10 Things To Do in Portland, Maine in 24 Hours

Good morning! Did you catch my Instagram pictures from this weekend? We had an awesome 24 hours in Portland, Maine this past weekend. We loved everything from the food, the cocktails, to the boutiques, friendly people, and the scenery! It’s a wonderful little get away for us, being that it’s just a two hour drive from Boston. 


Before I get into my 10 places you must go to, let’s talk about accommodations and some other little details!


Where we stayed: 

We stayed at the Portland Regency Hotel & Spa, which is part of the Historic Hotels of America. They have valet for your car which you can come and go as you please, friendly staff, and tons of history! It was beautiful, clean, had an awesome bar called The Armory, and it is in the BEST location. It is right in the heart of all the shops, restaurants, and just exactly where you want to be situated for a night in Portland. Our room had a really nice balcony which you can sit at and enjoy coffee and a newspaper in the morning. Next time we come, we are definitely taking advantage of the spa, which has a sauna, steam room, and all of the awesome spa amenities you’d be looking for!



 Portland is such an awesome city because within the 24 hours we were there, we felt like we knew already our way around! There is so much to do in this city. It felt like a smaller Boston with tons of character. P.S. They do have Uber, but with where we stayed we easily walked everywhere we wanted to go. 

Are you ready? 10 things you definitely need to do, plus some pro-tips to go along with it!

I recommend getting small plates or sharing, so you can check out a variety of places. Keep in mind that most places do not take reservations so be prepared for a bit of a wait. Also keep in mind that this is from a foodie perspective, so we did a lot of eating 😉

1. Have fries at Duck Fat

I wouldn’t go here for lunch (if you eat like me), since it’s mostly paninis. Their poutine and fries are worth checking out though for sure. Pro tip: While waiting, have a drink next door at East Ender. May I suggest the Lemon Drop Martini! It was one of my favorite cocktails of the trip.

2. Have a cocktail and a bite at Eventide Oyster

We ordered the Lobster Stew which I cannot wait to recreate. Mike and I agree this was definitely a favorite. He loved the old fashioned he ordered, and I got their version of boozy lemonade.

3. Grab a donut at The Holy Donut

The gluten-free chocolate sea salt is INSANE.

4. Walk around Old Port

There are awesome little boutiques, tons of fun stores to pop into, and of course more restaurants and unique bars to try. Milk Street, Market Street, Exchange Street, and Congress Street are where we spent most of this time. We liked Motifs for little fun gifts!

5. Pop into Central Provisions for a cocktail and a snack

We ordered the spicy raw beef salad and the bluefin tuna crudo- both were excellent! Mike had a Bloody Mary and I had one of their fun cocktails.

6. Head to Bam Bam Bakery for a gluten-free treat

We had the Espresso Chocolate Chip Muffin and it was delicious.

7. Head 20 minutes out to Cape Elizabeth and check out the gorgeous Portland Head Lighthouse and scenery

This is an awesome warm-day activity. 

8. Go to Vena’s Fizz House for a cocktail!

The owner Steve is SO friendly and will school you on everything you need to know about bitters in 20 minutes.

9. Have brunch at Bayside American Cafe (formerly known as Bintliff’s)

We came here Sunday morning before heading out. We got there around 9:15 and had a 20 or so minute wait. By the time we were there for 10 minutes, the wait went up to 45-1 hour! Get their early or be prepared you might have to wait! It’s worth it. We tried a few things that were all fantastic, but their homemade smoked salmon was out of this world.

10. Grab another donut at The Holy Donut 

Yes, I’m serious.


Places we didn’t make it that we are definitely getting to next time: 

  • Boda (Thai) for a meal

  • Hunt and Alpine for a cocktail

  • Fore Street for a cocktail and food

  • I also heard that Grace, Street & Co, and Fifty-Five are phenomenal choices.

  • Another suggestion we received was to take the mailboat tour which brings mail to all of the small surrounding islands. We heard it’s really wonderful (and it’s BYOB), but it was a little too cold for us to brave. Plus, with only 24 hours, we wanted to explore the town more.




This is not a sponsored post. We did receive complimentary hotel accommodations. All opinions are 100% always my own.

Have you been to Portland, Maine? What was your favorite thing to do?



October 20, 2015

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33 Responses

  1. Just recently went! Alpine had my fave cocktail of the whole trip, you’ll have to go back there! We Also hit duck fat for late night fries, central provisions for the delish beef and eventide! Oh and yes holy donut too! sounds liked the same trip haha, even stayed at the same hotel.

      1. Oh, totally forgot Vervacious–did you go there? All homemade/small batch spices, rubs, balsamics, etc…all in gorgeous glass jars and you could sample everything.

  2. I just moved to Portland a few months ago and love it! Would recommend all of the above, and also Lincoln’s which is a speakeasy with a secret entrance or The Bearded Lady’s Jewel Box for unique atmosphere, cocktails, and snacks. And a trip to Peak’s Island is always gorgeous!

  3. Awesome post, thank you Lexi! We are going at the end of November for my birthday weekend so all this information will for sure come in handy as I’m planning the weekend!!! Perfect timing 🙂 I saw all your Portland posts on instagram too, looks like such a fun city!

  4. You need to go to Soakology! Best leg and foot massage after soaking in a tub of rose water… While drinking tea with cookies. I try to make it there every time I make it to Portland!

  5. Just saw this post after discovering your blog today. SO love your rave for my hometown. It has become a super cool little coty in the last 20 years. And yes. Holy Donut. Just yes. 🙂

  6. You have to go on a Lucky Catch tour next time you’re in Portland! It’s the reason we keep going back. Who wouldn’t want to catch lobsters and get to eat the freshest lobster you can? 🙂

  7. while in Portland, you have to eat at Silly’s!! You will walk in and be completely distracted by the ridiculously amazing atmosphere….but their Gravy Danger fries are out of this world. Their gluten free crust is so good! I don’t think I’ve had anything that wasn’t absolutely amazing there! Hope you guys enjoy it too!!!

  8. We grew up in Maine but live in PA now. We go back every year and it just keeps getting better each time we visit! Portland has a wonderful farmers market at Deering Oaks Park every Saturday. Also, we love Becky’s on Commercial St for breakfast!

  9. Love Portland, ME. Our son and daughter-in-law live and work there. You must eat at Hot Suppa for breakfast and have their Corned Beef Hash. It is by far the BEST I have ever had. Don’t forget to see Portland Head Light and have make sure you eat some Lobsta Rolls. Biking around Peaks Island and visiting the little shops is fun. Lots to do there!!

  10. My son went to College in Maine and I miss going there to visit. Absolutely love it especially all the little shops!! Would like to move there one day and be able to breathe in all that fresh air all the time! Planning a visit soon!

  11. The Holy Donut is our FAV!! We are from Georgia and ate there 3 years ago. We tell anyone and everyone who will listen to go there!

  12. Awesome post! My fiancé and I are thinking of taking a trip to Portland Maine for our honeymoon! Excited to start the planning process!

    Maybe I missed it, but what month did you visit?

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