Portland Maine Itinerary | Perfect For A Few Days

Maine has a favorable reputation of being a wonderful place to visit. This tucked away New England state has become even more popular in recent years and really is a great place to vacation. My sister and friend came to see us while in Portland making it even more special. We had a few days packed full of activities from shopping, exploring, eating, drinking, tours and time on the water. So if your looking for ideas on the perfect Portland Maine Itinerary, we have lots of ideas for you!

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What to expect from Portland Maine

Portland is Maine’s largest city, and it was the first stop on our tour of Maine. (Our Maine stops include Portland, Freeport, Boothbay, Camden, Belfast, Acadia and Bar Harbor). 

Downtown Portland Maine

Portland is actually a peninsula with water views on three sides from Old Port to West End and East End. It is a city without tall building (no more than 175 feet) and no billboards. This is a Maine state rule to preserve the beauty and protect the views. Therefore maintaining Portland’s small town feel even though its Maines largest city.

The city offers many things to do. You can choose from a variety of indoor activities such as great restaurants, coffee shops, best breweries, historic buildings, art galleries and museums. Or try some outdoor activities such as relaxing on sandy beaches, enjoying a scenic drive, exploring walking trails or being on the water.  

Portland Maine has activities for everyone. So after we spent a week exploring downtown Portland and the surrounding area, these are my recommendations. So, here you’ll find the best places to add to your Portland Maine itinerary.

Where is Portland, Maine

Portland is located in lower Maine on the Atlantic coast. Maine borders New Hampshire and specifically Portsmouth along the east coast.

If you’re driving into Portland, the nearest highways are I95 and I295. These are the driving distances from nearby cities: 

  • from Boston MA 107 miles 
  • from Montreal Canada 256 miles
  • from Manchester NH 95 miles
  • from Bar Harbor ME 175 miles

If you plan to fly into Maine, then you have a few options. You can fly into Portland International Jetport, Manchester NH, or Boston MA. Sometimes you can find better deals by flying into MA or NH and driving in. 

Having a car in downtown Portland is not necessary, however if you want to explore beyond that, I would recommend a car.  

Best time to visit Portland

Maine has four seasons: June, July, August and winter. Well, that’s what we were told on our trolly tour. But all joking aside, Maine winters are cold. So the best time to visit is between late spring and early fall. 

Water view from Old Port District in Portland Maine

Summer months have the best weather but also the most crowds.

After Labor Day in September and October are considered shoulder season and temperatures are still pleasant with less crowds. 

Anytime during these months, should be a nice visit. So with that being said, lets talk about the best things to do for a Portland Maine Itinerary.

Ideas for a Portland Maine Itinerary 

1. Make a stop in Kennbunkport 

If you are driving into Portland, then you have to make a stop at Kennebunkport along the way. This cute coastal town is how you image small towns in Maine must look: waterfront, historic, charming with fresh seafood everywhere! And Kennebunkport is no exception.

Afternoon in Kennebunkport. Dining on the deck at The Boathouse Restaurant

Our group only had a few hours in Kennebunkport, and could have definitely spent more time. We walked around the shops and had a delicious dinner. We ate at The Boathouse Restaurant where we sat outside with waterfront views.

Kennebunkport is a great option to experience small town Maine.

Did you know Walker’s Point Estate (or the Bush compound) is the summer home of the Bush family, in the town of Kennebunkport, Maine. So, yes, its a nice place!  

2. Visit the Old Port District

If you like shopping, historic buildings, craft beer, delicious food and especially lobster rolls, then you will love Portland. It’s a fun city!

Geographically the Old Port District is bordered by Franklin Street (U.S. Route 1A) to the east, Commercial Street to the southwest by the water, and 19th-century buildings to the north.

The Old Port is also surrounded by the neighborhoods of Bayside, East Bayside, Munjoy Hill and the West End. However most of the action in Old Port is on Commercial Street, Fore Street, Exchange Street and at night, Wharf Street. 

Below are all great ideas in within Old Port to add to your Portland Maine itinerary:

Explore local shops and art galleries 

Did I say shopping? There are so many great shops in Portland. So if you like to shop, you found your spot other than driving to Freeport.

Old Port District of Portland Maine Itinerary

Explore Portland’s boutiques and specialty stores for one-of-a-kind finds, including handmade crafts, vintage items, all things lobster, whoopie pies and more.

You will also find numerous art galleries and pottery stores. 

I purchased some red lobster lollipops for my sister to take back to my nephews. They loved them!

Indulge in a potato donut at Holy Donut

We always like to find tasty treats in new places. So when I heard about Holy Donuts and their potato donut, well I knew we had to give it a try. It definitely has a different texture from regular donuts.

Donut selection at Holy Donut

In my opinion, the potato makes the donut more dense and therefore more filling. The donuts are big in size and I recommend getting one with a flavorful frosting. If you like unique sweet treats, give it a try!

They also have vegan and gluten free options.

photo opp outside the Holy Donut

Donut Tours are also available in the city. So if you want to learn more about donuts and visit other donut shops around Portland, you might consider one.

Dine on delicious fresh seafood

The food scene in Portland is really good. There are many well rated restaurants in the downtown area. Almost too many to mention.

I will say this, if you have a place you really want to eat at, then make a reservation in advance. With our group of 4 the wait time at the best restaurants like Central Provisions was over an hour. 

The city is full of great options for a lobster roll, clam chowder, fresh oysters and other ocean-inspired dishes.  

A really fun place for lobster rolls or lobster on a stick is The Highroller Lobster Co. This diner style restaurant started off as a food truck and has continued to grow and expand ever since! 

Maine Lobster Roll

Culinary Tours are also a popular option to experience what the city has to offer from seafood, cheese and more.

And if at the end of your trip you can’t eat any more lobster and you just want some pizza. Give Pizzaiola a try. After our sunset trailing trip, we all had a slice, and it totally hit the spot!

Drink craft beer from local breweries

Portland is a hub for craft beer. It has the more craft breweries than any other US city. So for all the beers fans out there, get ready to do some tasting. 

Beer flight at Shipyard Brewery Company

There are many local breweries just a short walk from each other in downtown Portland. Offering a variety of beer selections such as pale ales, fruit beers, sours, belgian-style beers and many others.

Here are some popular ones to visit, but its just a short list, as there are many more!

  • Shipyard Brewery Company 
  • Allagash brewing Company
  • Bissell Brothers Brewing Company
  • Sea Dog Brewing Company

We enjoyed a great beer flight at Shipyard Brewery Company and loved Portland Mash TUN on Wharf Street for a cool vibe tavern offering a variety of local craft beer. 

You an also opt for a guided brewery tour.

There are many ways to taste your way through Portland!

Walk down historic Wharf Street 

Wharf Street comes to life at night. This cutest of cobblestone streets is a narrow, almost alley way street. It is pedestrian only during the summer months, that way you don’t have to worry about cars when its busy.

Cobblestone Streets in Old Port

This street represents Portland’s rich history and lively present. So even if you’re not dining along the street, you should at least walk down it. That way you can experience some of the history and the ambiance of this high energy street.

PARKING TIP: Parking in Portland is both expensive and can be hard to find. We found two affordable lots, so if you’ll be spending more than 4 hours in town, they are worth it. 

  • One lot is only $5 for the day, with a little further to walk at 450 Commercial Street  
  • The other lot is $20 for the entire day located near the pier at 2 Commercial Street

Take a trolly tour around town 

This was our first time in Portland, so we were unfamiliar with the city layout and neighborhoods. Therefore we decided to take a trolly tour to get acquainted with the city.

Trolly Tour start and finish location in Old Port

The trolly tour has two options: Tour with Lighthouse or Tour without the Lighthouse. So, if you plan to visit the lighthouse on your own, then opt for the NO lighthouse tour. 

On the Portland Trolly Tour

On the trolly, you will see many areas of the peninsula. It gives you a nice overview of the city and then you can decide if you want to come back and experience more. Here are some highlights of things you will see and can do later:

Walk the Eastern Promenade

With beautiful views of Casco Bay, this is the perfect place to enjoy outdoor activities. You can walk or bike along the 2.1 mile Eastern Promenade trail that connects to downtown.

Views of Casco Bay

At the park you can plan a picnic, enjoy East End Beach or just relax and take in the scenic views. Its a beautiful 68-acre historic landscape, worth a visit. The perfect place for a morning walk or afternoon stroll. 

Visit the Portland Art Museum

For the artists at heart, immerse yourself in art at the Portland Museum of Art located in the Arts District of downtown Portland.  

Known for being the oldest and largest art institution in Maine, the museum features an impressive collection of American, European, and contemporary works.

It is closed Monday and Tuesday although open throughout the year.  

Tour the Victoria Mansion 

Tour the lavish Victoria Mansion, a National Historic Landmark that showcases stunning architecture and interior design from the mid-1800s. The mission is to conserve, maintain and restore, as the house still has over 90% of the objects that were in the house in 1860.

Tickets available from May 1 to October 31 with advance tickets recommended.

Climb the Portland Observatory 

For panoramic views of the city and the harbor, climb to the top of the Portland Observatory, a historic maritime signal tower.

Portland Observatory | photo credit portlandlandmarks.org

So, if you would like to see a birds eye view of the city, you should plan to visit. 

Open seasonally with guided tours offered Thursday to Monday and self-guided tours on Saturday.

As you can see, the Old Port District is full of fun things to do. However, if your looking for a more quintessential Maine small town feel, then you may want to consider adding smaller cities into your travels too. 

Portland Maine Itinerary outside of Old Port District

4. Enjoy beautiful views of the Portland Head Light 

Just a few miles from downtown, in Cape Elizabeth is the Portland Head Lighthouse. This iconic lighthouse one of the oldest lighthouses and also one of the most photographed lighthouses in the United States and for good reason. 

Visit the Portland Head Lighthouse as part of your Portland Maine Itinerary

With breathtaking ocean views, historic surroundings and scenic walking trails the park is both beautiful and peaceful.  Because the park is so nicely landscaped, you really just want to hang out and enjoy it all day. We walked the cliffside path and enjoyed views of the lighthouse from both directions. 

On the cliff walk at the Portland Head Light

With 90 acres of space, Fort Williams Park is the perfect place to spend an afternoon. And being an outdoor and nature lover, this was one of my favorite things to do. 

The park is free to visit, you only pay for parking and a small fee to tour the museum. Food trucks are also onsite if you need lunch or a snack. 

There are 5 other lighthouses nearby to visit including Bug Light Park and Spring Point Ledge Lighthouse. 

5. Spend time on the water

Downtown Portland is located on the water. And that means there are lots of options when it comes to water activities. So whether you want to learn about lobsters, search for whales, relax on the water or head over to a nearby island, there is an activity waiting for you. 

So for your Portland Maine itinerary, make sure to include some time on the water.

Lucky Catch Cruises

If you like lobster and looking for a totally Maine experience, then check out Lucky Catch Cruises. This 1.5 hour lobster tour cruises the harbor while you get a hands on lobster fishing experience. And as you can see they go out rain or shine! Unfortunately Scott and I had to postpone our tour and got the rain.

Rain or Shine on Lucky Catch Cruises

At the end of the tour, you will know how to trap lobster, be able to determine the sex, learn how they protect against overfishing, and purchase a fresh lobster for lunch or dinner.

Fresh Lobster dinner cooked right off the boat at Portland Lobster Co.

The experience was more informative rather than adventurous, however, we really enjoyed it.

Whale Watching Tour 

There is something magical about whale watching. And if you’ll never experience it, you definitely should. 

In Maine, whale watching season is mid April thru October. So if you visit during these months, You will have the opportunity to see humpback, finback, mine and pilot whales. Try to pick a clear sky day, because Maine’s fog will take away your visibility to spot the animals. 

The Odyssey Whale Watch Tour is 4 hours and they go out about 15 miles looking for whales. While there is never a guarantee for seeing whales, it is highly likely to spot a few in season.

Sail the harbor in a Schooner

Another great way to get on the water is a 2 hour Windjammer cruise. Sail around the Casco Bay and enjoy the views of picturesque lighthouses, the rugged Maine coastline line, spot a harbor seal and just relax. 

Aboard the Portland Schooner in the Casco Bay

We went on the Portland Schooner sunset sail and even though it was cloudy and lacked a sunset, the sail was very relaxing and enjoyable. Its BYOB, so you can enjoy a beverage while sailing around.

It was a great evening on the water sipping wine with friends and family. 

Take the ferry to Peaks Island 

Maine has so many small islands off the coast. So, if you’re curious about them, take the Casco Bay Ferry and explore the nearby Casco Bay Islands. 

Peak Island is the most populated and makes a fun day trip. On the island you can bike, hike and enjoy the stunning coastal landscapes. We didn’t get a chance to visit. However, we did get a peek from the water on our schooner sail. 

Kayak the salt marshes 

We stayed just outside of Portland in Scarborough. Nearby our campground was Scarborough Marsh Audubon Center. Little did we know, this is the largest salt marsh in the state. We rented a kayak and spent about 2 hours on the water paddling out and back. It was fun, even though we got caught in the rain. 

Kayaking the salt marshes

Maine’s tidal elevation change is around 8 feet or more. So, make sure you watch the tide chart because at low tide, there is not enough water to paddle through.

6. Day trips for your Portland Maine itinerary

Want to experience Maine outside of its largest city? Consider a little day trip outside of the Portland area. These are some other places we visited:


The small town of Freeport is less than an hour away. With a plethora of outlet stores, this small town is also home to the LL Bean flagship store.

LL Bean has a great story and continues to offer exceptional service to its customers. As the stores are open 24 hours a day. That’s right, they never close. So if you feel like late night shopping, its available. 

Boothbay Harbor

Just a little over an hour away, this Mid-Maine coastal town is small and charming with a harbor side downtown. Boothbay is another classic seaside Maine town with a chill coastal vibe, fresh local seafood and quintessential clambakes.

Coastal Maine Botanical Gardens


Another really cute coastal town is Camden. It is a place where the mountains meet the sea, with a charming downtown, historic architecture and scenic mountain hilltop views.  

Top of Mt Battie at Camden Hills State Park

Acadia National Park 

While not recommended as a day trip, it is as a side trip. Acadia National Park is by far the most popular national park in Maine. And a great place to visit.

However, if visiting another small city is not on your agenda. You can still explore outside of Portland by visiting a blueberry farm, apple orchard, maple sugar house or even a vineyard. 

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In Conclusion

As you can see, the Portland area has so many fun things to do! From a day trip, long weekend or week long stay. Portland is full of activities from land, sea and sport. 

So whether Portland is your final destination or part of your road trip, this Portland Maine itinerary will help you discover the best parts of town.

Enjoy and have fun on your Portland adventure!

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