How to Plan a Last-Minute Getaway with a Toddler

After double-checking the math, I had two free nights available at Marriott with all of our points...and only a month to use them. Let's goooooo!

Dec 20, 2024

You’re reading this newsletter because I’m a big travel planner. I always have a trip planned, 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…if anyone has suggestions on this, please please leave a comment!

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. Three people who can help you if you want to get into it, though:

The Points Guy is one of the OG travel bloggers, he built his whole business on maximizing points.
Geobreeze Travel runs a great podcast that is all about points.
This beginner guide from NerdWallet is a good overview if you’re just getting started.

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.

This week’s rapid-fire recs

Disclosure: This newsletter contains affiliate links, meaning I get a commission if you decide to make a purchase through my links, at no cost to you. I promise I’ll only ever recommend products I’ve actually used and loved.

It’s “best places to go in 2025” season! This list from CNT is getting those juices flowing…
Still deciding, but I think under the tree for my toddler this year will be this Encanto-themed sticker book, a mini-Duplo set, this play tent, and the Slumberpod since we’re having a biiiiit of a tough time fitting into the pack n’ play. (How is it so soon!!)
We’re big Ms. Rachel fans in this house. This article was a fascinating look into the toddler phenom-to-toy pipeline in time for the holiday season. (NYT Gift Link)
Highly recommend the Yolo Intel travel substack. This issue has a great section on traveling with babies.
Haha, too real.

If you want to recreate our last-minute Portland getaway…

This is an abbreviated version of my Portland destination guide, which will go out to paid subscribers next month. If you haven’t already, consider supporting Travel with Toddlers with a paid subscription.

Okay, on to the getaway stuff.

Trip strategy and itinerary:

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, and wishing I had bought a ticket in time for the Polar Express.
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., ZU, Norimoto, Tandem Coffee and Bakery, and BLVL.
Reading out loud at two of my favorite bookstores, Longfellow and Print.
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.
Sampling multiple cuisines at the Pine Street Market (my favorite is Mr. Tuna’s sushi rolls.)
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 and the Portland Art Museum, but I love the latter and can’t wait for my toddler to be old enough to go for First Fridays, where the whole street closes for the evening for vendors, musicians, and artists to gather.

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.

Cramming in a last-minute trip right at the start of the holiday season was not on my list this year but I’m glad we did it. It was the reset I needed as we rush into the flurry of baking cookies and decorating the tree and late-night lights and too many nights of pushing bedtime/sugary snacks in a row, ending in family-wide meltdowns.

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 a holiday season with the good kind of surprises, and lots of love and light and joy this season.

Cheers,

Kayla