Portland Maine Guide: 72-Hour Itinerary, Events, Real Estate & Pets

She Came to Visit. Here’s How We Spent 72 Hours in Maine.

From Portland to Bath to Five Islands, no itinerary, no reservations, just three days of croissants, lobster rolls, and long walks in the heat.

My sister drove up from Connecticut with her boyfriend and a bag of snacks. She’s smart, funny, and kind in a way that makes restaurant waiters want to hang out with her. She’s also down for anything. No rigid plans. No bad moods. Just the kind of person you want to show your home to.

So I gave her my version of Maine: three days, no itinerary, just a loose map of good food, random surprises, and some of my favorite places. If friends or family came to visit you, where would you take them?

Here’s how ours unfolded.

Day One: Zu + Fireworks

They pulled in on the Fourth of July. Last time she visited, Zu Bakery was closed ( holiday hours and heartbreak ), so this time I made it a mission. I got up early and grabbed a box of croissants before they hit town. We stood around the counter eating them like kids at snack time. No plates. No talking. Just flaky silence.

We had a BBQ planned at my house, so we walked to Rosemont for some last-minute cookout stuff. Friends came by. We grilled Caribbean jerk chicken with plantains, built some killer salads, and opened bottles of Maine wine. I’m thoroughly impressed with both my friend’s cooking skills and the hospitality of Portlanders. We passed around Dear Dairy ice cream and a few leftover sweets from Sodt. Fireworks cracked somewhere behind the trees. We didn’t even bother turning around.

No sparkler could’ve topped it.

Day Two: Lobsters + Vintage Fire Trucks

We woke up wrecked and caffeine-starved and ran straight to Tandem. The line wrapped around the building. Honestly, I thought about bailing. But we hadn’t seen each other in months, and standing in the sun half-asleep with people you love beats most things.

They each took one bite of their breakfast sandwich and said the same thing: “Best I’ve ever had.” I just smiled. Portland does breakfast sandwiches better than most cities do dinner. (And yes, they already had the list.)

They were craving lobster, so we packed the car and headed north toward Five Islands. On the way, we pulled off in Bath for another coffee at Solo Pane and stumbled straight into the Bath Heritage Days festival.

Next thing we knew, we were at the Fireman’s Muster, being handed a hose and told to help pump an antique fire truck, as if we knew what we were doing. My arms still hurt.

We made it to Five Islands Lobster Company late afternoon. Ordered the biggest lobster rolls on the menu. Watched boats bob around like they had nowhere better to be. Exhausted, we decided to stay the night.

Might’ve been the views. Might’ve been the biceps.

Day Three: Beer, Butter Chicken, and Horseflies

We rolled back into Portland that morning, already sweating. It was pushing 96° and climbing, so we ducked into Washington St. to check out Sissle & Daughter and Onggi. We made it about fifteen minutes before the heat chased us out.

We bailed and drove to Freeport. The Maine Beer Company is only fifteen minutes away, ice-cold, and one of their favorite beers. We ordered a flight and sat inside just long enough to cool down and feel like humans again.

After that, I leaned all the way into the tourist energy. Took them to one of my favorite classic moves: a walk around Portland Head Light. Still hits. We did the full loop, took the same photos everyone else does, and stood in silence for longer than expected. Some views just don’t wear out.

Dinner was at Taj in South Portland. None of us had been before, and now we’re all fans. Indian food in Maine can be hit or miss, but this place got everything right. Deep flavor, perfect heat, big portions, and a price that didn’t make us blink. And yes, we got the butter chicken. You would’ve too.

We ended the trip at Red’s for ice cream. Got completely eaten alive by horseflies in the parking lot, but the soft serve were worth it.

That was our 72 hours. No schedule. No strategy. Just three hot, happy days with people I love.

At one point, standing by the harbor, my sister said, “I get why you live here.” She didn’t say much else. She didn’t have to.

If someone came to visit you, where would you take them?

Tell me. Or better yet, send them this.

Before The Logbook existed, I emailed Portland Food Map to see if they were hiring. That’s how much I loved it. Still do.

It’s the first thing I send to anyone moving here. It’s where I go when I want to know what’s actually happening, not the PR version, the real stuff. Pop-ups. Openings. One-night dinners you’ll regret missing.

If you already check it weekly, you get it. If you don’t, this is your sign.

The Portland Food Map: Upcoming Food and Dining Events

🐾 Adoptable Buddies of the Week! 🐾

🐶 Jackson – 3 years old, 86 lbs
Strong, goofy, and full of love. Jackson needs an active, adult-only home where he can be the center of attention and keep learning the ropes.

🐱 Fluff Nugget – 5 years old
Shy at first, but sweet once she settles in. She’s quiet, gentle, and would love a calm home where she can take her time.

🐕 Interested? Check them out here

🏚️ For Sale This Week (Because It’s Too Cool Not to Share)

19 Arbor Street – Engine House No. 9

Built in 1902. Used to house fire trucks. Now? Hard to say. It’s tucked behind Forest Ave like it’s hiding in plain sight. Red brick. Arched bay doors. Slate roof still holding strong. The thing’s massive.

8,300 square feet. Three city lots. Enough warehouse energy to make you wonder what you’d even do with all that space. It was renovated back in 2009 but not in a way that erased the good stuff.

Feels like the kind of place you throw a party no one forgets. Or open something weird and cool. Or maybe just live out your firehouse fantasy with room for all your projects and then some.