What Twenty Years in This Industry and Becoming a Parent and Nanny Employer Have Taught Me About Traveling With a Nanny

I've been in this industry for over twenty years, first as a nanny myself, then for the last fifteen running this agency, but the perspective that's actually changed how I think about all of this is the newest one: I'm a parent now, I employ a nanny, and I've traveled with them as a family. Being on all three sides of this, nanny, agency owner, and employer, has been eye-opening in ways I didn't expect even after two decades in the industry. Nothing teaches you what actually matters on a trip like living it yourself.

A quick note before the stories: even in a pretty basic, no-frills nanny position here in the Triangle, some amount of travel, usually one to two weeks a year, is a pretty standard expectation. Sometimes that's a family driving to the coast, sometimes it's an international trip, sometimes it's a week visiting grandparents out of state. This isn't some rare, premium add-on. It's baked into most of the positions we place, which is exactly why getting it right matters so much.

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What Traveling Without a Nanny Looks Like

We've also done trips without our nanny, and I'll be honest, it's hard in ways that are easy to underestimate. You lose the childcare you're used to having locked in, so you're more "on" as a parent the entire trip, in a location where nothing is set up the way your house is. You're baby-proofing a rental from scratch. You're hanging blackout curtains because nobody thought to check if the bedroom had them. You're figuring out where the nearest grocery store is in a city where you don't yet know what any of the stores actually carry. We spent a month in Europe after having our son, and that one was a real adjustment. You're also learning the walking paths, which routes are fine and which ones you want to avoid at certain hours, and trying to figure out ahead of time what simply won't be available where you're going, so you can pack for it. That might be the specific diaper brand your baby is used to, a particular baby food, or some kitchen gadget you need to make the one thing that actually gets your kid to eat. It's not that either way is wrong, but switching locations with little kids in tow comes with a level of logistics that's easy to forget about until you're standing in an unfamiliar grocery store trying to read labels in a language you don't speak.

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The Attic in Maine

A family came to us years ago to hire a nanny and decided to go with another agency instead. No hard feelings, that happens. They made a good hire.

Two months later, their nanny called us. She was quitting. Not because of the kids, not because of the job itself. The family had rented a house up north for the summer and put them in an unfinished attic space, no AC, a cot, and a bathroom down a full flight of stairs. When she said something, the response was that they should be grateful to get out of the North Carolina heat.

She left. We placed her with a family that got it right, and she’s been there six years now.

I think about this one a lot because nothing about it was malicious. It was an afterthought. Nobody sat down and thought "where will she sleep," it just wasn't part of the planning until it became a five-alarm problem. 

That's the pattern I see over and over: the trip gets planned in full before anyone thinks about the person who's making the trip possible.

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The One Down the Road That Got It Right

Same state, different summer, totally different outcome. A family with a few young boys rented a smaller, older house, and told us upfront it wasn't fancy, but they'd clearly thought about their nanny before that person ever arrived. They had their own floor, their own bathroom, and a pullout they'd actually made comfortable instead of just accepting whatever the rental came with. The house creaked, so they made a house rule that the kids stayed off the main floor while the nanny was sleeping.

None of that cost extra. It just required somebody to think about them as a person who needed to sleep and recover, rather than a feature of the house.

I had my own version of this, before I was ever an employer myself. I once traveled with a family to a resort where I had my own hotel room, and they had a suite with attached bedrooms for their kids. We were actually on different floors. They took great care of me, I had everything I needed, and because of that, I was comfortable enough to offer something extra: swapping rooms with them for a few nights so they could get uninterrupted sleep while I took baby duty in their suite, and they stayed in mine while housekeeping turned our rooms over. That kind of thing only happens when a nanny is actually well rested and taken care of in the first place. If they're the one fighting for decent sleep every night, they're not going to have anything extra left to offer, and they shouldn't be expected to.

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Say the Schedule Out Loud

Rotational nanny jobs are actually the easy version of this. You're on a plane, you land, you're on duty until you rotate out. Nobody's guessing.

A family trip is messier, and that's why it needs a conversation before you leave. 9a breakfast duty or a 10a sleep-in start, whichever it is, just say it out loud instead of letting them find out at 8:45a the morning of.

Off time is where I see the most well-meaning families slip, and I've had to check myself on this too. Off the clock should mean off the clock. Your nanny is welcome at dinner, at the beach, wherever, but if they're there, it's their choice, not their job, and someone else is in charge of the kids. Here's the actual test I use: if you're running up to grab something for five minutes and ask them to keep an eye on the kids, that's normal, reasonable, the kind of give and take that happens when people like working together. If you want to take an hour-long walk on the beach and hand them the kids for it, that's not a favor, that's an hour of work– pay it. I've seen the line get blurry more than once, usually not out of bad intent, just because everyone's on vacation and it's easy to forget your nanny isn't.

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Resorts Are Designed to Drain Everyone's Wallet, Not Just Yours

If you're staying somewhere like a resort, you already know the game: they want you eating on-site, doing room service, buying from the marked-up little store instead of leaving the property. That's an annoyance for you. For a nanny trying to feed themselves on their own time, it's a real problem if nobody's told them what they're allowed to spend.

The last thing you want is your nanny feeling guilty about ordering food, or quietly choosing the cheaper, less nutritious option because they're not sure what's actually covered. This matters even more in a lot of destinations, where the fresh, organic, genuinely good-for-you choices are also the pricier ones. Make it clear upfront that you support whatever they need to eat well, not just what's cheapest on the menu.

Put a real number on it. Something like, anything under fifty bucks a day, go for it, and if it's regularly running higher, let's talk. That tells them you're actually covering them, resort prices and all, and it also politely rules out seven $30 margaritas charged to the room every night (a gross exaggeration- because who could function with kiddos the next day??).

It also helps to talk through the nights you'll be out. Are they joining you for dinner, or hanging back at the hotel on their own? Either way, say so ahead of time so your nanny can plan their off time. 

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Figure Out the Car Before You Need It

If you're driving, and a lot of our families do the North Carolina coast run with their nanny in tow- work out the car situation before you leave the driveway. Are they bringing their own car? Are they riding with you-  in which case you've just bought yourself two hours of an entertained backseat, but you also need to think about where their stuff goes and whether they can take the car for an errand once you're there?

If they're not driving and won't have access to a car, just build Uber or Lyft into your sense of what the trip actually costs. Otherwise they're stuck at the house with no way to get five minutes to themselves, which can make things a bit awkward.

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The Flight Is Work- And Think About Where You’re Sitting

If your nanny has your kid on their lap for a three hour flight, that's paid time. That part's not complicated.

What's less obvious is that where you seat everyone matters just as much. If your kids are up front with you and your nanny is rows back in economy, they physically cannot do their job. They can't help with a meltdown from four rows away. So flying first class isn't just a comfort call for yourself, it's a decision about whether they can actually do the thing you brought them to do.

There's also just the optics of it, especially with older kids who notice everything. Your nanny in economy while you're up front doesn't go unnoticed- not by them- not by your kids. I talk to families about this a lot and I'm not going to pretend there's a version that removes all the awkwardness. It's your money and your call. Our nannies aren't expecting a first class seat, but it's worth sitting with honestly, for your kids' sake as much as theirs.

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Bottom line

None of this requires a bigger budget. It requires treating the person coming with you like what they actually are on that trip: not just staff- a roommate, someone whose comfort and rest directly determine whether your family actually gets the vacation you were picturing in the first place. I've been on every side of that equation now, nanny, agency owner, and employer, and the families who get it right aren't the ones spending the most. They're the ones who had the conversation before they left instead of after someone gave notice.

All my best and here to share what I’ve learned always, 

Austin