Shortly after giving birth in May, I was riding a no-longer-pregnant, feeling-instantly-great, didn’t-even-need-stitches-this-time, I-can-do-anything high and believed it would be fun to book a trip to New York City with my husband and three small small children. I have visited NYC only once, when I was pregnant with my first. My craving to visit this time stemmed, I think, from a) having been invited to the wedding of a dear old friend in the city early this summer but being rendered unable to go by, as I mentioned earlier, giving birth, and b) finally watching all of Girls earlier this year. I knew a kid-free trip wouldn’t be in the cards, since I would be breastfeeding, so we decided to try it with all three kids (ages five, almost-three, and five months). Here are 21 thoughts about the experience.
How we traveled: 4-hour direct flight to Newark Airport (the cheapest option), bus to train station (bus skipped our stop so we enjoyed a long stroll through Newark to get to the right station), subway to the city, then walk to our Airbnb. We did it all in reverse on the way home, which admittedly stressed me out, since there were just so many transitions at which we could have grossly miscalculated where to go and how long it would take. And missing a flight with three kids in tow would have been nightmarish. (We made it in the nick of time.)
I knew toting our stuff was going to be tricky, since we were a group of five travelers, only two of whom could carry any luggage and who would also have to carry some of the other travelers. We packed everything in three carry-ons and a personal item (I was proud of this). My husband wore an Osprey backpack and pushed the stroller with my duffel bag stuffed underneath, while I wore the baby in my Tula carrier and pushed a rolling suitcase with my Olend crossbody bag tied on the handle. This worked as well as it could have!
A note on our gear: We took our Mockingbird stroller (which we usually use as a double stroller, but configured with just one seat for this trip) and purchased the riding board attachment especially for this occasion. I was hoping my five-year-old would walk as much as she could and then we’d have the riding board option for when she got tired, but it turned out the board was just too fun to resist—she preferred to ride it pretty much the whole time. Which was fine—it was actually mostly convenient, and we got a lot further with it than we would have if we’d had to verbally motivate her to walk when she didn’t want to. We covered a good 25,000-ish steps each day. (There was a lot more conflict than I’d expected over which child got to use the riding board and which got to sit in the main stroller seat, though I really don’t know why I didn’t expect that.)
We did walk a LOT, and usually opted to walk rather than take a subway, because a) walking is the best way to experience a new place, and b) most subway stations are not very wheel-friendly! Almost every time we took the subway we ended up unloading the kids and letting them walk while my husband and I carried the stroller down the stairs. It was a hassle, but not enormously taxing (though I have to wonder how those who really *can’t* get up and walk down stairs navigate the city??). Running through subway stations was almost certainly my middle child’s favorite part of the trip.
Speaking of subway stations: New Yorkers seem to have a reputation for unfriendliness, but in our experience there was someone right there at every station offering to help us with the whole stroller production—we never had to ask, or even wait a single moment. On one memorable occasion, a commuter saw us approaching the subway turnstile and used her card to swipe me in so I could open the accessible door from the other side and let the rest of the family in—except that the door would not open. Probably six different people stopped and tried their best to ram it open with their bodies before giving up and walking away with apologies. One man was in the middle of helping my husband loft the stroller overhead to get through the turnstile when lucky New Yorker number seven came by and kicked the door handle with all his might, which finally did the trick.
It was both harder than and exactly as hard as I expected? I have been known to say that the kids are actually at their best when we’re on the go. It’s when we stay home that the worst usually comes out. And yet I knew the trip would ask a lot of them: to sleep in a new place, to adjust to a new time zone, to take in constant stimulation and a disruption to the routine and enter spaces where they needed to behave themselves. Most of these things they actually did remarkably well. Their interactions with each other were perhaps more strained than usual, mostly due to conflicts over who got to sit in which stroller seat. Traveling in such close proximity to each other—always just an arm’s length away—allowed for plenty of opportunities to physically bother each other. And those short moments at the beginning of each day when we were all trying to get ready for the day in a pair of tiny rooms were some of the roughest.
Since anticipation is half the fun of any trip, we did our best to really hype up the sights and experiences on offer in New York City, especially for our five-year-old. I rented library books about famous artworks we’d be seeing in person, we watched vlogs about restaurants and stores we could visit, we studied notable tall buildings. She seemed appropriately eager for all this. It was somewhat deflating, then, when we arrived and began pointing out the things we’d been mutually excited about— “Look, it’s Times Square! It’s the Empire State Building!”—only to get an irritated, nonverbal response equivalent to “I’m tired, I don’t care.” It just seems like for a five year old, who has no context of the scope of the planet and no sense of past, present, or future, it is difficult to appreciate the contrast between a bustling metropolis and our own textureless suburb 2000 miles away. Perhaps daily life is still sufficiently novel for her that a drastic change of setting barely registers.
The one thing she had seemed more excited to see than anything, though, was the art. I admit I’ve encouraged her enthusiasm about this. But I encourage her to be enthusiastic about a lot of things she just doesn’t care about (thrifting, beets, speaking kindly to her sister)—she isn’t afraid to disappoint me. I began to worry that her interest in the paintings would wither when faced with the reality of an art museum: canvases on a wall in a quiet room. It was beautifully affirming, then, to experience the museums with her (first the Whitney, then the Met), and see the excitement come out in full force. At the Whitney she’d precede me into each room, then come back to beckon me on, eagerly pointing out works she recognized—Georgia O’Keefe’s Summer Days, Lee Krasner’s Spring. When we’d been there close to two hours and I was feeling the judgment of my fellow visitors (maybe imaginary?) for bringing a restless three-year-old through the museum, I said it was time to leave; she was confused, expecting we would explore every floor of the museum. At the Met she fangirled over Matisses and Frankenthalers. She saw a line of people waiting to take a selfie with a Van Gogh self-portrait; not eager to wait, she wanted to take a selfie instead with The Potato Peeler on the reverse of the canvas. She had been promised we’d see some Mary Cassatts in the Met, but the rooms were closed for renovation; we went on a wild hunt, carrying the stroller down multiple staircases, to an uncrowded labyrinthine room, finally locating a couple of Cassatts on tightly-packed shelves. Then we were allowed to leave for dinner. Its’s very fun to me that she’s a child who does not need to be convinced of the value of looking at art in person.I’m proud of the five different outfits I put together with only six items, since I only had the space of half a carry-on for my own wardrobe. Sadly it was too warm to actually wear most of them as planned. (Weather was about 70 and sunny every day, which is literally perfect and hard to complain about, except for the fact that I wanted more of a true Fall in New York vibe.) This is a good capsule I’ll remember if I ever need to pack light for a colder weather trip.
It’s always wild to me how I can go on a city trip and eat like absolute crap for every meal with no regard to my vegetable or protein intake and yet feel unprecedentedly great, I presume because I’m walking constantly? It made me think, hey, I could walk all day at home, I could walk to the grocery store with the double stroller every other day instead of toting a multimillion-dollar Costco haul (slight exaggeration!) in my minivan. Except that the walk to my nearest grocery store isn’t cute. The vibes are unpleasant. Which is unfortunate. Walking is just so important to me.
Which leads us to the classic question every good traveler must always ask whenever they go on vacation anywhere—Should we live here?? Of course we discussed it. For several reasons I think our answer has to be no, I don’t really think New York City is the place for us, even if it was financially feasible. But more generally, we have been pondering the question of whether we ought to be living in a city. There is a part of me that believes I am meant for city life. It would of course come with many tradeoffs, especially for a family with multiple children. But it’s hard not to feel life my would be in some way improved if I lived in a cultural hub. I walk into a Brooklyn bookstore where I’m flipping through exciting used art books and listening to Pulp’s “Babies” which has just come on the speaker and it’s hard not to think I belong here, why is my only bookstore option a strip mall Barnes and Noble, there are so many books you can’t find at Barnes and Noble! I walk through the Met with my daughter, clearly a budding art critic or historian or something, and think, we could see a Matisse every day of our lives with free-for-New-York-residents admission! But it also seems a little silly to think my quality of life would be significantly improved by living near a used bookstore that plays my favorite songs. Or does it? Why do people like the places they live? What does it come down to? I’m worried I’m just drawn to vibes—but what is a vibe worth? What if I moved to New York City and never actually went to the Met, because the reality is I’m a mom of three children, and it really actually just makes a lot more sense for me to do weekly Costco hauls in a minivan, and that is quality of life? I don’t know.
I had kept my expectations for this trip low. Still, I watched a lot of Chantal Wirekoh’s lovely YouTube vlogs (which I think I will continue to watch even post-trip purely for the atmosphere), as well as other TikTok vlogs, which instilled in me a vision of certain activities I was casually devoted to squeezing in. One of these: having a glass of wine in a plastic cup while I watched my children play in Central Park. Another: trying an espresso martini while seated outdoors at a cafe. Instead, I had not one adult beverage on this trip. I just never found myself sitting around thinking, you know, being a little tipsy right now would enhance this experience. Or, hey, you know what I’d really like to do? I’d like to stay in this restaurant slightly longer than is strictly necessary.
I find that opportunities to dine in general are significantly curtailed when traveling with children. Often, you have ideas of where you’d like to eat, but when dinnertime—or bedtime—approaches, you don’t have time to travel and potentially wait for a table. Sometimes the only thing to eat is the closest and fastest thing. We did have several good bagels, and several good pizza slices. Our best meal may just have been a jumble of meat and rice from a halal cart, scarfed from a styrofoam tray at the famous Bill Johnson playground (which really was lovely). I am legitimately proud of how well behaved my children usually are in restaurants, and I don’t even give them iPads! Still, they have their limits; dining as an experience is not especially likely to happen. In fact: my daughter chose as her first souvenir a handpainted notebook from McNally Jackson and took to writing a bulleted list of everything we’d done each day of the trip. On our second morning, as she went to update the list for the previous day, she asked me, “Where did we eat dinner yesterday?” “We didn’t really eat dinner yesterday,” I said. We’d eaten lunch at 4 pm (Prince Street Pizza in the Elizabeth Street garden in Soho—highly recommend!) and then shared a salted caramel milkshake between the four of us. She seemed scandalized, then added “No dinner” to the record.
Shopping also gets pushed to the wayside when traveling with children. I had highly anticipated checking out several shops in the city that my native suburbia just doesn’t offer, and I did steal a few moments to browse, though without spending enough time to buy anything. Traveling with such a group as I was, it just ended up feeling hard to justify an experience that no one else would enjoy. In Williamsburg we split up: my husband stayed at the playground (Domino Park—another 10/10) with the girls while I enjoyed a leisurely browse with the sleeping baby strapped to me. I visited a few vintage stores, as well as Ganni (my first time!) and likely would have bought something, except that it wasn’t worth waking the baby to try something on. In the end, the only souvenir I came home with was a copy of Frank O’Hara’s Lunch Poems—New York just seemed like the place to buy it.
If your goal is to visit as many playgrounds as possible in a given city, and to view them with a critical eye, I do recommend traveling with young children.
My highlights: walking the High Line. The Met, though I wish we could have spent more time. Seeing dear old friends who live in the city. Strolling the Upper West Side and soaking in the ambience. Pizza in the Elizabeth Street Garden. The whole day spent in Brooklyn (DUMBO and Williamsburg). Turns out millions of people want to live in these places for a reason!
My children’s highlights: riding the glass-enclosed carousel in Brooklyn. Getting two ice cream cones in one day. Taking the subway. Jumping on a grid of light-up squares at the middle of the One World Observatory.
My baby’s highlights: spending five straight days strapped to someone else’s body. (He really was so, so happy the entire time.)
I’m currently halfway through What Are Children For? by Rachel Wiseman and Anastasia Berg (which I’ve found very sharp and illuminating so far). On this particular journey I often found myself asking What Are Trips With Children For? I told my husband at the tail end of the trip that I needed to formulate a philosophy of travel. Why had we come on this trip with our kids? The answer is that I wanted to go, and I’m breastfeeding; we weren’t going to leave the baby behind, so we might as well bring everyone. And we were treating it like an experiment. For the next ten to twenty years of my life it will be in many ways simpler to travel with our children than to travel without them; we want to see if it’s going to be worth the trouble. I have heretofore considered it a value of mine to travel with my kids—both because I want to travel as much as possible, and because I have some vague dream to make them citizens of the world, conscientious and humble and flexible and adventurous and up-for-anything. I just don’t know whether this trip helped us accomplish any of that. I’m glad we went, but it’s hard to say whether the experience was overall more valuable for the kids than a week at home would have been, or more valuable for us to have as a family than it would have been as a couple. (I also find it interesting that one reason the authors of WACF repeatedly say people give for wanting to remain child-free is so that they can travel. . . Maybe I will further unpack the perceived child-travel binary in a future post?)
Every night of the trip I posted a modest photo dump in my Instagram stories and got more than a few responses from people who told me I was ambitious, adventurous, inspiring, for attempting such a thing. Because I’m part of several Facebook groups for people who make travel with their children a large part of their lives I know I’m not even close to truly adventurous—I recently saw a post from a couple who had hiked Macchu Picchu with 18-month-old twins. But I was flattered and validated by this feedback. I do like to think of my life as a demonstration of how one might be a parent (without child care) and still kind of do what you want. Even if you have to be a little delusional. It’s harder, but think of how good you’ll get to feel about yourself for surviving! When my husband and I returned from a trip to the Netherlands and Belgium last spring, he observed that it was kind of sad nothing had gone wrong—everything was beautiful and wonderful and we didn’t really have any stories to tell. That was not the case this time! (I will spare you the tale of my five-year-old’s legendary meltdown when we landed at the Salt Lake Airport.)
Yes, it was difficult to travel with an infant, a two-year-old, and a five-year-old. But probably easier than it will be with one- , three-, and six-year-olds, or two-, four-, and seven-year-olds, etc. Maybe by five, seven, and ten it will start getting easier again? I’ll keep you posted. (Also, pretty much everything we did was free for kids five and under—a bargain.)
Whenever someone asks my oldest daughter what her favorite part of the trip was, she says, “Everything.” So it’s possible that her remembered happiness will be greater than her experienced happiness. And that’s not nothing!
This is so affirming to read. We tried to go on an (easy, simple) day trip to Montreal this spring with our 10, 6, 4 and 1 year old and it was so much struggle and I left with similar feelings. There is a huge distance between what I'd like to do on a trip to a city (eat interesting food, stroll leisurely for hours, slowly browse shops) and what my children want (Biodome, playgrounds).
The Substack algorithm randomly served me this piece and I'm so glad it did. I love your writing and loved seeing the city through your eyes — and you've made me think so much more about traveling with kids. We live in Brooklyn with our two (5 and 7) and actually haven't done much in the way of trips-to-other-cities yet, but we really want to and think they would get a lot out of it! I'm not sure what's holding us back — maybe lingering lockdown-inspired desire to travel anywhere *but* a city since we felt so trapped here during that time? But you're really making me want to go for it, especially since we are finally past the baby/toddler/preschool ages.
Also (re what if you moved to the city and never went to the Met): We get so cozy in our little easy Brooklyn life and so comfortable knowing the city is right there if we want it, that we definitely don't take as much advantage of it as we should. And we are so happy when we actually do. So: I also love the inspiration here to just get over there a little more frequently!
Thank you for your beautiful, thoughtful writing :-)