines, it’s the ideal stop for a delicious meal and some wine to end to the day.
Day 2 in Portland
Start your morning with a hearty breakfast at Becky’s Diner.
Becky’s is a traditional American dinner in the waterfront that opened in the 1990’s, it’s a charming family run business serving up all the classics and definitely worth a stop during your stay!
From here head to the Victoria Mansion, it’s an absolutely gorgeous Portland landmark and only a short walk from the diner.
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 1800’s and was saved and opened to the public in the 1940’s it’s currently open 10 AM -3:45 PM daily and it’s a unique sight in Portland
Great there at opening so you can enjoy it without crowds.
Old Port District
Afterwards head to the Old Port district and join the Portland Craft Drink tour!
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 can 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 there is another that runs at 2:30 PM.
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.
Portland Paddles Kayak
From here you can join one of Portland Paddles kayaking tours. They have a few tour options as well as 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 water side you’ll have worked up an appetite!
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 time to experience the overwhelming natural beauty of Maine!
Odyssey Whale Watch
Start with a morning whale watch. Between late June-late 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 and various birds and marine life.
If you opt instead to go during the fall for the foliage you can instead do their lighthouse tour which is lovely.
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.
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 coast line. The ferry is a short 15-minute ride, once on the island simply enjoy it’s quaint and low-key atmosphere.
The island became a very popular summer destination for Maine residents in the 1800’s 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 are walking distance from the ferry and great spots to walk to enjoy.
The Inn on Peak’s Island is perfect for a scenic meal at the end of you day before taking the ferry back to the mainland, if you wanted to extend your stay they also have classic Maine cottage style accommodations available as well.
READ MORE: FUN CITIES TO VISIT IN THE US
ABOUT THE AUTHOR
Cassandra is a US-female travel addict that loves traveling the world and freelance writer at ArzoTravels. She has made traveling her priority and so she has traveled for the last few years. Check out her site where she sells her travel photography. She has also become a regular contributor for this website – Arzo Travels.