By Golly, Ollie!

Eating donuts, BBQ, pizza slices the size of my head, and playing pinball barely scratch the surface of what we did during our vacation in Maine last year. If you’re planning a trip to Portland, Maine, be sure to check out these places as well:

Where to Stay

Inn at St. John | 939 Congress St. Portland, ME 04102

The Inn at St. John is Portland’s oldest, continuously operated inn. It’s an old, Victorian building  located on the northwest side of downtown Portland, which is fairly removed from where most of the restaurants, shops, and nightlife are located– about a 25 minute walk. What initially drew us to this hotel was the price; the Inn at St. John is about $100/night cheaper than the rest of the hotels in the city. What would keep us coming back (aside from the price) is the incredibly kind hotel staff, the most comfortable bed ever, and these cozy bathrobes! The Inn at St. John comes so highly recommended on Trip Advisor and Google, and it’s worth every star. Plus, the savings in hotel accommodations allowed us to splurge in other areas.

Inn at Diamond Cove | 22 McKinley Ct. Portland, ME 04109

We spent a few days in downtown Portland, Maine, and then we hopped a ferry out to Great Diamond Island to stay at the Inn at Diamond Cove. The stars must have aligned because when we arrived, we learned that we got a free upgrade from our King Room to a King Suite. Aside from a king size bed that swallowed us whole and a shower with the dreamiest shower head ever, which would have come with the room we booked, the suite also had a kitchenette stocked with dishes and cookware, a dining area, a balcony, and a living room. I have never stayed in such luxury before, and I swear, it was bigger than the apartment we were living in at the time.

The Inn at Diamond Cove also offers a lot of extra amenities like bicycle rentals (since motor vehicles were not allowed on the island), a recreation room with duckpin bowling, ping pong, and PINBALL(!!!), tennis courts, an indoor basketball court, a pool and hot tub, and so much more.

To top off the experience, Inn at Diamond Cove had some of the nicest staff, and the greeting at the ferry when we arrived set the tone for the customer service experience. One of the staff members helped us load up our luggage into a golf cart and drove us to the hotel; along the way, she gave us a little history about the island and pointed out places to check out as we explored the island ourselves. I also recall spending all evening downstairs at the lobby bar drinking Moscow Mules and chatting with the bartender. (True story: one of them went to school at Western Michigan University, which is my alma mater; small world, right?!)

Where to Eat

Bayside American Cafe | 98 Portland St. Portland, ME 04101

Jon is notorious for packing the wrong kind of shoes for walking during vacation, so by the end of the first day, his feet were aching. Later in the week, when I suggested we walk to Bayside American Cafe for breakfast, which was a mile away from the hotel, he made sure to express his displeasure. And then, when we arrived we discovered we had to stand in line just to get a table at this popular brunch place. The trek and the wait was worth it though; Bayside served the best breakfast we had the pleasure of eating while in Portland. Make sure to try their Classic Eggs Benedict and Rocket Fuel coffee. And if you’re in need of a little hair of the dog, try out their Absolution, which is a mimosa with Absolute Raspberry and a splash of grenadine or the Honeymoon, which is Maine Meadworks wildflower honey mead and Brut champagne.

The 5 Spot | 935 Congress St. Portland, ME 04102

When hunger struck us late at night, and we were too tired to trek to the east side of downtown Portland, we walked next door to the 5 Spot for authentic Philly Cheesesteaks (the kind made with cheese wiz). I also had my first taste of Moxie, which was an experience in itself. Moxie starts out tasting like root beer but then morphs in to something herbaceous and medicinal. I liked it, but I might be in the minority.

Hot Suppa | 703 Congress St. Portland, ME 04102

If you find yourself craving grits while in Maine, make sure to visit Hot Suppa for some Southern-inspired cooking. Even if you’re not craving grits, go to this restaurant and order their impeccable Geechie Boy grits. I also had my first taste of kombucha here; I’ve never seen that on a menu before.

Gelato Fiasco | 425 Fore St. Portland, ME 04101

Is any vacation complete if you don’t consume at least one scoop of ice cream or gelato? Probably not, which is why you should visit Gelato Fiasco. The Gelato Fiasco offers irresistible flavors like Dark Chocolate Sea Salt Caramel Gelato, Maine Wild Blueberry Crisp Gelato, and Torched Marshmallow S’More Gelato. Side note: I just learned that Gelato Fiasco ships their Gelato nationwide. Be still my beating heart!

Inn at Great Diamond Cove (Lobby Bar) | 22 McKinley Ct. Portland, Me 04109

On top of living in luxury for a few days at the Inn at Great Diamond Cove, we also feasted like kings. Jon ordered the lobster roll for lunch and dinner, and if it were offered for breakfast, I’m sure he would have ordered it then too.

Things to Do

Portland Museum of Art | 7 Congress Sq. Portland, ME 04101

The Portland Art Museum is perhaps one of the best art museums I’ve visited. Sure, I’ve been to the Art Institute of Chicago, and sure, that collection is incredible. But, if you’re looking for a well-curated collection that you can view in one day, the Portland Museum of Art has it. I think my favorite part of the PMA collection was the pieces showcasing Maine’s artists.

The Green Hand Book Shop | 661 Congress St. Portland, ME 04101

The Green Hand Book Shop offers an eclectic collection of second-hand books. There seemed to be a book for every kind of customer. I found myself drawn to the children’s book section because it had so many books I remember reading when I was four or five. I didn’t leave empty handed…

Soakology | 511 Congress St. Portland, ME 04101

Remember when I said Jon is notorious for packing the wrong kind of shoes? Well, after dragging him a mile to breakfast, I promised him a foot soak and massage at Soakology. We also got to sip on hot tea while relaxing. Jon had a refreshing ginger mint tea, and I had an enticing pine smoked black tea. Jon experienced a second wind after that, and he wasn’t so grumpy as I dragged him around the city more.