They say you get almost as much joy from planning a trip as you do from the actual experience of the trip, and at least for me, that’s very true. (I mean, I did work at Tripadvisor, after all!) Deep research on itineraries, cuisines, cultural practices, history…it’s part of what I love about traveling, honestly, because it’s a chance to learn about a place you’ve never been.
With a toddler, though, there’s a whole second dimension to this research, that’s driven just as much by anxiety as it is by joy. Will there be bathrooms close by the pool area? Is our stroller going to fit down the hotel hallway? Does the restaurant have 5pm reservations available?
On top of that, there’s so much more pressure than before to get it right. I used to travel all the time and the mishaps were very much part of the adventure. Wrong turn? Let’s stop at this roadside stand for pastries! No raincoat? An excuse to go shopping. Now, though…if I whiff on an itinerary, the Mom guilt really gets going. It’s my job to make sure we all have a good time (including me!) and so yeah, no pressure, but I’ve never been here before either!
Enter: Lots and lots of research. Definitely more research than I would do for a trip for myself, and that’s saying something. Today I thought I’d bring you along on this (slightly unhinged) process so you can see what goes into planning a great, toddler-friendly trip…even if I’ve never been there before.
How I research places I’ve never been.
My SECOND time in NYC total, as a recent college grad. A blast!!
We’ve booked a trip to New York City to see Paddington on Broadway (!!!) this spring—and while I have, technically, been to New York before, I’m very much a tourist there. I think I’ve been maybe three or four times? I’m a country mouse, what can I say. I’ve also never been with kids and so I’m taking a more conservative approach to what I think I know about the city.
Below is my step-by-step process using New York City as an example:
1. Start with traditional media.
I think there’s a temptation to jump straight into social media for recommendations but WAIT! If I’ve never actually been to a place before, my first stop is my local library. Maybe this is just the liberal arts grad in me, but I want to know the full context of a place before I dig into the specifics, and so I start with traditional, old-school guidebooks (Fodor’s is my go-to for this) because they actually explain the different neighborhoods, the overall feel of a place, and can help me get oriented, so to speak, on what’s important and what’s extra about a given destination. I usually read this alongside a map so I can literally understand, okay, that’s 30 minutes away from this, or this area I thought would be part of our trip is actually a day trip away from the city. Did you know it takes, like, 45 minutes to get from Manhattan to Brooklyn??
I’m not filtering yet by family-friendly so much as trying to understand what makes this place special. What are the iconic aspects of the place we have to do?
From there, I go for legacy media properties: The NYT 36 hours, The Eater 38, browsing magazines like Conde Nast Traveler and Travel and Leisure and of course, here on FamilyVacationist. I want to know where travel writers go when they go to New York. What hidden gems am I missing? What restaurants are worth remembering? What is worth it, and what is hype? Those pubs will tell me, generally. (Though sometimes there’s a level of luxury there, funded by the magazines or properties, that is unrealistic.)
MAKE MEMORIES: America’s best family vacation spots, vetted by real travelers and families: FamilyVacationist’s 2026 guide
The point is patterns. I’m not necessarily going to do every touristy thing everybody recommends doing, but if I know what’s on every list, I can see what I feel like I need to check off to see a place vs. what would be cool to do vs. what I want to avoid because it’s too crowded. For example, the first time I ever went to New York we did a whole day at Ellis Island and the Statue of Liberty—my family immigrated through Ellis Island several generations ago, so that was a special must-do. I might not do this with a toddler, but I do know it’s something I’d like to do with them someday to teach our family history, too.
2. Then I build a mood board on Pinterest for the ~vibes~
My NYC mood board – full of little kid fun, good food, and lots of wonder. All images from Pinterest.
I am a mood board person, and I often build one for an upcoming trip. This is more about curating vibes and less about specifics. How do I want the trip to feel? This might be informed by iconic films or songs or just what I imagine a place to be. I’m going for what makes me say, Yes! This!
For New York City, because it’s so embedded in the American ethos, I already know any trip I go there needs to have the subway, a slice, a really good bagel, a bookstore.
For the mood board images, I add the word “aesthetic” to my searches. Once I’ve got a mood board vibing, I dive into the more useful side of Pinterest, where I start looking at what bloggers recommend for New York City. This is also where I go back and search specific bloggers I’ve loved for years—Jess from Where is Briggs, Jessica Wright from Bon Traveler, Carly Riordan to name a few—to see if they have itineraries or tips they’ve posted in the past. They all have little ones now so that’s a bonus.
The thing about these kinds of listicles on Pinterest is they often overindex on children’s museums and kid’s spaces, which is totally fine! But I’m not interested in spending time in a brand new place just for a children’s museum. I’m looking for places that are unique to that destination and that really have something to offer. The children’s museum, unless it’s particularly special, is more of a back-up, it’s raining and we can’t playground it out thing to add to the itinerary.
4. Once I feel confident, I choose our home base neighborhood and hotel.
This is the most important decision of the whole itinerary. When I choose a property, I’m generally looking for:
- Proximity: How close is it to some of the big-ticket itinerary anchors I know we’re going to want to do. I mentioned we bought tickets to Paddington on Broadway, which is our major event that we’re going to New York City for. Obviously, I don’t want to stay in Times Square (I’m a tourist, but not THAT much of a tourist) but I’m equally not going to choose a Brooklyn hotel for this particular trip. We’re going to be mostly in Manhattan since we’re only staying a few days.
- Amenities: Not every hotel really caters to families, so making sure they have some basics, which usually requires calling to confirm. Sometimes, also, there’s other issues like construction or closures. For New York, I’m less worried about this since there are restaurants everywhere, but after accidentally choosing a property once with their restaurant closed for renovations in a more rural area, I always call to double check. I also try to find a place with a pool—it’s a built-in way to blow off steam after quiet time.
- Points: Finally, I cut all of this by whether or not we have points/status at that particular hotel. Is every Marriott something to write home about? No, probably not, but when you can stay for basically a night free by cashing in points, that’s where we’re going to go. Last time I visited the city it was for my anniversary and we splurged via points on the St. Regis, which was steps from Central Park and the MoMa, and absolutely perfect for a quick 24 hours in the city.
5. Then I pick one neighborhood per day to explore, with one “hero” activity per day max.
For this trip, we’re staying in Midtown Manhattan—I know, I know, it’s the tourist version of New York. Again, it’s all about proximity!
Once I have our home base, I build day-to-day itinerary based on what’s realistic and what neighborhoods we want to explore. Ideally, where we are staying is the highest concentration of stuff we want to do, but I think of a trip in blocks like:
- Day 1, Home Base: Midtown
- Day 2, Exploring Nearby + “Hero” Activity: Central Park + Broadway Matinee
- Day 3, “Hero” Activity/Exploring a Different Neighborhood: Brooklyn Bridge and Pizza Crawl
That’s just an example, but you get the idea. Each day is a different spot, but we’re not going to try to jump around between spots. We’ll take the subway at least once and a taxi at least once for my transportation-obsessed toddler which is it’s own activity, too.
To find these “hero” activities—aka, the ONE thing we are doing each day and the rest of the day is downtime/bonus/a playground—I use the above media I’ve already mentioned, plus I do a lot of rooting around Substack for deep-dive itineraries that people post. At this point, I really am explicitly filtering for toddler-friendly activities, or at least articles from people with small children. For example, you can’t do a Broadway show with a baby—they won’t let them in the theater! That’s something I wouldn’t have thought of without doing some of this research.
For example, Christine Amorose Merrill wrote a great overview of NYC with littles. The last time I visited I was blissfully kid-free and the times before that I was just out of college, so this kind of intel is VITAL.
Finally, and I do this last on purpose: Instagram and TikTok. This is where I go for deep-dives to confirm my choices. Okay, now that I’ve chosen, say, the Natural History Museum, can I find content from someone with a toddler to see what it’s actually like? Literally seeing it can be super helpful, and seriously, those of you who do this kind of work—thank you, from a Mom who just doesn’t want to wonder if there’s going to be a run for the potty because there’s only one bathroom at the entrance.
Normally, I really wouldn’t do this because I hate to “spoil” a destination by knowing too much. But for Mom stuff? Playgrounds, reviews of specific experiences like a high tea with little ones, museum overviews, all that stuff is so useful when you’re on the ground so you don’t feel disoriented. My attention is already split between navigating around a new space and keeping my kid happy that I need something to hold on to.
The final itinerary with a toddler is never super rigid. I make sure there is quiet time built in every day, plus some room for spontaneity. (I literally put a block in that says: “Spontaneous exploration”—listen, the Type A thing only goes so far.) I usually write down every single restaurant or bakery I’m interested in, for example, in the neighborhoods we’re going to be in, so if we pass it while we are hungry I know where to stop, but don’t worry if the line is too long or we’re just not into it at that moment.
Then, I prep the toddler.
As we get closer to a trip, I also do a library run for books themed around the place or the activities we’re doing. Since we’re doing the Paddington show, we’ll probably keep those books in our reading rotation, and then add in classic NYC books like Eloise and The House on 88th Street, plus a few more general city books like Last Stop on Market Street and The Ultimate Book of Cities. This helps provide context and explain a little bit about our trip, so I can start cueing that we’re going somewhere.
Finally, a few days before our trip, we have a family meeting where we present the itinerary and discuss so they can ask questions. When they’re older, we’ll do this much earlier in the process so they can offer input and do their own research! But for now, they’re mostly along for the ride. I may offer some age-appropriate choices for this trip, like choosing between two playgrounds based on the pictures, for example.
Thanks for being here.
Yes I went to DUMBO specifically for a viral dessert and this Instagram shot. It was 2015, okay? I unironically posted this with Taylor Swift’s “Welcome to New York” lyrics as a caption. Millennial cringe is real!
Phewwwww that’s a LOT but it’s not all at once, and there’s lots of joy in this! I’m not saying you have to do it this way, just that this is how my brain works. I find studying a place to be fascinating. I love art, architecture, and history, and so a lot of this research is to tickle my own brain, especially if I’m not going to be able to take a proper tour while we’re there.
I’m personally hoping to sneak some time for myself at the MET if I can, maybe during quiet time, and honestly, I’ll be happy with a really, really good slice of pizza. I visited Scarr’s Pizza in LES after a Bon Appetit recommendation a few years ago and I’m still thinking about it…
Neeeeewwwwww Yooooooork, concrete jungle where dreams are made of,
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.
