Last weekend was spent in Portland, Maine to celebrate our anniversary. Admittedly the winter/spring season is not the most popular season to explore Portland but nonetheless, still a fantastic city to visit.
Where To Stay
I cannot say enough good things about staying here. The hotel is a old newspaper press transformed into a hotel and somehow during the renovation, maintained all the charm. Typewriters adorn the wall and the front desk keyboards are even typewriters, too. 
I’ve never stayed at a hotel where the front desk team has been more accommodating. Upon checking in, we were informed our room had been upgraded to a suite with a bottle of wine & two glasses waiting. The rooms are a perfect combination of space & cozy with white marble heaven for a bathroom. The hotel is in a perfect start to walk everywhere and they also provide a shuttle, which will even drop you off at the airport.
Where To Eat
Let me say, overall, the food in this city is to die for. I’m sure there are places we may have missed due to the season we visited, but all my recommendations below are out of this world.
Great lunch spot. After we landed & checked in to Press, we headed straight for Duck Fat. While there is normally a wait, we were lucky and only waited about 15 minutes.
Personal Recommendation: order off the specials menu, while everything on their menu is amazing, their specials list is to die for. I had a buttermilk & strawberry milkshake and our waitress told me the fresh strawberries had been brought in an hour before we got there. It was so delish!
Right down on the water. This is a great spot if you have a larger party as a lot of restaurants in Portland are small and easily accommodate 2-4 but could be tight if you have more people.
Personal Recommendation: Again, ask for their specials. Highly recommend the obvious, fish & seafood.
This is a MUST! Tapas style, I highly recommend stopping in for lunch. They don’t take reservations, so go early or be prepared to wait. If you’re a real foodie or just enjoy the cooking/ preparation process, ask to be seated at the chef’s bar. The preparation of these beautiful dishes between all the chefs is mind-blowing. Every dish is more beautiful than the next.
Personal Recommendation: Their menu changes daily but if it’s listed, you must, repeat, must have the roasted cauliflower. I know it sounds like it could be a boring dish, but it’s incredible. Also, the winter salad is just as tasty as it is beautiful. (pictured above).
A trip to Maine wouldn’t be complete without a lobster roll. While there are some amazing seasonal places, we missed their opening by about a week. Almost everyone we talked to recommended Eventide and it was just as delicious as they promised.
Personal Recommendation: Brown Butter Lobster Roll. No explanation necessary.
This restaurant is an absolute MUST! If I could recommend only one place, this would be it. Reservations are usually booked out up to 4 months in advance and require a $50 deposit, however, the restaurant keeps 1/3 of their tables open per evening for walk-ins. We went at 5pm when the bar opens to put our names down and were surprised to see a line already formed of 12 or so people. We put our name down and were able to get in within an hour.
Personal Recommendation: Ask for the specials/ waiter’s recommendations. I had a local Arctic Char and it was incredible. Dave & I said our meals were the best of 2018 and maybe even all of 2017, we couldn’t think of any meal that topped it.
We stopped in here to grab a drink while we waited for our reservation at Fore Street. Great cocktails and fizzes and almost everything can be made with or without alcohol, whichever your preference.
This teeny southern-style will definitely have a wait. If you follow my directions below on where to drink, plan to go to Hot Suppa the next morning and heal your hangover. Their Bloody Mary has won multiple awards and just about everything on the menu will make your mouth water just reading it.
Personal Recommendation: Sure to heal your hangover, order The Mother Clucker + their Bloody Mary. Trust me.
Let me start this portion off by saying, I DO NOT LIKE DONUTS. I know. It’s the one sweet I’ve always been able to pass on. When people found out about my trip to Maine, everyone (and their mother) was begging me to stop by Holy Donut and assured me that potato donuts are much different than regular donuts. When in Rome, right? Saturday morning, we stopped by and tried the Lemon and Ginger Glazed Sweet Potato Donuts which were delish. Before we left on Sunday, we wanted to try one other and the line was out the door! We thankfully decided to get their chai donut which was unbelievably amazing. Really wishing I had brought a box home with me.
Personal Recommendation: Chai Donut and if you’re a coffee drinker, an iced coffee. The ice cubes are frozen coffee!
Where To Celebrate (read: drink!)
You had to know I loved this sheerly by the name, another B&B! This newly opened bar is right on Exchange St. so if you’re staying at the Press, a quick walk down the street. The deep navy decor, marble countertops and wooden bar make the atmosphere chic yet cozy and there’s no question if the crew behind the bar knows what they’re doing; the drinks were incredible. We stopped in for happy hour and by the time we left, the place was packed. Definitely a Portland hot spot not to be missed.
Personal Recommendation: Young Burrows
This neighborhood jaunt was recommended to us by the owner of Portland Trading Co. Scandinavian in nature, the kitchen offers some delicious treats as well as local beer & spirits. Their kitchen stays open until they close at 1am, so a great stop if you need a light snack with your nightcap.
Personal Recommendation: Popcorn + Champagne (as heavenly as it sounds)
Fun brewery/ distillery right on Commercial Street. Great for flights of beer or a local cider or kombucha, if you’re a non-beer drinker like me.
Literally, hidden down an unmarked stairwell behind a bookcase, this speakeasy isn’t known for it’s craft cocktails but rather for it’s dark atmosphere, loud music and $5 drinks. Yes, everything is $5.
Personal Recommendation: Don’t try to take a picture, the bouncer will stop you.
Other breweries that were recommended to us but we didn’t make it to:
Where To Shop
Portland Trading Co. – men & women’s clothing, plus apothecary & accessories
Portland Dry Goods – men & women’s clothing
Sea Bags – adorable totes made out of recycled sail cloth
Gus & Ruby – incredibly beautiful paper goods
What did I miss? What are your favorite spots in Portland?
Cheers
I was just there about 2 weekends ago! I loved Hot Suppa. A great place for Lobster with an edgy feel is The Highroller Lobster Co. Another great place I went to is Slab which has 1lb pizza slices that are so airy and fluffy it was amazing I brought a slice home!
Thanks so much for sharing!! I definitely heard of those two places- just wish we had more time ( and bigger appetite :))