48 Hours in Portland, Maine

I recently took a short vacation to Portland, ME for my mom’s birthday. This was my first time visiting the New England area and it did not disappoint me.

My mom visited last year for her birthday after reading an article in Bon Appetite magazine, “Where to eat and drink in Portland, ME” which gave tips on how to enjoy Portland in 72 hours. They laid out where to eat and drink in a very easy to do itinerary. So I’m going to share some of these tips with you!


How We Got There

There are no non-stop flights from Chicago (ORD) to Portland, Maine (PWM). I am NOT a fan of connecting flights and will do anything in my power to avoid them. Because we were traveling on Columbus Weekend, and that so happens to be a popular weekend for those that live in New England, airfare was crazy expensive. Expensive enough where I considered not going because it actually didn’t make sense to waste so much money. Then it hit me, fly into either another city, such as New York or Boston and take the train. The Amtrak train system is extremely popular and easy to navigate in the east coast. I played around with times and cost, and eventually came to the conclusion that flying in and out of Boston was the best choice. I was super excited because I had never been to Boston and also, because I found a flight that was just over $300…that was less than half of what I  would have paid flying into Portland. The Amtrak ticket was only $26 for one-way and I had enough points to cover half of my ticket! I just kept hitting gold!

Where We Stayed

Hyatt Place: This quaint hotel is situated perfectly in downtown Portland. You walk out of the street on to the main drag of all the bars and restaurants. The hotel was built within the past decade, so the lobby is up-to-date and spacious. There are two bars inside with plenty  of seating. The guest rooms are spacious and cozy. Perfect for a weekend getaway. The hotel also serves hot breakfast every morning–a nice cost savings! Portland isn’t a booming town of high-end five-star hotels, but I will say the Hyatt Place was definitely the closest to it.

Where We Ate

Okay! The restaurant scene in Portland is New England’s hidden gem. The obvious seafood scene is straight fire but even Japanese cuisine has made its’ mark in the town. Because I only had 48 hours, I needed to take full advantage of everything that was going on. I desperately needed to try everything I could get my grubby little hands on. And for the most part, I did! Check it out!

Eventide- Sit at the bar, have a beer, and order a dozen oysters, the lobster roll, the clam chowder and the New England Clam bake. The Clam bake can definitely be shared among two people-it comes with mussels, clams, salt pork, a lobster tail and potatoes. My mouth is drooling as I am typing this.

Gilbert’s Chowder House– This spot is a total local joint with no gimmicks. Get the Super Seafood clam chowder. It comes topped with shrimp, scallops and simple buttery flavors.

Scales– More of the higher end restaurant. Sits right on the water and inside are massive lobster tanks, pick out any of your liking. This place is beyond delicious and has the best

Dutch’s– Bon Appetite did not lie. Easily the best breakfast sandwich there is around! Chicken, gravy and biscuits make the heart grow fonder. The biscuit was light and fluffy and the chicken was freshly fried and pipe-in hot. The gravy had just the right amount of flavor bringing it all together. Make sure to get there right around the time they open. Trust me, there will be a line and it gets long, fast!

Crispy Chicken Biscuit

The Highroller Lobster & Co– I came across the popular food truck through a Thrillist video on Facebook. I saw them make this delicious looking lobster roll where the bun was made out of MELTED CHEESE! Yes, you read this right. Melted Cheese. So good! Follow them on Instagram as they will keep you up-to-date on their food cart location, the hours of when they will be there, and when they have sold out of food…which happens rather quickly.

The Honey Paw– Was just okay to me. My mom swears by it, but the menu just didn’t do it for me, Don’t get me wrong, the small bites that we ordered were tasty, but I won’t be rushing to go back. There are plenty of other Asian style restaurants to try.

Vena’s Fizzhouse– This place is more than just fabulous. The bartender, and forgive me, I can’t remember her name, but she  has to be one of the best mixologist’s I have ever come across. This place is a little off the main drag of Fore street and when you first walk in, it looks like just a regular storefront, but to your left is the upstairs bar. It definitely has a warm and cozy feel, making you never want to leave.


What We Did

While we spent the majority of the vacation eating and drinking, rightfully so, we did an old sail boat cruise from the Old Port. When my mom last visited a local told her that she should stop in a nearby grocery store, purchase a bottle of wine and a freshly carved turkey sandwich. She had the most spectacular time. So, I thought, why not do it again? We purchased tickets through Portland Schooner Company–they have some of the oldest sailboats in the New England area. The winds weren’t that strong that day, but it was still  so beautiful to be out on the water, eating and drinking once again.

Things I Wish I Could Have Done

I really wanted to visit a wholesaler and pick out some fresh lobster and have it delivered to my house when I arrived. I talked to many people about how to go about it. But 1.) I ran out of time and didn’t get a chance to visit the markets. 2.) I don’t think I have the heart to drop a live lobster into a pot of boiling water. I loved Sebastian way too much to think about doing that to him…but yet he was pretty tasty 🙂



I had the most wonderful weekend hanging out with my mom. It has been a while since, I traveled to a brand new city in the United States. I can easily say that the people and of course the food, stole my heart. I now understand why my mom fell in love with this place. If you haven’t been to I am already planning my next visit.

If you’ve traveled to Portland and have any recommendations for my next visit, please feel free to share in the comments section below! Until next time…xoxo

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