Best Things to Do in Portland, Maine | My Top 10 List

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!