As a travel writer, who has often ventured across the globe alone, there’s one thing I know for sure: experiences are more meaningful and treasured when shared with others. You can bring home photographs and stories and tell your family what it was like to visit Dubai’s Burj Khalifa, the tallest building in the world. You can try to explain what it felt like to wander through Bali’s Goa Gajah, the elephant cave, in the dark. You can describe the panic you felt when you lost your way on a hiking trail in Switzerland and didn’t have a map. In the end, your memories are yours and yours alone.
Solo travel is valuable and worthwhile, but traveling with my family is my favorite thing to do, and we've had countless adventures. My three boys each grappled with a nearly 400-pound sumo wrestler in Japan; the five of us hiked to Inti Punku, the Sun Gate, and marveled at Machu Picchu in Peru; and we all went white water rafting in Colorado. Traveling with my kids is the thing I’m the proudest of as a parent. My boys have become thoughtful humans with a global perspective as they’ve met people from around the world with different beliefs, economic backgrounds, and physical abilities.
My littles have been uncomfortable, exhausted, and scared while traveling. They’ve hidden in a door jamb during an earthquake in Osaka, seen their father give chest compressions and mouth-to-mouth to an elderly woman who had collapsed in a taxi line, been separated on a hiking trail, and walked upwards of 20 miles in a single day. Things have gone wrong on trips, flights have been canceled, plans have been derailed. There are opportunities to learn through the struggles and disappointments, to have deeper conversations about what is happening in the world all around, to realize how our actions affect others, and to see how we operate as a family, getting from point A to point B.
My three boys are like a tumbleweed of puppies, constantly romping around in a playful pile, and when you pull one puppy out of the orbit of the pack something magical happens. You realize that your kid, traveling with you one-on-one, has completely different opinions, musings, and behavior than when he is a part of his normal feral little cluster. When there’s only one other person to consider, travel decisions are made together in great consideration of independent interests.
I’ve had the incredible opportunity to learn about each of my children as individuals while exploring destinations across the nation and in different countries. And, of course, as they age and get bigger, flowing through milestones while gaining a more complex understanding of the world, they change. Your adventuresome, chatty, and goofy six year-old might morph into an introspective and cautious preteen. Travel is a chance to dial into your kid, meet them where they are, and strengthen your relationship.
When I travel with one son, I pay him to be a journalist-in-training. He’ll earn one dollar per well-thought out question that he asks to the taxi driver, the maid, the server, the museum docent, the shopkeeper, the kids playing by the fountain. If he wants to earn some pocket money to spend on our trip, he’ll have to make eye contact and muster up the courage to interact with strangers and learn about their city, profession, or perspective. Often these questions are interjected when I’m already chatting with others, but as long as the connection is made, it counts.
Traveling With My Middle Child
My middle son, Sage, is the most intrepid traveler and you can usually get him to do—or eat—anything. Once, when we were in Hakone, Japan, waiting for our train to leave, Sage (age 10) noticed that a car full of elderly Japanese women were watching him from the train waiting to depart in the opposite direction. Rather than look down at his feet or become embarrassed, he waved and blew kisses. The women laughed, covered their smiling mouths, tossed their heads back, and waved right back.
The first trip I took with just Sage was to San Francisco when he was seven years old. He giggled with a toothless smile as we flew over the Golden Gate Bridge on the top story of a red double decker tour bus. We took photos behind bars at Alcatraz Island; shopped at Lefties, a store full of goodies made for left-handed people at Pier 39; posed in front of a cable car at Powell and Market; saw a man swim in a speedo near Ghirardelli Square; walked down Lombard Street, one of the most crooked streets in the world; visited Madame Tussauds wax museum; marveled at graffiti art at the corner of Haight and Ashbury; flipped pages of books at the famous City Lights Booksellers & Publishers; put coins in dozens of coin-operated vintage arcade games at The Musée Mécanique; and hugged gargantuan trees in Muir Woods.
After saying goodbye to the workers at the tiny Golden Gate Fortune Cookie Factory, located down a narrow alley in Chinatown, an elderly woman with a curved spine and bundles under her arms approached us and asked when our birthdays were. She told us that Sage’s Zodiac animal is the rat and mine is the horse and because of this we would never get along. We learned that day that we must be in charge of our own fate, never take for granted our bond, and to be kind and respectful to others, even if we don’t subscribe to their philosophies.
My Trip With My Youngest Son
The first trip I took with my youngest son, Kai (not counting a visit to Montana to see his grandmother when he was a baby) was to Scottsdale, Arizona, when he was just five years old. Kai spent hours swimming in the pool at The Phoenician with a new friend and when we were set to leave, I heard him exclaim, “Wait, you’re a girl?!” We noshed on finger sandwiches and little desserts during the Afternoon Tea, tried our skills at trapeze, and enjoyed playing in the surrounding desert full of cacti. Kai made candy bracelets and fed the ducks at the Kid’s Club while I indulged in a spa treatment.
The highlight of the weekend for me was adventuring on Cholla Trail on Camelback Mountain. Kai didn’t want to do the hike and he made me carry him the length of the road that we had to walk from the hotel to the trail head, which was about a half-mile. I was nervous that he wasn’t ready for such a hike and that it would end in tears, but once my little guy saw the boulders dotting the desert landscape, I couldn’t slow him down. He posed with a rock that he thought looked like a dinosaur head, pointed out little yellow flowers lining the rim of the trail, and flexed his muscles when we reached the top.
Sharing Adventures With My Oldest
My oldest son, Bridger, traveled to La Jolla and San Diego with me when he was nine years old. That was the first time he had been without his brothers and he missed them terribly. He talked about them constantly on the trip, wondering if they’d like seeing all of the birds flying overhead while we were kayaking or if they’d love seeing the seals on the beach at La Jolla Cove.
We explored San Diego’s Old Town and sampled Mexican food along the way while listening to live mariachi music. We visited The Cave Store in La Jolla, which at first look appears to be a run-of-the-mill tchotchke shop full of souvenirs, but at a deeper gander, reveals a door that leads to a tunnel dug out in 1902. The passageway, created to smuggle alcohol and opium during prohibition, travels down sandstone cliffs 144 steps to a sea cave that has an outline shaped like a man (Sunny Jim). Our last dinner was at The Marine Room, a restaurant built in 1941 that juts out over the sand and has large windows that endure the brunt of the waves during high tide. Bridger ordered a chocolate pyramid and thanked the server.
When we landed at O’Hare International Airport at home in Chicago, and Bridger spotted his brothers, he ran to them and hugged them so hard they all fell to the ground in a heap. A few days away had made him appreciate his siblings in a way he hadn’t before. They talked over each other, animatedly and hurriedly, the entire way home. The puppies were reunited.
My boys are super competitive, always challenging each other on who’s faster, stronger, and better. While we will always take family trips together, and endure quite a bit of quarreling and chaos, there’s something incredibly special about traveling with just one kid in tow. Having mama-son trips are something my kids will remember long into their adulthood. Not only am I able to bond with each son individually, but also, the two kids that are left behind are able to connect with each other and build a stronger relationship. My husband will take the opportunity to build skate board ramps in the garage or jam on guitars or play video games with the boys that are at home. Sometimes you have to see your family from a different perspective and after a great distance apart to appreciate where you’ve been and the relationships you've developed.