We believe—as we’re sure you do—in starting them young. But often with kids, the best-laid plans are just that, and things can go off the rails when you’ve planned one too many museums or get caught without pens on the plane or snacks in your bag. So we decided to launch a column dedicated to family travel—tapping parents who are always adventuring to share their strategies for everything from packing to mid-air meltdowns, go-to clothing and equipment, and their favorite kid-friendly hotels and destinations. First up? Our own head of strategy, Maeve, who first came into my world 17 years ago as our babysitter when Clara was five, back when I was the travel editor at Cookie magazine and doing my own travel blog, Travels with Clara. She was smart, scrappy, and super creative, and when I was hired at Martha Stewart Living, I brought her there with me. From there she came with me to Traveler, and I’ve been pining for her ever since she left when we did. In a full circle moment, Maeve now has little kids and has just started working with us, and came up with the idea for this column, which we’ll be doing once a month. —Y.E.
Name: Maeve Nicholson
Home base: NYC
What you do: Head of strategy & growth at YOLO and Wm Brown Project
Paint a picture of your family—how many kids do you have and how old?
Two girls: Winnie (5 years) and Rocky Joy (3 years)
At what age did you start taking them on more challenging trips?
My husband and kids’ dad is Australian, so we dove straight into the travelsphere when Winnie was just two months old to spend the holidays Down Under. A lot of my friends were horrified that I would take her on a 26-hour flight, but honestly, a two-month-old mostly eats and sleeps, which is exactly the kind of energy I try to channel on long-haul flights.
What are a couple of the most successful trips you’ve taken as a family?
Success is defined by many metrics, but I would have to say our favorite trip so far was our most recent, to the Aeolian Islands and Sicily this August. My kids are finally old enough to really “get it.” Since they’re not technically babies anymore, it’s been amazing to watch them notice things, ask questions, and actually see the world through a new lens. I didn’t travel much as a kid, so watching their little worlds open up, whether it’s tasting something new or looking out a hotel window that feels straight out of a dream, has added a whole new layer to travel for me.
Do you do anything special to prepare your kids before a trip or certain destination?
For our Sicily trip (partly thanks to YOLO’s postcard from Salina), my husband and I read The Leopard. But I also love hyping my kids up before a trip with bedtime stories loosely connected to our destination—in this case, we read Strega Nona. Once you’re home, the books become sweet little souvenirs for your library.
Any organizing hacks when it comes to packing a suitcase?
I’m obsessed with packing cubes (Thule are my current favorite), and I honestly don’t know how I ever traveled without them, even pre-kids. I like to organize by activity—so swimsuits, casual clothes, and nicer outfits all live in their own cube and are easy to grab. If I have the space, I always toss in an empty one too, which is perfect for corralling the deeply dirty (disgusting?) clothes that inevitably pile up by the end of a trip.
What are a few essentials that you pack for your kids on most trips?
Both my kids have gotten into the somewhat ridiculous habit of wearing opulent, feather-trimmed faux-silk pajamas to bed, but on our trip, they actually came in handy. They doubled as cute plane outfits, and at the end of the day, they were still pajamas, perfect for catching sleep in transit. With a cute hair style and slip on shoes, dare I say they are also dinner appropriate? The button-up tops also made for great layering pieces, which felt unexpectedly practical for something so over the top.
These soft Bluetooth headphones were an amazing find. They double as a sleep mask, and allow your kid to drift off without losing an earbud. (See below re: MELATONIN!) Genius. We also never travel without these over-the-top goggles, a real rebuke of quiet luxury. A lightweight jacket always earns its keep, and I swear by ballet flats since they are foldable, chic, and surprisingly versatile. And finally, I cannot overstate the importance (forgive me for being obvious) of tote bags. Beach toys, shopping, wipes, diapers, snacks, interesting rocks, the list goes on but they can do it all. I’m partial to ones that double as a cute “lunch purse,” but are in reality a modern upgrade to Mary Poppins’ bottomless everything bag.
Do you have any go-to tricks for preventing meltdowns mid-flight?
I love turning a Muji hanging dopp kit into a kids’ travel kit. I first saw the idea floating around Pinterest, but I like to give it a little upgrade: fresh crayons, cool sticker packs, maybe a tiny toy or two tucked into the zip pockets (gum for altitude changes! Hand sanitizer! Bandaids…). The genius is in the design since the hanger means you can hook it onto a tray table latch or seat pocket so everything is visible and within reach. It’s the perfect thing to bust out during those high-risk moments when meltdowns lurk: pre-takeoff boredom, or the during descent when the iPad is on 5% and WiFi has vanished. For older kids, you can slide in slim paperbacks, comic books, or paper dolls so the kit can be a fit for almost any age. Essentially, it’s a portable bag of crafty, fun activities that feels exciting, keeps them occupied, and most importantly saves you from fishing crayons out of the seatback pocket.
How do you get them to sleep on a long-haul flight?
Melatonin, melatonin, and melatonin. At home, we’re pretty “hippy-dippy” for the most part, but when it comes to long flights, all bets are off. We once made the disastrous mistake of booking a 4 p.m. flight from NYC to Rome, and never again. The lights never really dimmed, and just as the kids’ eyelids started to droop, we were touching down. Now I swear by booking the latest red-eye that’s reasonably possible. Melatonin plus screen time via downloaded YouTube videos and they’re out like lights. One tip: do a “melatonin test drive” a few days before you travel. It’s harmlessly soporific in small doses for most kids, but I’ve heard it can also have the reverse effect. High energy levels at 30,000 feet is not the kind of turbulence anyone needs.
Do you have any travel rituals with your kids that have become tradition?
Not exactly groundbreaking, but postcards are one of our sweetest travel rituals. Whether you’re sending them to grandparents or mailing them home as little notes to your kids’ future selves (trip highlights, or even just a doodle), they double as both memory-keeping and a kid-friendly activity. They slip neatly into that dopp kit and make the perfect no-mess craft. The only snag is the stamps, so keep an eye out for a local post office. Luckily, many hotel concierges can also handle this, often making it as easy as dropping your cards at the front desk.
Picture approach: are you iPhone-only, or do you travel with film?
Retired hipster that I am, I still travel everywhere with my Polaroid. The kids get such a kick out of it and my eldest now thinks she’s Slim Aarons. Honestly though, I can’t recommend it. The newer Polaroids are temperamental at best, and the film eats up precious suitcase space. What I do love, though, is the idea of tossing a few disposable cameras into your suitcase. Low stakes, no stress: if they lose it or break it, who cares?
Screens during vacation: survival tool or slippery slope?
Jet lag and late nights are basically part of the package with family travel, so instead of fighting it, we’ve started leaning into screens when we’re fighting the nod. Before a trip, I’ll download a few of my favorite childhood movies (Labyrinth, Chicken Run… I could go on, but I’ll spare myself the embarrassment) and rebrand a nightmare-ish evening of meltdowns into a “family movie night.” The upside? If it’s a film you actually loved as a kid, it’s really fun to curl up and watch it with your own children. And if you’re really feeling wild, crack open the hotel minibar. Why not splurge on some overpriced chocolate covered nuts? You’re on vacation!
Strategies for traveling with picky eaters?
Before becoming parents, our pre-trip ritual was to avoid anything even loosely related to the cuisine of our destination. Kids, however, have flipped that strategy on its head. I’ve had much more luck doing the exact opposite: in the weeks leading up to a trip, start sneaking in as many flavors from your destination as you can, and see what sticks. Your local interpretations of dishes are perfect warm-up meals, and if you live in a city, you can probably find a specialty shop that carries the real-deal baseline snacks from your destination. Get them hooked early and you won’t be scrambling for Pirate’s Booty and fruit pouches. I also love shopping at local grocery stores wherever I travel. Bringing kids along can be a headache, but I think it’s worth it. On our last trip, my 5-year-old discovered an Italian yogurt brand she became completely hooked on, and just like that, a grocery run shifted from a chore into a semi-fun family outing.
What’s your strategy for eating out at “grown-up” or fancy restaurants with kids and what have been your favorites?
This summer, while in Salina, we visited Hotel Signum’s Michelin-starred restaurant and were pleasantly surprised to find that not only was there a fairly extensive kids’ menu offered during the tasting, but the staff couldn’t have been more kind or accommodating. I’ve also found that even the most elevated dining experiences feel infinitely more kid-friendly when they’re alfresco. It’s a strategy we rely on often in New York, especially when attempting anything remotely “fancy” with kids in tow. Dinner at Altro Paradiso, Charlie Bird, La Mercerie, or Balthazar? All totally kid-friendly under one condition: secure an outdoor table. Ideally, one with a heater as the weather turns crisp.
And as I always say: when in doubt, email ahead. Since having kids, I’ve been surprised by how many restaurants are genuinely welcoming to families. Some of our most peaceful meals have been at high end establishments that happily wrote back to say they would be glad to host little guests. Of course, it depends on the place, but sending that quick email is worth doing for peace of mind
Favorite family-friendly hotels or resorts you’ve been to?
I have to say we were totally blown away by Su Gologone in Sardinia. It’s one of those truly special places with amazing food, warm staff, and a property that feels like it was designed for kids to explore—you don’t have any regrets not leaving the property. (There was also a very sweet stray kitten there that led me down a brief Google rabbit hole around rules and regulations for bringing foreign animals back to the U.S.) We also really enjoy The Miami Beach Edition, specifically because of its two pools. The larger shaded pool has naturally become the “kids’ pool,” and the hotel gets it completely right by keeping the energy relaxed and family-friendly without feeling overrun (or, dare I say, gross). And finally, a shoutout to The Rittenhouse Hotel in Philadelphia, which I have a huge soft spot for. It’s not the most modern, but it’s incredibly beautiful and elegant in that old-school way, and perfectly located for exploring one of the most underrated cities to visit with kids. (And of course it has a pool.)
What’s your policy on souvenirs?
I like to buy things that are actually useful on the trip. While I’d normally cringe at dropping ~$30 on a kids’ water bottle in NYC, on vacation it doubles as the perfect souvenir, and one that starts earning its keep the minute you leave the shop. Once home, every refill becomes a little reminder of your trip.
Of course, the inevitable floaties and cheap plastic toys will always be a dangerous temptation (in a small Sicilian seaside town, we couldn’t even escape Laboubous…). But I try to steer us toward flea markets or thrift shops instead. In Palermo, we stumbled across a Sunday flea market and found two small, porcelain ballerinas—one in pink, one in blue, and just €3 each. They instantly became my 5-year-old’s most precious cargo, lovingly wrapped in and unwrapped from bubble wrap at every hotel. There’s something about these small, inexpensive treasures that end up feeling more beloved than a suitcase of plastic junk. And if they do lose a limb or two along the way, being out just a few euros is far preferable to hauling home an entire carry-on of cheap toys.
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