You’re reading this article because I’m a big travel planner. I always, always, always have a something on the calendar, even if it’s small, even if I’m bringing my little one. But because planning brings me joy, I’m not usually a fan of the last-minute trip. I have a whole pre-trip ritual that starts with a ridiculous amount of laundry, several side trips to Target for fun snacks/surprises, and a lot of toddler prepping/talking about where we’re going and what we’ll do.
This trip I did none of that.
And would you look at that, it went great anyway! I’m honestly so proud of our ‘lil family for it all going smoothly, because that was NOT my expectation, so instead it was a sweet surprise. The only major speedbump is that our very lanky toddler has now officially grown out of the pack n’ play so we had to McGyver a Queen bed setup…yes, we just ordered the Slumberpod for next time.
How the last-minute trip happened
I’m late to the game on the points-maximizing side of travel, mostly because I’ve never really been able to make it work with vacation time and destinations and school breaks lining up. But now that we have a toddler (and my husband travels for work more often), we suddenly have points!
I’ll be the first to admit I don’t know that much about the points game. It’s a little too Moneyball for me, if I’m being honest. FamilyVacationist has a ton of resources on this, including this guide for booking all-inclusives with reward points, which I just bookmarked myself for spring break.
Anyway, I’m not used to planning trips around points, but when I figured out we had two free nights at Marriott that we hadn’t used this summer (whoops), I booked a super last-minute trip to Portland, ME…and we had the best time!
A view of the iconic Portland Head Light.
Map out a rhythm, not a plan.
Coming off the heels of a super highly planned Disney trip (where I wasn’t even the primary planner – thanks Mom!), a weekend getaway with nothing major planned felt really…nice.
We got to Portland with only a rough sketch of a plan and the name of our hotel—the AC Hotel Portland Downtown/Waterfront on Commercial Street—which I vaguely knew was on the edge of Old Port, but not much else. I’ve been to Portland a gajillion times because it’s the cutest city ever (and the closest city to my alma mater, 1.5 hours away) so I kinda know my way around and there’s no real push to do anything new. Instead, I focused on the typical rhythm we do every day with my toddler:
- 7:00 AM: Breakfast
- 8:00 AM Playtime
- 9:00 AM Outing
- 11:00 AM Lunch
- 1ish PM Naptime
- Wakeup: Playtime
- 5:00 PM Dinner
- Last wiggles out, bathtime, bedtime routine
- 7:00 PM Lights Out
This may seem like Too Much, but it’s what’s worked after a lot of trial and error with my toddler. We *need* a schedule and I use that royal we very intentionally. I really need structure and routine (and I get so hangry that the eating times are non-negotiable anyway…kinda like my toddler. Wonder where they got it from?)
With toddlers, you need to travel with a clear intention.
Before kids, I used to do ALL THE THINGS when we traveled. Eat the best food, see the best art, get tickets to a show, workout in the mornings, take a day trip somewhere far away, whatever it is that’s available, I would do it, even for destinations I’ve been to before.
With a toddler, I try to think about my trip way more intentionally. Right now, trips tend to fall into two categories:
- Parenting in another place
- Relaxation/sunshine
Most of our trips are some sort of balance. I dream of Paris, of Florence, the art-drenched museums and lingering lunches and long wandering walks through gorgeous foreign cities…but that is not the current phase of my life. For a last-minute trip like this, I went with “parenting in another place,” which meant: Playground hopping, outdoors time, and sticking to our schedule as much as possible.
No, I did not get hit in the face while taking this picture, but it was a close call.
Doing this meant even though we were parenting in another place, we had a LOT more fun. I think we spent almost 5 hours total across the weekend at the same playground and y’know what? It’s a great playground. We play this game on the curvy slide where my husband and I take turns running and jumping into view while my toddler slides down and the giggles, I am telling you, were the kind of giggles that echoed across the bay and made everyone in the park smile.
If you want to recreate our last-minute Portland getaway…
Portland is such a wonderful little city. We did just a weekend, but you could easily use it as a home base for 5-7 days if you wanted to, especially in the summer months when the beach is calling. I’m going to focus on just the two days here, but the full destination guide will have more extras.
Where to stay:
In the off-season, I’d definitely recommend staying downtown in Old Port, like we did at the AC Marriott. During the busy summer months though, these can be hard to come by. Renting an Airbnb in nearby Falmouth, Cape Elizabeth, or Portland’s sleepier East End or West End could be a better bet. (Portland is super walkable, so you’d be more of a stroller walk away from downtown but closer to good playgrounds.)
Where to go:
Peak’s Island is about a 20-minute ferry ride from Old Port and is super cute.
It’s cold in Maine, but that didn’t stop us from having a great time wandering around the city. You can use Portland as a stopping point for slightly more touristy spots (farther North: Freeport, Downeast, Acadia; farther South: Kennebunk/Ogunquit, Portsmouth) but we enjoyed what the city had to offer:
- Stroller walks along the ME Narrow Gauge Rail Trail. If you can get a ticket to ride on it, my train-obsessed toddler loved that outing.
- Swinging at the top of Eastern Promenade Playground with gorgeous views of the Bay.
- Taking allllll the bakery breaks at Holy Donut, Standard Baking Co., Tandem Coffee and Bakery, and BLVL.
- Reading out loud at two of my favorite bookstores, Longfellow and Print.
- Visiting the Portland Art Museum which is a quick contemporary art museum that had lots of open spaces and some very cool artifacts (like an entire birch bark canoe!) that is great for slightly older toddlers.
- Riding a ferry to Peak’s Island, where we rented bikes, played on the beach, and wished Il Leone pizza was still open for the season.
- We skipped visiting touristy stuff like the Portland Head Light but it’s one of my favorite spots, and definitely a must-do, especially if you go to one of the beaches nearby like Willard Beach or Crescent Beach State Park.
- We also skipped the Children’s Museum but I’ve heard great things. We ran out of time and if I’m being honest, I dislike going to children’s museums! We had so much fun at the art museum, there’s no need for overstimulation, imo.
Where to eat:
Portland has better food than any other city in New England (maayyyybe Burlington comes close.) You can expect super high-quality food with local ingredients pretty much everywhere you go, and I’ve never had a bad meal here. Be warned, though: Some of the seafood places don’t have much beyond seafood. My top two spots for happy hour, Island Creek Oysters and Hunt & Alpine, don’t have super kid-friendly menus. (They’re worth packing a little something and/or going during naptime, though.)
I always recommend going to Washington Ave for BBQ/tacos at Terlingua or garlic noodles at Cong tu Bot. We did brunch at the Friendly Toast with about a thousand other toddler families and it was delicious. Portland also has an awesome brewery scene if you’re into that which can be fun for kiddos too, but I’m not a big drinker so the only brewery I like is Oxbow because they have the Duck Fat Frite Shack outside.
This Eater list is solid if you’ve never been and really want a lobster roll (my favorite lobster roll is at Harraseekett Lunch and Lobster in Freeport, no offense to Luke’s or Eventide.)
Thanks for being here.
A little beach time with friends in Georgetown, ME, about an hour downeast of Portland.
Traveling with my toddler has continued to surprise me—for example, at Peak’s I thought the golf carts would still be available in the off-season (of course they weren’t, idk why I thought that) so all the hyping up about the golf cart ride would end in tears. Instead our toddler was cool with riding in a bike trailer, which they’ve never done before, wearing a helmet and all kinds of uncomfortable layers. Suddenly we’re go with the flow? I’ll take it, I’ll take it!
All this to say, I hope on your next trip your kids surprise you in this way. I get stuck sometimes with a set idea of what my kid was like in the last phase, not the phase they’re in. Every time they grow up a little I’m always caught off guard, even if it’s as small as letting me put gloves on them instead of fighting it.
Here’s to wearing all the layers and going outside anyway,
Kayla
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This post was originally published on Travel with Toddlers. Subscribe for more real-talk travel advice, toddler-friendly itineraries, and tried-and-true gear recommendations.
