Traveling With Kids

The Colonnade Hotel, Boston, 7AM

Well, there you go: our first vacation as a family of four is under our belts. (Photos from the Boston leg are coming up on The Cut in a few days.)

Not gonna lie: I thought that taking a six-hour (each way) road trip and sharing a room with a newborn and a toddler (in Boston; we had separate rooms in Maine) would be sort of seventh-circle-of-hell-ish…but it turned out to be not just okay, but great.



The major reason I think it was so much fun was that we were super-prepared…and then flexible when we had to be. So: here’s what worked for us…and what didn’t.

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– Provide morning sustenance. Getting out of a hotel room with two children is difficult; getting out of a hotel room with two hungry children is a nightmare. Keep some simple breakfast food (single-serving yogurts, orange juice, et cetera) in the mini fridge to buy yourself some time to get ready for the day.

– Know where you’re headed. You know how you used to go on meandering walks through new towns in search of a cute little cafe to stop at? When you have kids, you’re doing all that meandering with a thirty-pound person on your shoulders. Playing it by ear is fun, but it’s best to always know a spot or two in the area you’re visiting that you can hit up in a hurry if a food (or bathroom) break is needed ASAP.

– Keep the itinerary loose. The reality is that children have a limited lifespan when it comes to outings, so it’s best to have a general idea of what your plans for the day are…but even more important to bend your schedule when you need to. Sure, you may not want to skip seeing a particular site or eating at a special restaurant, but if your kids are exhausted or otherwise seriously not in the mood, it’s probably not going to be fun for anyone. Focus on the experience that you’re having together, not the experience you “expected” to have.

– Relax the rules. Our son isn’t allowed to watch TV during the day. Guess what? On vacation, that iPad buys mom and dad an extra hour of sleep, so AM cartoons it is. It’s vacation; it’s a good time to chill out and let everyone be a little bad.

– Make time for naptime. When you’re having fun discovering a new town you may not want to put the whole deal on hold so you can run back and sit in a hotel room for two hours…but in my experience, taking that break to let your children have their regular nap at (more or less) their regular time makes everyone worlds happier. Look for ways to make it fun for you and your partner, too: one of you can take your own nap in the hotel room while the other goes to the gym, or shopping, or to the lobby bar (just saying), and then switch off the next day so you each get some alone time.

– Roll with the punches. There will be things that do not go as planned – dinners that are cried through, outings that have to be cancelled because someone throws up, whatever. So this is the most important thing to remember: what matters is not that everything goes “perfectly,” but that you’re together. Because those little disasters, those afternoons when it rains and you end up stuck in the hotel room together watching bad TV or those mornings when you stop to eat at a terrible diner because the restaurant you really want to go to is closed…they don’t ruin your vacation. They’re just one little piece of something much larger, and they only ruin a trip if you’re focused on how things “should be” rather than enjoying what is. The point isn’t to orchestrate a trip that looks great on paper, but rather to launch an experience that’s uniquely your family’s…and then to let what happens happen.

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