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Explore the Portland Old Port with a Culinary Walking Tour

Explore the Portland Old Port with a Culinary Walking Tour

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Looking for awesome tours and sightseeing in Portland, Maine? This Portland, Maine, food tour is one of the top things to do in Old Port, Maine, for foodies!
This post about culinary experiences in Portland, Maine, was written by family travel expert Marcie Cheung and contains affiliate links, which means if you purchase something from one of my affiliate links, I may earn a small commission that goes back into maintaining this blog.

One of the best ways to explore a city is through its cuisine. That’s why I booked a Portland Old Port Culinary Walking Tour through Viator on my recent trip to Portland, Maine, for the Women in Travel Summit.

I had heard great things about these Portland, Maine, food tours and had to try them out for myself!

Portland Old Port

Maine Foodie Tours offers all kinds of Maine walking tours, mostly in downtown Portland (like their new “Bon Appetite” Culinary Walking Tour, Fun-Filled Progressive Dinners, Tastes of the Top: A Restaurant Tour, Old Port Lunchtime Lobster Crawl, India Street Food Artisans, and The Culinary Palette: Art, Culture, and Food Tour.)

However, I chose to do their Old Port Culinary Walking Tour in downtown Portland.

Portland’s Old Port is a historic neighborhood right on the waterfront. Here, you can find boutique shopping and tasty restaurants, as well as a real working waterfront with fishing and cruise boats.

As you walk on the cobblestones (well, technically, they are pavers), you’ll feel instantly transported back in time.

Something you’ll notice about Portland Old Port is that you won’t find a lot of chain restaurants or stores. There are a few, but the vast majority are independently owned and operated.

And I have to talk about the architecture! It’s really stunning! So much of Old Port Maine tourism involves historic buildings.

As you walk around town, you’ll see Portland’s City Hall, which was built by the same people who designed the New York Public Library.

You’ll also see how the city changed after the big fire of 1866 when some kids lit fireworks and ended up torching all of Portland. Darn, kids!

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Explore the Portland Old Port with a Culinary Walking Tour

Maine Foodie Tours: a Portland Old Port Culinary Walking Tour

I walked down to the meeting spot at Old Port Wine Shop about 15 minutes early and was surprised to see the rest of the guests also got there early!

I guess we were all hungry!

Maine Foodie Tours meets at Old Port Wine Shop in Portland Old Port.
After I put on my badge, I was ready to eat my way through Portland Old Port! Photo credit: Marcie Cheung

We met our tour guide, Chuck, who enthusiastically told us all about Portland Old Port and what we could expect on the tour of Old Port Maine restaurants.

He did an awesome job of introducing everyone on the tour and we instantly started chatting away.

Since I attended the tour on my own, I really appreciated being included from the get-go and not feeling isolated.

After introductions were out of the way, it was time to start the tour!

Note: The stops on the tour change from time to time.


Chuck actually brought our first stop to us! On his way to Old Port Wine Shop, he grabbed a box of donuts from the infamous The Holy Donut.

The Holey Donut is one of the top bakeries in Portland Old Port, and they are known for using potato flour to make their gourmet donuts.
The Holy Donut is the trendiest donut shop in Portland, Maine. Photo credit: Marcie Cheung

I hadn’t heard about them until I started researching places to eat in Portland, Maine, and they kept coming up.

They are the trendiest donut shop in Portland, and lines are usually out the door!

What sets them apart is that they are made with potato flour. They are super light and fluffy, and the flavors come through well.

He brought fresh lemon (there was even lemon zest!) and sea salt chocolate (one of their most popular flavors!)

Chuck cut them in half, so we got to try half of each flavor. OMG, they were tasty!

I almost went back on my last day so I could bring them home, but I wasn’t sure they’d make the flight home!

Insider tip: Bring a container so you take a few bites and save the rest for later. You won’t want to fill up on donuts at the start of the tour!


This was actually my first tour of Portland Old Port, so it was nice to do it on foot. Part of that is because when we talked about the paver stones, I could reach down and take a closer look.

Portland Old Port is full of cobblestone streets made with pavers.
One of the many cobblestone streets in Portland, Maine. Photo credit: Marcie Cheung

USA Today Travel Experience America actually rated Portland, Maine’s Wharf Street as one of the ten prettiest cobblestone streets in America.

When you stroll down it, you’ll understand why!

We also stopped at the Maine Lobsterman public art piece designed to represent Maine in the 1939 New York World’s Fair.

There, Chuck talked to us about the vital role of fishing in Maine’s economy.

Then, we walked past the Farmer’s Market, which locals claim to be the longest-running farmer’s market in America!

The Farmer’s Market is located in Monument Square. That’s where you’ll find the statue of Our Lady of Victories.

It’s in honor of the 5,000 Portland soldiers who died in the Civil War, fully one-sixth of its population.

Throughout the years, Monument Square has been the location of many protests, including ones focused on prohibition.

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Coming from Seattle, I’m a huge connoisseur of seafood. We have some amazingly fresh sushi and I was very curious what sushi was like in Portland, Maine.

Mr. Tuna is one of the best sushi restaurants in Portland Maine and you'll find it in Portland Old Port near Monument Square.
I’m still thinking about how tasty this crab hand roll was! Photo credit: Marcie Cheung

Chuck took us to Mr. Tuna, one of the top sushi restaurants in Portland, Maine. There, we tried their crab hand-rolled sushi, also known as a sushi burrito.

This was the perfect size to try!

The nori (seaweed) was crispy and the crab had the perfect blend of mayo with just enough veggie for a crunch.

Mr. Tuna used to be a food cart. Then, they upgraded to a food truck.

Now, it’s a full brick and mortar inside the Public Market House, a cool place filled with delicious food options and lots of seating.

The whole place had an eclectic vibe. And I heard that upstairs they have even more ethnic foods and shops.


Next up was Scattoloni Bakery, not too far away near a bookshop.

They offered us some water (we were all so thirsty!) and gave us the option of trying their minestrone or creamy tomato bisque.

Scattoloni Bakery is known for their gourmet soups, breads, and bakery in Portland Old Port near Monument Square in Portland, Maine.
This was the best vegan tomato bisque I’ve ever had! Photo credit: Marcie Cheung

I chose the tomato bisque, as did the majority of the group.

The soup was served with homemade focaccia bread. The focaccia was doughy in the best way possible and was incredible on its own or dipped in the soup.

While we ate, Chuck showed us sketches of the Portland Observatory, a historic landmark that was used to tell the community what ships were coming into harbor.

As we left, we each got to pick a cookie or bar to take home. They wrapped it up, and we were on our way!

Find out where to eat in Portland beyond these places.

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I really couldn’t get enough of Portland, Maine’s fascinating history, so I was glad we got to learn a bit more as we worked up an appetite.

The Colesworthy building in Portland Old Port has a real cannon ball on the exterior!
Yep, that’s a cannonball decoratively placed in that building! Photo credit: Marcie Cheung

One of my favorite spots was the Colesworthy building. The builder decided it would be interesting to decorate the exterior with a real English cannonball.

It’s one of the things I probably wouldn’t have noticed had I walked around by myself.

We also heard the story about the huge Portland fire of 1866. It was started by 2 kids playing with firecrackers, and by the end, 13,000 people were homeless.

Thankfully, no one died.

However, that’s the reason so many buildings have distinctly different looks, especially from the bottom to the top.


I’m all about smoothies when we travel. I find it hard to get enough fruits and vegetables at restaurants, and so I feel better when I get some fresh juice or a smoothie.

Blake Orchard is one of the best juice spots in Portland Old Port.
Just look for the lovely blue building, and you’ll know you’re at Blake Orchard!

Blake Orchard a very small place inside, but they have gorgeous pink wallpaper just screaming to be posted on Instagram! It’s my featured photo in this blog post!

We got to try a half serving of their Sweet Ginger smoothie made with: house-made almond milk, banana, pineapple, maca, almond butter, date, ginger, and garnished with chopped almonds.

I’ve never had that combo before, but it was so tasty! Not too sweet, but definitely flavorful!

They are opening up a second location soon.


Just as I thought it was odd we hadn’t tried Portland’s most famous dish (the lobster roll), we walked inside Gritty’s.

What's a trip to Portland Old Port without lobster rolls? Gritty's has some of the best lobster rolls in Portland, Maine!
Gritty’s is home to one of the best lobster rolls in Maine! Photo credit: Marcie Cheung

This is one of the most famous restaurants in Old Port, Maine, because of its lobster rolls and beer selection.

This was definitely the biggest meal of this Maine foodie tour, and it was fantastic.

We started by getting to try two different ales: one dark and one light. I’m not a beer/ale drinker, so I’m not the best judge. I will say the light one tasted pretty good with the lobster roll, though.

Under Gritty’s is where they make the beer, which goes directly to the tap in the bar.

There’s a mural on the wall depicting the entire process (although the naked people on the mural are not part of the process!)

After learning about the ale process, our food was ready!

We each got half a lobster roll and a generous portion of fries. The lobster roll was on a nice, buttery roll, and the lobster was mixed with mayonnaise.

While we ate, we learned about soft lobster and why they can’t ship it. Apparently, that’s what Mainers like to eat, and I’m hoping to visit during the soft lobster season!


This Maine Foodie Tour ended the way it should: with chocolate!

These lobster lollipops were the best Portland Maine souvenir for my kids from Portland Old Port.
I had to pick up these cute lobster lollipops for my kids! Photo credit: Marcie Cheung

We headed to Dean’s Sweets where we got to try their version of a Needham, a traditional Maine potato confection. Dean’s Sweets uses Maine Cold River Vodka (distilled from Maine potatoes) and it was delicious!

We also tried a salted chocolate truffle that was divine!

All tour guests get 10% off, so I grabbed a few lobster lollipops for my kids before heading out.

Why I Loved Portland Old Port’s Maine Food Tour

For me, a big part of travel is meeting new people. As they say, people bond over food. So, what better way to get to know other travelers than by doing a food tour of Maine?

Maine Foodie Tours keeps their tour group small, and that facilitates quality conversations.

I met an older couple from Maine who told me how they are doing a photo contest for Down East, a Maine magazine, where they have to take selfies in specific spots around the state. It’s called the Great Maine Scavenger Hunt.

Even though they live in Maine, their adventures have taken them to places they haven’t been before, and they even involve their friends and family.

Apparently, they have won the past couple of years!

Their prize? Huge poster collages of all their selfies, plus bragging rights!

These folks also brought their cousins on the Portland food tour. They were two sisters from California who were in Boston for a wedding and decided to drive 4 hours to cross Maine off their bucket list.

We talked a bit about family travel and how important it is to make good memories while traveling with kids.

And then there were two older ladies from Texas who asked when it gets warm in Maine. Like 80 degrees warm.

It was hilarious to see their reaction when our guide Chuck told them that’s a very rare occasion, maybe in August!

Portland Maine has lots of public artwork, like this lighthouse scupture in Portland Old Port.
Such a cute piece of public art near Monument Square in Portland Old Port. Photo credit: Marcie Cheung

How to Book Your Portland Old Port Culinary Walking Tour

It’s super easy to get advanced tickets to this Maine Foodie Tour. And you’ll want advanced tickets because they tend to sell out quickly.

This is about a 3-hour tour, and the stops will vary from day to day.

Reserve your Portland Old Port Culinary Walking Tour tickets.

If you go:


The Francis

For a Portland boutique hotel and spa, The Francis is a quaint 15-room inn.

They have family rooms and suites available, free parking, and they have a restaurant and bar on the property.

Portland Harbor Hotel

For Portland’s only AAA-rated 4-diamond hotel in Old Port, check out the Portland Harbor Hotel.

They have 24-hour room service, valet, spa, restaurant, and an Instagram-worthy lobby!

Old Port Style and Luxury

If you are looking for a Portland, Maine vacation rental, this one is right in the heart of Old Port.

It can sleep up to 6 people and is great for families with little kids. Easy walk to restaurants, attractions, and activities.



Because Portland Old Port is right near the waterfront, it’s extremely windy! I’m glad I wore a few layers with my North Face jacket on top!

Water Bottle

All the eating and walking will make you thirsty. I wish I would have brought my Hydro Flask with me.


If you are a light eater (like me!), you might want to bring a bag and some sort of container to take leftovers with you to eat later.


Lucky Catch Cruises

Have you ever wanted to learn how to catch lobsters? Hop aboard this fun, hands-on boat ride into Casco Bay, where you’ll learn the ins and outs of lobster fishing.

Plus, you’ll get to wear a real apron and gloves. And they have little lobster pants for kids!

Reserve your Lucky Catch ticket here.

Portland Explorer Tours

Want to see the most photographed lighthouse in Maine? Take a ride inside an air-conditioned van as you explore Portland’s famous lighthouses.

And you’ll also get a brief city tour. They have water and umbrellas available.

Reserve your Portland Explorer Tour tickets here.

Portland Fire Tours

Is there a cooler way to do a city tour than on a vintage fire truck? I don’t think so!

See the top sights in Portland, Maine, in the comfort of an open-air, covered fire truck. They even have authentic fire jackets and hats you can wear!

Reserve your Portland Fire Tour tickets here.

I hope you enjoyed learning about these Portland, Maine, Walking Tours! Check out my posts about  Lucky Catch Cruises, Portland Explorer Tours, and Portland Fire Tours!

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