We have a goal of crossing off all 50 U.S. states, all 7 continents, and as many countries and experiences as possible. Of all the states we've explored so far, this one stands out as one of the most memorable. From the stunning coastline and historic landmarks to charming lighthouses and new, unforgettable experiences, it was an unparalleled weekend getaway with my best friend.
🏨 Where We Stayed
For this trip, location was everything. We wanted a hotel within walking distance of the places we planned to explore, and the Holiday Inn Portland – By the Bay was the perfect fit. It gave us easy access to the heart of the city while offering great amenities like an indoor pool, 24-hour fitness center, and an on-site restaurant and lounge. We spent most of our time out and about, but it was so nice to come back to a place that checked all the boxes.
🍽 Our Favorite Foodie Finds
The Holy Donut
Before our trip, nearly every travel guide and local recommendation pointed us to
The Holy Donut - and once we arrived, we saw why. People everywhere were walking around with their
signature boxes, and yes, the line was out the door. But don't let that scare you off - the line moved quickly, and the wait was
absolutely worth it. We grabbed a box to-go for our trip home, and it made for the perfect sweet send-off from Portland.
Three Dollar Deweys
If you're in need of a laid-back lunch spot,
Three Dollar Deweys hits the mark. This
casual pub-style restaurant offered exactly what we were looking for—no frills, just
good food in a comfortable setting. The menu had all the pub favorites you’d expect, from hearty sandwiches to classic comfort food, making it the perfect midday stop to refuel and relax.
The Highroller Lobster Co
You can't visit Maine without trying its most iconic dish: the lobster roll. The Highroller Lobster Co is the perfect place to dive in. This casual, counter-service spot serves up fresh, flavorful lobster rolls with a creative twist. With fun patio seating and a laid-back vibe, it's a great place to enjoy the local flavors and soak in the Portland atmosphere.
Shipyard Brewery
One thing we love to do on our travels is check out
local breweries - they're the perfect way to experience a city's personality through its craft beer scene. After a full afternoon of exploring, we made our way to
Shipyard Brewery, and it was just the relaxed, laid-back vibe we needed. The pub was
spacious and welcoming, with plenty of seating and a great atmosphere. With so many beers on tap, we couldn't choose just one - so we ordered a
tasting flight and sampled a variety of local brews. A perfect way to rest before more exploring!
DiMillo's On the Water
What better way to soak in the coastal charm of Maine than by dining on the water - literally. DiMillo's On The Water offers a unique experience aboard a docked boat-turned-restaurant, combining fresh seafood with panoramic harbor views. It's the perfect spot for a memorable meal with a true taste of Portland. Highly recommend!
🦞 Exploring Like A Local
Stroll the Scenic Wharfs
One of the best ways to take in the charm of Portland is with a leisurely walk along the waterfront. The area is lined with a series of historic wharfs—Union Wharf, Chandler Wharf, Widgery Wharf, and more—each offering a unique blend of seaside views, restaurants, boutique shops, and stunning boats docked in the harbor. It’s the perfect way to slow down and soak in the coastal atmosphere.
See a Piece of the Berlin Wall
Tucked along one of the many piers in the Portland Harbor, a powerful piece of history quietly stands - a segment from the Berlin Wall, demolished in 1989. As you stroll the waterfront, you'll come across this unexpected landmark, a reminder of a divided past and a symbol of unity, right in the heart of coastal Maine.
Visit the Portland Head Light
Maine’s northeast coastline is rich with historic landmarks, and its lighthouses are some of the most iconic. The
Portland Head Light,
one of the most photographed lighthouses in the country, has been in operation since 1791. Nestled within
Fort Williams Park, the lighthouse also features a
small museum where you can learn more about its fascinating history. While we didn’t get a chance to walk the grounds ourselves, catching a glimpse of it from the water was just as magical.
Lobster Fishing
No exaggeration - this is
one of my absolute favorite memories from not just this trip, but maybe ever. My dad is an incredible fisherman and growing up in the Midwest, he taught my siblings and me how to fish. But
lobster fishing? That was a whole new world (cue the song from
Aladdin).
We boarded a small boat with a friendly crew and a handful of fellow tourists for a few hours out on the water. They walked us through the entire process - from how the traps worked, to pulling them up, swapping out the bait, and even banding the lobster claws (so no one went home with a not-so-fun souvenir).
One fun (and slightly chaotic) moment? Swapping out the bait. Fair warning: the seagulls know the drill and aren’t shy about swooping in for the scraps. It added a whole new level of excitement to the experience!
It was such a unique and fascinating experience. Even if you're not much of a fisherman, it's an incredible way to get out on the water and learn about the daily life of Maine's coastal community.
The best part? At the end of the tour, you have the chance to buy one of the lobsters you helped catch and take it to a nearby restaurant where they'll prepare it for you. It doesn't get any fresher than that!
Final Thoughts
If you're craving a getaway with a slower pace, new adventures, and some of the freshest seafood around, Portland is calling your name. We only had a weekend to explore, but in just a short time, we created some truly lasting memories. It’s the kind of place that makes you want to come back before you’ve even left.
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