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Discover Portland, Maine: A Complete Itinerary For Every Traveler

Portland, Maine might just be one of my favorite little cities in New England. It’s got a little of everything I love – nice locals, good food, pretty scenery, and a neat history, too. I mean, who doesn’t love the look of whimsical 18th century buildings on brick lined streets? Whether you are staying one day or a few nights in Portland, I’ve created the perfect Portland, Maine itinerary to help you make the most of your trip. Because Portland has so much to offer.

So no matter if you’re into the outdoors, consider yourself a foodie, or perhaps love a good local history – you’ll find something in this itinerary perfect for you. And with a local-first approach you might find a few hidden gems, too. Because this small city has big-city feels you’ll love. Because the Pine Tree State has a lot to offer!

Happy travels to Maine!

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A Quick Guide to Portland, maine

🏨 Places to Stay
The Westin Portland Harborview (my top choice!)
The Francis Hotel
The Chadwick Bed and Breakfast

🍽️ Places to Eat
Standard Baking Co.
Eventide Oyster Co.
Becky’s Diner

👩‍🎨 Things to Do
Book a food tour
Bike the coastline
Stroll the Old Port

Where to Stay in Portland

Portland, Maine might be the sweetest town but it isn’t the cheapest to stay in, especially during high season (June-August) where hotel prices can easily rise to over $300 a night.

Hotels in downtown within walking distance to shops and restaurants are the most expensive. If you can’t find a hotel that fits your budget consider staying in Kennebunkport instead. It’s a smaller coastal town less than 30 miles from Portland.

If you are wanting to stay in Portland here are a few hotel suggestions based on your budget:

Hotels on a budget (<$150 a night)

The Westin Portland Harborview
Cambria Hotel Portland Downtown Old Port

Want to save more on your hotel? Hotels near the Portland Airport are the cheapest option but a bit outside the main city center. Many of these hotels are also available with points, which means you could be paying nothing for your nightly rate!

>> Learn more about how to earn a free hotel night to help you save on your Portland hotel (and many more after that)!

Mid-Tier hotels (<$250 a night)

The Francis Hotel
The Chadwick Bed and Breakfast

Splurge and stay here (>$250 a night)

Blind Tiger Portland

How many days should I spend in Portland, Maine?

Many people opt for a single night or even day trip when visiting Portland. But you can easily find enough to do for 3-5 days in the small coastal city. Typically 1-2 days is what travelers choose when visiting Portland.

When to visit

Personally I think the best time of year to visit Maine is shoulder season, which runs mid-April to Memorial Day and again September to October. Spring sees the lowest prices for hotels, which can save you hundreds on your accommodations.

If you can, I’d recommend visiting late-April. You’ll have great weather, all the season activities and restaurants will be open, and you’ll pay less with far fewer tourists.

Things to see in Portland Maine

Take a boat tour

One of the best ways to experience Portland is on the water. My boat tour was one of my favorite things I did! You learn a lot about the fishing industry (hello, lobster and oysters) and see some of the New England sea life on a boat tour, too. Booking a tour in advance will ensure you get a spot on a boat but you can book in-person right before a boat leaves, if there is space available.

Visit the Portland Museum of Art

Come see the collection at the oldest art museum in Maine. The Portland Museum of Art is a great way to spend a rainy afternoon or early morning in the city. They have a wonderful collection for its size, especially in the American and Impressionist collections. And as a bonus the museum is free every Friday from 12 p.m. to 8 p.m.

Travel Tip! Do you have a membership to your local museum? You might have what's called a reciprocal membership to the Portland Museum of Art! This gives you free admission - just be sure to bring your membership card to the museum you are a member.

take in the views at the Portland Observatory

What was once a communication station in 1807 for the bustling ship harbor is now a unique destination in Portland. Now the observatory gives amazing views of the surrounding city and seaside to visitors. Keep in mind the observatory keeps some strange hours, so be sure to check here before heading over to snag a guided or self-guided tour.

Have a beer at some of the best New England breweries

New England brewery culture can’t be missed on a trip to Portland. You can find dozens of great breweries in Portland and the surrounding areas but some of the best are Allagash Brewing Company and Belleflower Brewing Company. (I also liked Rising Tide and Austin Street!)

>> If you want to do something a little different consider a guided brewery tour of the Old Port.

Shop local

If you like finding unique local products Downtown Portland has plenty of places to find them. One that I always recommend is Sherman’s, Maine’s oldest bookstore. Sherman’s has locations in a few Maine cities (I love the little one in Bar Harbor) but either way supporting this continuing local bookstore is worth the visit.

Some other local shops to add to your list:

Stroll the Old Port

There is nothing more New England than strolling 19th century brick buildings near the fishing docks. Still a working port you’ll find lobster traps, fishing boats, and so much more near the Old Port in Portland. Nowadays the port is full of unique restaurants and shops to wander through.

>> If you want to learn more about Maine’s history you can book this walking tour, which includes the Old Port!

Take a drive to the Portland Head Light

Located 5 miles from downtown the Portland Head Light is a seaside lighthouse completed in 1791. The lighthouse is in the Fort Williams Park. The park is a nice place for a walk, too.

I recommend bringing your morning coffee and pastry from Standard Baking Company out to the lighthouse in the morning. It’s the perfect way to relax with the waves crashing into the rocky shoreline.

Take the ferry to Peaks Island

If you want something local to do try taking the public ferry to Peaks Island for a day trip. Tickets are $14 with a variety of departure times you can choose from. Ferries are operated by Casco Bay Lines which operates passenger and car ferries in Maine.

If you only have a day in Portland I’d probably skip a trip to Peaks Island but if you’re staying a few days and want a slower pace, local activity it’s a great option.

Bike the coastline

See a different side to Portland with a guided bike tour around the coastline. Portland is very flat and easy to ride, making it a great way to spend a sunny day. If you’d rather bike yourself you can DIY a similar experience renting a bike in town, too.

Visit the Victoria Mansion

With construction of the mansion completed in 1860, the Victoria Mansion was a summer home for a wealthy New Orleans hotel mogul. The home is a great example of the Italian Villa style with guided tours. The mansion is well preserved, showcasing 19th century lift in Portland.

More things to do in Portland, Maine

What to eat and drink in portland, maine

Portland is a foodie paradise with plenty of amazing places to eat and drink throughout the city. The longer you visit the more you can give deep into the rich culinary universe that is Portland but with just a couple of days the highlights will still be exciting.

If you only have a day or two in Portland I recommend checking out a food tour. Joining a food tour will make sure you get to try all the Maine classics, like lobster rolls and oysters.

Best places to get a coffee

Where to get a lobster roll

Get a drink at these spots

Have a meal on a budget

Portland Maine Itinerary: A Quick Guide

One Day in Portland Maine

Start your morning with a trip to Standard Baking Co. Grab a morning bun and coffee from this fan-favorite. Their morning bun is one of the best I’ve ever had and at just $4 it’s a steal, too. Keep in mind this is a local and visitor favorite so you might be waiting in a line out the door. Don’t worry – the line moves fast and is so worth it.

Afterwards spend your morning on a guided bike tour around the peninsula. You’ll get to see a lot of the amazing coastline, including lighthouses and 19th century homes. If bike tours aren’t your thing instead try a culinary walking tour to try all the amazing foods Portland has to offer. Either way you’ll get to see a lot of the city and get some recommendations from your guide along the way, too!

After your morning tour take to the local shops that line the Old Port and beyond. If you like to read be sure to stop at Sherman’s, the oldest operating bookstore in Maine. It’s one of my favorites! Or, if you’re looking for something as a gift (or a souvenir from your trip) take the time to visit The Maine Souvenir Shop. They have over 100 artists works from home goods to clothing and a lot more.

From the Old Port, stop at Belleflower Brewing Company, which has a great selection of beers. It’s certainly a local spot just outside the old town. You can try New England style beers but they also have IPAs, sours, and other beer styles, too.

Make a dinner reservation at Eventide Oyster Co. and enjoy a dozen oysters to start. You can ask for a sampler to try a variety of local oysters – many raised and harvested within 30 miles from the restaurant! Afterwards order to lobster roll, which is served on a steamed Asian bun. It’s delicious and unique.

Depending on the season you can join a sunset sail on a Windjammer. Be sure to check the seasonal operating times and plan your evening accordingly.

2-Days in Portland

If you have a few days, start your next morning at Holy Donut. Known for their potato donuts, they have a flavor for everyone. But if you want something a bit more substantial try a breakfast sandwich at Artemisia Cafe.

After breakfast take a trip on the water with a morning lighthouse cruise (if you haven’t been on the water yet it’s a must!). Or, consider a guided walking tour of the historic district.

Be sure to stop at Luke’s Lobster and snag a lobster roll before you leave Portland. It’s a must and a great place to enjoy the views of the fjords, too.

This afternoon enjoy one of the many museums in Portland. The Portland Museum of Art has a great collection of art and is free to visit on Fridays after noon. But if you like history consider visiting the Maine Historical Society to learn. more about Maine’s long and unique history.

For dinner consider going big at Central Provisions, an upscale menu with unique, complex flavors. But if you’re on a budget try Becky’s Diner, a no-frills eatery with amazing clam chowder. Be sure after dinner to snag a drink at Blyth and Burrows cocktail bar.

The Portland Observatory closes at 8:00 PM on weekdays, so be sure to head up and catch one last glimpse of the amazing Portland skyline from the historic building.

Have more time in Portland? Take a day trip!

After two days in Portland you might want to venture outside of the historic town. There are plenty of great day trips near Portland, Maine worth checking out. Here are a few of my favorites:

Freeport

Located 17 miles north of Portland, Freeport is a great day trip. Freeport is home to the LL Bean Outlet Store but it has a lot more to offer, too! Wolfe’s Neck Woods State Park is beautiful and a great way to get outdoors in one of the best states to do so.

Kennebunkport

Located less than 30 miles from Portland, Kennebunkport is a sleepier small town with a beautiful old town and beaches. Dock Square has some great restaurants and small shops to stroll through and walking the shoreline of Goose Rocks Beach is the perfect way to spend a sunset.

Bath

Located 35 miles from Portland, Bath is known for its incredible downtown area but be sure to check out the Maritime Museum. Here you can learn about the long shipbuilding and waterway history that made Maine, well, Maine.

FAQs

What is the best month to visit Portland, Maine?

Spring to fall are great times to visit Portland. You’ll get the best prices on hotels, good weather, and all the season activities and restaurants back open for business.

Are two days enough in Portland?

Two days are enough to see the major sites of Portland and take a few guided tours, too. If you need to spend less time in Portland you can make a day trip work, too!

How do I get to Portland, Maine?

You can fly directly into Portland International Jetport or fly into Boston and drive about an hour and 45 minutes to Portland. Typically flights into Boston are cheaper but if you otherwise wouldn’t rent a car flying into Portland might be the cheaper option.

More Maine Tips and Inspiration

I hope you found this Portland Maine itinerary helpful for your trip! I love Maine and Portland is just the best little coastal town. If you liked this itinerary be sure to check out some other Maine travel inspiration.

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