For the longest time, Maine wasn’t really considered a travel destination. It was too far east and too far north. Too cold. Too folksy. But over the couple decades, Maine has become known as an old school east coast Americana gem. It’s part small town, part cultural hub, part port town, and so, so much more.

If you’re headed to Portland, Maine in the next few months, I have put together a list of the best things to do in Portland ME based on my experience there. Below you’ll find recommendations on tours, places to eat, places to sightsee, and what to do to make your trip to Portland unforgettable. You can watch my video below or view my list of top 10 things to do in Portland Maine below.

The Real Portland Tour is the only sightseeing tour in Portland Maine that includes a full city tour and a trip to three of the lighthouses.

“So to tell me what the Real Portland Tour is.”

“It’s the real deal – I’m a real local born and raised.”

We got to see the full city tour of Portland. From the bustling downtown area and eclectic shops, to the art district, to the world class restaurants and bars.

Then Derek took us out along the Casco Bay to see its islands and forts on the way to the Portland Headlight.

Derek from the “Real Portland Tour” – he’s so cool – he has all of this information. He knows so much about the city. He’s originally from here and he’s a librarian. So the amount of facts that he knows and everything that he can tell you about the city…he talks about the “hah-bah,” and he’s going to the “pahk.”

He was so knowledgeable and interesting and had the greatest stories about the town where he grew up. Definitely put the Real Portland to her on your list.

Also while you’re visiting Portland, you have to check out the gorgeous lighthouses along Casco Bay. It’s gorgeous. You can take a tour, you can drive yourself, sometimes in the summer you can bike.

The rugged Maine coast is known for its beautiful lighthouses, and just outside of the city of Portland along Casco Bay is the Portland Headlight. It’s the most photographed lighthouse in the entire US of A.

And another great Lighthouse to visit is the Spring Point Ledge. Only on the weekends you can actually walk out there. You have to jump in the different rocks to make it all the way out.

This is just quintessential Maine. This is why you come to Maine. It’s what you see in all the pictures, so definitely worth checking them all out.

Portland Maine is a foodie town for foodies. In 2018, Bon Appetit listed it as the restaurant city of the year.

And did I say I like to eat? Some of their most well-known restaurants include Central Provisions, Fore Street Eventide, Street and Co., and Duck Fat. There was so much delicious seafood – lobster, oysters, and fresh fish.

While I was there I actually had two lunches and two dinners on two different days.

A little tiny secret but don’t tell anybody (shhhh!) is to come to the top of the parking lot at the customs house for the best view of downtown. Just across the street from the beautiful Customs House is a nondescript parking garage. If you go to the top level, its open-air and you can see the spectacular views of all the city roofs throughout downtown Portland

Another great thing to do while you’re in Portland is to go on the Maine Foodie Tour.

This morning I’m on the Bon Appetit tour which starts at 10:30 in the Munjoy neighborhood. Most of the food in Portland is all about the seafood but this is a very unique tour that gives you croissants, clams, a little bit of Tex-Mex, and some other exciting things.

You even get to go to a kombucheria.

And what’s crazy about this picture is the fact that, if you can see behind me, it is a longhorn flag from the University of Texas (Hook ‘em Horns!) and we are here in Portland, and we’re checking out a Tex Mex restaurant. Austin girl. Tex Mex restaurant. It’s a match made in heaven. Yum!

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And next item on our list are the infamous east coast oysters. I recommend two different places to get these incredible little morsels. The first is the Shop which is about a 10-minute Uber ride from downtown Portland and all of their oysters are a dollar fifty all day long. We’re at the shop now and they are famous for their oysters. Their oysters are dollar 50 everyday all day long do matter what you order and they also have a hand something or other. They have tuna.

We order the calamari in a ragu. The coup de gras is…I have two orders of everything they have on the menu. I cannot wait to dig in.

The other play to try the oysters is at Scales, which is right there on the Harbor. So tonight we’re at Scales and we heard that they have the best oysters in town and I have to say that these two may be the best oysters I’ve ever had in my entire life. They’re really good. They’re amazing.

Yeah, when you come to Portland, food is the way to go. And oysters are only a dollar during happy hour. We had so much fun eating our way around the city

The next thing that you have to do when you’re in Portland is to go on the Lucky Catch Cruises. This is well worth the trip and it’s so fun to go out in Casco Bay and learn how the lobstermen catch your dinner.

The Lucky Catch Tour has been around for more than a decade and honestly it’s one of the best things that I did during my visit in Portland, Maine. It’s also a great value.

If you’d like to know more about Lucky Catch Cruises make sure to check out last week’s video. It’s all about my tour traveling with Captain Brian and Kate.

Crazy little tidbit about Portland is that the pedestrians always seem to have the right of way. It doesn’t matter whether you actually have the green light to go or not!

And then there’s more food. I’m now at the Holy Donut that is famous for putting a potato – shredded potatoes in a sugar donut. The best part about it is they have gluten-free just for me.

It’s like not exactly cooked all the way through here so I can get that sort of gooeyness to it and then it’s just..I mean it’s just ridiculous. If you’re gluten-free and you come to Portland, Maine, not only do you have to eat the delicious seafood and the oysters, you have to come to Holy Donut and get a gluten-free donut.

So let’s talk bars in Portland – actually, let’s talk speakeasies in Portland.

In Portland, Maine, it was one of the first cities to have prohibition in the entire country so they are known even to this day for the speakeasies. Definitely check out Lincoln’s while you’re in town.

Portland is such a walkable city. I recommend staying in town. You don’t need a car and it feels 10 minutes walking distance.

And next is more food, but this time it has a Texas twist.

It’s been quite a morning here in Portland. It’s been raining and it’s really, really cold. It’s May and it is about 35 degrees here. Not good weather for the Texas girl in me. But right now, I’m headed to warm up and I’m going over to the Highroller Lobster Company.

It’s only been around a few years. It used to be a food trailer and now it is brick and mortar and the reason I keep looking down is because I was told to come and get the most delicious lobster taco. And instead of a taco shell it is a grilled cheese.

(Euphoric music plays)

I got the jalapeno mayonnaise and the lime mayonnaise, so I get a little bit of Texas here in Portland, Maine. There must be like 6 lbs of lobster on this. It is so friggin’ good. You definitely have to try this. Cheers!

#1 The Best City Tour in Portland, Maine

The Real Portland Tour is the only sightseeing tour in Portland, Maine that includes a full city tour and a trip to three of the lighthouses. We got to see the full city tour of Portland, from the bustling downtown area and eclectic shops to the art district and the world-class restaurants and bars. We headed out to Casco Bay to see its islands and forts on the way to the Portland Headlight.

Our tour guide, Derrick, was amazing! He knows so much about the city for two reasons:

  1. He’s a local, born and raised
  2. He’s a librarian! He was so knowledgeable and interesting and had the greatest stories about the town where he grew up.

Definitely put the Real Portland Tour on your list!

#2 The Best Lighthouses in Portland, Maine

Also while you’re visiting Portland, you have to check out the beautiful lighthouses along Casco Bay. You can take a tour like I did, you can drive yourself, and sometimes, in the summer, you can even bike! The rugged Maine coastline is known for its beautiful lighthouses and just outside of the city of Portland along Casco Bay is the infamous Portland Head Light. Did you know it’s the most photographed lighthouse in the entire US?

Another great lighthouse to visit is the Spring Point Ledge. On the weekends, you can actually walk out there you have to jump on the different rocks to make it all the way out. It’s very picturesque and definitely worth checking them all out.

#3 The Best Restaurants in Portland, Maine

Portland is a foodie town for foodies! Did you know that in 2018, Bon Appetit listed it as the restaurant city of the year? Some of the most well-known restaurants include:

There was so much delicious seafood, lobster, oysters, and fresh fish while I was there that I actually had two lunches and two dinners on two different days!

#4 Best View in Portland, Maine

Fourth on my list is a little well kept secret: Come to the top of the parking lot at the Customs House for the best view of downtown! The parking garage is just across the street from the beautiful Customs House. If you go to the top level it’s open air and you can see the spectacular views of all the city routes throughout downtown Portland.

#5 Best Food Tour in Portland, Maine

5th on the list is to go on a food tour! I went with Maine Foodie Tours on the Bon Appetit. Most of the food in

Portland is all about the seafood but this is a very unique tour that gives you croissants clams a little bit of Tex-Mex and some other exciting things. You even get to go to a kombucharia.

#6 Best Oysters in Portland, Maine

Next on our list are the infamous East Coast oysters. I recommend two different places to get these incredible little morsels.

  1. The Shop which is about a 10 minute Uber ride from downtown Portland and all of their oysters are $1.50, all day long.
  2. The other place to try the oysters is at Scales which is right there on the harbor. While in town, I heard that they had the best oysters in the whole city. My opinion? They may be the best oysters I’ve ever had in my entire life! The oysters are only $1 during happy hour.

#7 Best Boat Tour in Portland, Maine

The next thing that you have to do when you’re in Portland is to go on the Lucky Catch Cruises. It’s so fun to goout in Casco Bay and learn how the lobster man catches your dinner. The Lucky Catch Cruise has been around for more than a decade and honestly, it’s one of the best things that I did during my visit to Portland. It’s also a great value! If you’d like to know more about Lucky Catch Cruises, check out last week’s video and blog here.

#8 Best Dessert in Portland, Maine

Then there’s more food! If you’re in the mood for something sweet, head over to the Holy Donut. They are famous for putting shredded potatoes into their Donuts. If you’re gluten-free like me, they have several options for us, too!

#9 Best Bar in Portland, Maine

Now let’s talk bars in Portland. Actually, let’s talk about speakeasies! Portland, Maine was one of the first cities in the entire country to have prohibition so they are known even to this day for the speakeasies. My top choice is Lincoln’s.

#10 Best Taco in Portland, Maine

Our last thing to do is another food item, but this time it has a Texas twist. Head over to the High Roller Lobster Company which started as a food trailer. Now it is it’s brick-and-mortar and I was told they serve the most delicious lobster taco. Instead of a taco shell, they use grilled cheese to hold the lobster meat and toppings. And if you love tacos like I do, check out my video and blog on the Top 5 Tacos in my hometown of Austin, Texas.

I hope you enjoyed my list of the best things to do, see, and of course TASTE in Portland. Share in the comments if you’ve been to any of these places!

Travel Tips & FAQs for Portland, Maine

Where to eat in Portland ME?

Start by watching the video at the top because Portland is a FOO-DEE-TOWN. 

I can highly, highly recommend the following establishments: Highroller Lobster Company, Holy Donut, The Shop, Scales, Central Provisions, Fore Street, Eventide, Street & Co., and Duck Fat. If you want a great starting point, I highly recommend you try the Taste of Portland Food Tour by Bon Appetit.

What to do Portland ME?

Do you like eating? Drinking? Seeing historic architecture? Maybe lobster fishing is more your speed. As a coastal town, Portland really has it all. Great tours and activities for tourists, plenty of places to relax, eat, hang out, drink and more. Honestly, your best bet is to get a place somewhere downtown and just walk around. You won’t have a dull moment.

Where to eat lobster in Portland ME?

Maine is lobster central. I can personally recommend Central Provisions, Highroller Lobster Company, Fore Street, Eventide, Street & Co., and Duck Fat. All offer approachable and amazing seafood offerings that highlight the local catch. 

If you’re looking for something a little more high end, try out the Back Bay Grill, Emilitsa, and Union Restaurant.

What airlines fly to Portland ME?

Portland ME isn’t a huge hub for airlines or international travel. Luckily, plenty of domestic carriers offer direct flights to Portland International Jetport (PMW). They include: American, United, Delta, Frontier, Southwest, Sun Country Airlines, Jet Blue, Cape Air.

What county is Portland ME in?

Portland Maine is located in Cumberland County.

How far from Portland ME to Boston MA?

There are a lot of different ways to get from Boston MA to Portland ME and vis a versa. You can fly, drive, take a train, or take a ferry. To simplify things, it’s a 2 hour drive from Portland to Boston, which is often the quickest and cheapest way to get between the two cities.

How far from Portland ME to Bar Harbor?

It is a little over 3 hours to drive Portland ME to Bar Harbor, a noteworthy town on the Atlantic Ocean and at the start of the Acadia Mountains. This drive is a popular tourist track to see a lot of historic coastal towns along the way.

 

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