Let me be upfront about something. If you’re looking for a color-coded, hour-by-hour itinerary with perfectly timed bathroom breaks and zero meltdowns — this is not that. When I put together an itinerary, I plan by the day, not by the hour. I have a list of things I want to see and do, we pick what makes sense when we wake up, and we go from there. With kids, that’s really the only way. They can be perfectly happy one minute and absolutely beside themselves hungry the next — and no amount of planning fixes that. What fixes that is Uncrustables in the car at all times.

Seriously. We can collectively eat a dozen in under 30 minutes. They require zero prep, they travel perfectly, and they have saved more than one trip from a complete meltdown spiral. Stock the car. You’re welcome.

With that said — here’s how our August 2021 Maine trip actually went, along with my suggestions if you’re planning your own. This was our first real trip after the pandemic. The world was just starting to open back up and honestly, there was a weird anxious feeling about it. Like, are we really doing this again? But we did. And it was worth every second.

Getting There

We flew into Portland. I booked our hotel on points — tickets were pricier than I wanted, so I saved where I could. That’s always the game. You spend a little more in one place, you find it somewhere else.

Now. Car rentals. August 2021 was not a great time to rent a car. The inventory was basically nonexistent and prices were out of control. This is actually how I first came across Turo — I had booked something through them without really knowing much about the platform. I kept looking around though, and eventually found a small SUV through a traditional rental. Canceled the Turo with no issues. But I filed that one away for future trips.

Portland — Lighthouses, Lobster, and Aggressive Seagulls

We spent a day exploring Portland and the surrounding area, and lighthouses were on the list. Portland Head Light is the most photographed lighthouse in Maine and once you see it in person you completely understand why. It sits inside Fort Williams Park — free to visit, just pay for parking — and there’s history all around you. The old fort structures are worth walking through and the rocky beach access is a nice bonus. It’s one of those spots where you just stand there for a minute and take it in.

From there we made our way to the Lobster Shack at Two Lights for the most Maine meal you can possibly have. Lobster outside, water in front of you, wind off the coast, rocks everywhere. Incredible. The view is beautiful and the food is even better. The only thing standing between you and a perfect meal is the seagulls — and I cannot stress this enough, they are bold. They have no fear. They will look you dead in the eye and go for it. Hold your food, watch your plate, and enjoy every second of it anyway because it is absolutely worth it.

Acadia National Park

Three hour drive from Portland and completely worth it. Acadia is stunning — and I’ll say this, they do accessibility pretty well for a national park. There are areas that just aren’t possible for Matt with his walker, and he is the first person to tell us to go ahead and not miss out on things because of him. So there were moments where he sat at the top and watched us scramble down the rocks while he had arguably the better view.

We love the drive-and-park-and-just-look approach to national parks. Pull over, take it in, eat an Uncrustable, keep going. The boys loved jumping rocks and exploring the coastline. Just be prepared for the seagulls because those birds have zero boundaries at Acadia either. Apparently it’s just a Maine thing.

White Mountain National Forest, New Hampshire

We added a day trip to White Mountain National Forest in New Hampshire and going back in the fall for the leaf colors is now fully on my list. We honestly had no idea what to expect — we figured we’d just drive and see what we found. We pulled over where we saw other cars and stumbled onto a beautiful stream lined with huge rocks.

The boys had their swim trunks and made the most of every second of it. They waded and splashed in that stream for hours while Matt found a good spot nearby to sit and take it all in. One direction there was a whole crowd of people, but we were far enough away that we had our own little corner of it. And if you angled yourself just right — and casually nudged the kids a few feet to the left — you could get a photo that looked like you had the whole place to yourselves. Highly recommend this photography strategy.

That’s the thing about loose itineraries. We pulled over on a whim and it turned into one of the best moments of the whole trip.

Boston Day Trip

I had been to Boston for a work conference a few years back and fell completely in love. I knew I had to bring the boys. So we made it a day trip — and honestly, I mostly just wanted them to ride the duck boats. The history, the cannolis, walking through the park. It’s only a couple of hours from Portland and the contrast is wild. You go from this quiet, rocky, outdoor Maine vibe to the full energy of a city in just a few hours. Both incredible, just completely different. Boston is one of those cities that gets you. We’ll be back.

The At-a-Glance Itinerary

This is how I do it — suggestions for each day, not a schedule. Pick what sounds good, skip what doesn’t, and leave room for the stream you didn’t know existed.

Day 1 — Travel Day. Fly into Portland, late arrival, get car, check into hotel. Nobody needs to be a hero on travel day. Get there, get sleep.

Day 2 — Portland. Explore downtown. Portland Head Light and Fort Williams are a must. Holy Donut, while you’re at it. End the day at Lobster Shack at Two Lights — and watch your plate.

Day 3 — Acadia National Park. Three hour drive, worth every minute. Plan for a full day. Bring snacks. Bring Uncrustables. Watch your food around the seagulls.

Day 4 — New Hampshire / White Mountains. Drive through White Mountain National Forest. Pull over when you see other cars. Pack the swim trunks. Let the kids find a stream and just go with it.

Day 5 — Boston Day Trip. Two hours south. Duck boats, cannolis, the Freedom Trail, walk the park. One day is enough to fall in love.

The whole trip was outdoors, which is exactly how we like it. Maine has this way of making you feel like you found something most people drive right past. And when you pair it with the chaos of kids who are thrilled one minute and dramatically starving the next — it just makes for the best kind of trip.

Pack the Uncrustables. Leave the rigid schedule at home. The best stuff usually happens when you pull over and see what’s there.