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Why Traveling With My Preschooler is Easier Than Traveling Without Him

I’ve long been optimistic about my travel capacity, and frequently operate under the “get there and figure it out!” mantra. Often, it serves me well. But sometimes, travel optimism —and under-packing — bites me in the ass (a particular trip to Denmark and Sweden comes to mind, during which I both got horribly sick and had only packed one pair of pants for 12 days). And of course, having a kid did put a small dent in my freewheeling travel ways — but not at all in the way I expected. In fact, I find it much easer to haul my preschooler with me, be it to Arkansas or to Africa, than to leave him behind.

When my son, Silas, was born in 2015, I planned a solo trip from NYC to California for when he was five months old. No big deal, right? I could leave a 5-month-old with his dad for a few days. But alas: I hadn’t taken into account the huge ordeal that is breastfeeding. And given the choice between a) bringing my baby with me across the country or b) bringing my breast pump and cooler and having to juggle airport pumping, milk packing, ice packs, and TSA regulations for liquids — I gave up and brought the damn baby.

But now that Silas is four, leaving him for a bit should be easy, right? Well, not exactly. His dad and I split when he was 2, and his dad remarried soon after and welcomed a new baby. Silas visits them once a month, but for the most part I am very much living that #singlemomlife. His dad and stepmom live nearby here in Nashville, which is great, but they’re not…so big on communication. For example, I had to hear from my then-3-year-old himself that he and Daddy and stepmom had moved away to a new house — and I had a hard time getting my ex to inform me of our son’s new part-time address (which he was, of course, legally obligated to convey).


This is all to say: While I know my son’s other family loves him and takes care of him, I’m simply not (yet) comfortable leaving town while he’s visiting them. Sure, maybe that’s more about me than about Silas; knowing that, if there were an emergency, I could be there in five minutes flat, lets me sleep at night. I spend Silas’ long weekends with his dad frantically catching up — on work, appointments, friend meetups, dates. But I do not spend them relaxing. For me, I feel the most relaxed when my son is safely by my side.

So here I am, mom to a smart, amazingly self-sufficient, perfectly capable 4-year-old — whom I am, emotionally, entirely incapable of leaving behind when I travel. Which is why, at 4, Silas has now been to seven countries and three continents. Lucky kid! But still: This cannot go on. I knew I had to rip off the Band-Aid somehow. So when the opportunity presented itself for me — just me, child-free — to visit the Florida Gulf Coast community of Alys Beach, which I had long admired from afar, I knew it was time. And I did the previously unthinkable, to me at least: I hired a babysitter.


Don’t get me wrong; my son has had a zillion babysitters ranging in age from 11 to 70 (I am a single mom, what did you expect?!) but never before had I paid someone $300 to sleep at my house in Nashville while I slept in Florida. There was a large part of my brain telling me that this made zero sense, since it would likely take less than $300 to bring Silas to Florida with me. But I knew teaching myself — re-teaching myself — to travel solo was more important than that. After all, I’d done it so much before becoming a mom. I’d bought my first plane ticket (to Mumbai) at age 19 and returned to India three times. I’d backpacked around Europe, lived in Scotland for seven months, and fell in love with underrated Eastern European cities: Belgrade, Budapest, Ljubljana. When I was pregnant, I hiked 11,000 feet in New Mexico. Why on earth was I so afraid of going to Florida without my kid?

I arrived in Alys Beach a bundle of nerves. Lucky for me, Alys Beach is basically a zero-tolerance zone for nerves. This beach community is the picture of minimalist peacefulness, with beautiful all-white buildings basking in the sun like some sort of Gulf Coast Santorini (in fact, Alys’ resemblance to Greece was the main reason I’d been obsessed with it for so long and wanted to visit in the first place). I settled into my gorgeous rental and cracked open a book and a bottle of wine on the terrace. This was the life! I started to believe I might actually be able to hack this relaxing thing. But then I got a text: My boyfriend was running late to pick up my son from school back in Nashville. He had been kept late at work, and I could tell he felt absolutely terrible about it.


I panicked. This was it! Just what I’d been afraid of! I was a terrible mother who had abandoned my son and my fears had been proven true: I, and only I, was capable of actually taking care of him. I had to fly back immediately and continue my life of all-responsibility-all-the-time-and-zero breaks. Let’s go!

But no. Because as hard as it was — is — for my eldest-child, tough-single-mom, Enneagram Type 2 (ugh) self to admit, I don’t have to do it all. Me taking this break, my one true break from my child in four years, was not “abandoning” him. It was not showing him I don’t care about him. In fact, it was showing him I can also care about me. And my son, who is oh-so much like me (an Enneagram 2 in the making, no doubt), is such a helper and a giver and the sweetest of hearts, that I need to set the example for him that it’s okay and good and important to care for yourself, too.

Also, I needed to face the facts: I have built a damn good community for Silas and I in Nashville, and they have got our backs. Within minutes, I reached another mom on the phone who was able to pick up Silas on time, and as they were leaving school they ended up running into my boyfriend who had probably broken every traffic law to get there just three minutes late. They bought Silas and his friends cookies and took them to the playground. And for the next two days, my phone pinged with a regular feed of photos and videos of Silas — from that mom, from my boyfriend, and from the babysitter who took Silas out for pizza, spent the night, and dropped him back off at school. These adults had my back, and Silas’s. I realized I had never gotten text updates, let alone photos and videos, during Silas’ visits with his dad — and I’d never realized how much that not knowing, that not seeing evidence of Silas happy and safe, had weighed on me.


The fear spell (the fear cycle, even) was broken. With every Silas pic I got — he and my boyfriend baking cookies, he and his friends climbing at the playground, he and his babysitter cuddled up reading stories — I felt a weight lift off my shoulders. I walked on the beach. I rented a bicycle. I walked three miles in a nature preserve. I took a yoga class. I chatted with other adults, feeling absurdly unencumbered in this strange, new, child-free world. I poked around design shop MAST Alys Beach without having to remind anyone to just look don’t touch! I was a person, not just a mom, for two days.

When I got home, Silas sprinted out onto the porch in his pajamas and jumped into my arms. But he wasn’t upset that I’d left, or sad like I’d feared — he was thrilled to tell me about all his adventures, about everything he did and saw and learned thanks to the many adults who love and support him. Thanks to our village.

Shortly after my Alys Beach trip, Silas and I headed to Cuba together to research the SheKnows Mom’s Guide to Havana, and I was just as delighted to bring him along as I’ve always been. But I’m no longer afraid to leave him behind, with trusted adults, if that’s what the trip — and/or my soul — calls for. Traveling together brings us closer, but traveling alone reminds me who I am — and that while right now Silas is my everything, I don’t have to be his everyone. At least not all the time.

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