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How to Take a Work Trip across Three Countries with Your Three Kids–and No Partner–without Losing Your Mind

I’d been planning a Cuba trip for a while–I had work to do there and in-laws to visit, and I hadn’t been since early 2013–but for one reason or another, dates just weren’t lining up. Finally, the calendar cleared and I secured multiple assignments that would help pay for the trip, so it was game on– time to book flights.

Except I wasn’t traveling alone.

Four passengers = four passports and four visas. (Photo: @collazoprojects)

Four passengers = four passports and four visas. (Photo: @collazoprojects)

My oldest daughter, who would turn six during our trip, had been to Cuba twice, but the youngest, ages 2 and 1, hadn’t yet met their abuela and tias and tio. With a mother-in-law who’s in her 90s, it’s not as if I have the luxury of putting off a visit with the grands. Yes, I needed to work–covering everything from the papal visit to restoration projects and new entrepreneurial ventures–but I also needed to make sure my kids and their father’s side of the family were getting some quality time together.

Only my husband wasn’t going to be a part of the equation.

A complicated immigration status would keep him at home in New York while I sat on airplanes and hauled two suitcases and as many strollers through three airports in three different countries with three children, starting out at 4 AM in New York City and ending up 15 hours later in Havana.

“Are all these kids yours? Are you a sadist or something?” That’s what the US Immigration officer asked when I came back to the US 10 days after I’d left. I just gave him the evil eye. My kids are great travelers.

My two-year old looks out the window on our approach to Mexico City, our layover on the way to and from Havana. (Photo: @collazoprojects)

My two-year old looks out the window on our approach to Mexico City, our layover on the way to and from Havana. (Photo: @collazoprojects)

That being said, enough people asked how I managed to make the trip alone that I thought it might be worth sharing my clutch tips about how to travel alone with three kids on a work trip without losing your marbles.

1. Pack light.
Yes, you’re traveling with kids, but trust me: kids don’t need nearly as much stuff as you think they do. I managed a single carry-on for all the in-transit essentials: diapers and wipes for the youngest, a change of clothes for each, passports and all other IDs, plane tickets and documentation, my laptop and wallet, a camera, a book, my phone, and a coloring book and pack of markers. Kids–even kids who travel a lot, like mine–can be entertained for a good long while with seat back safety cards, barf bags (make puppets!), headphones, and tray tables (sorry, passenger in front of us; I’ll try to keep it gentle).

Don’t pack the entire toy box. And as for all those things you think are essential: My rule of thumb when traveling is to not pack items you can buy at your destination. A caveat for Cuba is that you probably should pack all the diapers you’ll need; diapers can be tough to find and are expensive and of poor quality. Ditto wet wipes.

2. Stay organized.
Keep all the paperwork you’ll need in airports close at hand, organized and accessible. Bring along a notarized letter from your children’s other parent–even though many airlines don’t require them–in which that parent gives her or his consent to take your children abroad. You probably won’t need the letter, but you don’t want to be in a situation where you need it and don’t have it. Because my children carry both my husband’s last name and my last name (and because this confounds so many officials), I also carry birth certificates, a copy of our marriage certificate, and vaccination records as evidence of our respective identities and relationships.

3. Accept help if offered and ask for it if it’s not.
The toughest thing about a 14-hour day of travel was–I kid you not–finding a way to go pee without worrying that my one year old would tumble head-first out of her plane seat and onto the floor. Pressing my five year old into service worked for much of the trip and those tasks where I needed an extra set of hands, but never when I needed to go to the bathroom. I searched for a trustworthy-looking adult and asked them if they could watch my kids for a few minutes.

4. Trust your oldest with age-appropriate responsibilities…
… and reward them with praise (and, if you can, a special treat) for shouldering an extra load. My five year old pushed one of her siblings in a stroller through all three airports and even operated a special elevator by herself when we couldn’t all fit into the elevator for a single trip. I knew that she was a little scared, but I also told her I was totally confident in her abilities and that I was watching her the whole time (which was true). When we had a free moment, I bought her a small bag of chocolate-covered coconut as a thank you.

5. Know your danger zones.
I wish I’d thought to ask whether my airline, Interjet, had milk on its afternoon and evening flights, as both of my youngest children drink milk from bottles. It does not– it only has milk available on morning flights. On the last leg of our return flight home, I had no milk and kid #2 spent the last 20 minutes curled up in the fetal position on top of his tray table.

6. Ease your reentry.
I scheduled in a two-night layover in Mexico City on our return trip, mainly because I love Mexico City, my former home, and because I had some reporting work I needed to do there. But it also ended up being a welcome way to transition between Cuba and home, what with a comfy hotel bed, running water (which we did not have in Cuba), and a room service splurge. If you can break up your travels into more manageable bits, it will be easier on kids… and on you.

7. Take advantage of Trusted Traveler, Global Entry, and similar services.
When booking your tickets, make sure you elect for TSA pre-check if you’re eligible, and take advantage of your trusted traveler/Global Entry memberships if you have them so you don’t have to wait in line for ages when you return home.

8. Bring snacks. Lots of snacks.
Cheerios, fruit chews, apple bars… these are my go-to snacks for kids when we’re on the road or in the air. A snack produced with a parental flourish at the precise moment preceding a meltdown can prevent crisis.

Also, if traveling in areas where you’re not the one in control of when, what, or how you’re eating (as was the case at my in-laws’), bring some breakfast basics for your kids. Instant oatmeal is the best choice; it packs flat, weighs practically nothing, is easy to make, and is filling.

9. Have a clear work plan.
I had A LOT to do in Havana, and while I had my sister-in-law and niece to help care for the kids, I was still the one who had to fit all the usual parenting tasks in at the beginning and end of the day. Being organized before I landed and staying organized each day by following a work plan I’d set for myself was essential to not losing my mind.