How I Learned to Take My Family Along for the Ride
I got my wife and daughter to love cycling—with a little help from Italy
Outside's long reads email newsletter features our strongest writing, most ambitious reporting, and award-winning storytelling about the outdoors. Sign up today.
For the last ten years, I’ve been carrying on an affair. It’s gone on in full view of my wife and daughter, it’s been broadcast widely on social media, it’s been chronicled in major publications. While I can’t say it’s been entirely positive for my marriage, or my family, it’s given me deep and lasting fulfillment. It’s made me feel young and will probably help me live longer.
The object of my torrid affection has been the bike. Ever since taking up road cycling, it’s been an undeniable thing in my household. The hidden receipts of new bike purchases, the taking up of otherwise livable New York apartment space by an ever growing fleet. And of course, the weekend training rides that inevitably go on too long—I’ve set Strava KOMs trying to make it back for a kid’s birthday party (where I was the guy huffing down pizza slices in the corner).
It’s not that my wife, Jancee, and my ten-year-old daughter, Sylvie, don’t ride bikes. With manic determination, I had Sylvie fully pedaling at age three; at six she landed on the podium in a kids’ mountain-bike race that I had entered her in on a whim. We’ve ridden en famille a few times on various rail trails in the U.S. But my cycling life has been largely compartmentalized; those 45,000-plus road miles I’ve racked up—more than many people ride in their entire life—have been done largely without them.
There are plenty of reasons to ride together. To name just one, research suggests that couples who went through challenging experiences together reported greater relationship satisfaction. Summarizing the research, The New York Times explained: “Scientists speculate that your level of commitment may depend on how much a partner enhances your life and broadens your horizons.” In other words, the family that bikes together, stays together.
But my cycling life has been largely compartmentalized; those 45,000-plus road miles I’ve racked up—more than many people ride in their entire life—have been done largely without them.
So when the offer came from DuVine, a Boston-based “cycling adventure” company, to do a family bike tour in Puglia, Italy, I jumped. Unlike many cycling trips, which are oriented around adults of similar fitness levels, this one was intended to bring adults and kids together on the road.
Here was the chance, I thought, to try and pull the family more fully into my cycling fold. I could use the temptations of an Italian holiday as a gateway drug to what I hoped would become a full-blown cycling addiction—replete with more bike outings—on their part.
The trip was, after all, pretty cush: fantastic hotels, the bounty of one of Italy’s best food regions, and an entirely forgiving amount (to my mind, anyway) of actual bike miles traveled. Whatever the mileage, it was real cycling, not just a short jaunt on a multi-use path but hard climbs, twisty descents, and cobbled villages out on Italian roads. And it wasn’t just cycling—there was mozzarella making, snorkeling, horseback riding.
Best of all, I wouldn’t be in charge of procuring the bikes, picking the route, or really any logistics at all. I, like my wife and daughter, just had to show up and ride. “Bike/Eat/Drink/Sleep” read the T-shirts DuVine sent us ahead of the trip. I dare you to show me a problem with any of this.
Still, I hesitated. Jancee likes riding a beach cruiser to Dairy Queen wearing a dress. How would she like grinding out climbs in the full sun of a Mediterranean summer, out on the open road? It can be an uncomfortable experience for any newbie.
Sylvie, while proficient on trails and paths, had limited on-road experience, mostly because we live in a place where a recent spate of cyclist fatalities has been declared an “emergency.” The number of children who regularly ride bikes has been declining in the U.S.—the blame is attributed to everything from video games to traffic danger. And while girls and boys seem to ride at equal rates, there’s a “significant drop-off” for girls at age ten, and it only grows bigger. Even in progressive cities, like Seattle, male cyclists vastly outnumber female ones. What was meant to be a holiday was starting to seem like a political act. We opted in.
As the trip drew near, we furiously prepared. With six weeks to go, Jancee began spinning at her gym in an effort to build up bike fitness. Sylvie set out to master her newly acquired GoPro so she could document the trip. I went into planning and packing mode, raiding my cycling closet to make sure everyone had the right riding gear. This was all reflexive to me, but I suddenly realized that we were in heretofore unexplored territory when, after first explaining to Jancee that one didn’t wear underwear with cycling shorts, I suggested she could use my chamois cream, the one I had blithely applied near my nethers countless times. She opened the container, and, noting the tangy, rosemary-inflected scent, shot back: “In what universe do I want this getting into my private parts?”
A few weeks later, we were gathered in the street outside our hotel, the Palazzo Ducale Venturi, a handsome 16th-century mansion that once belonged to a duke, in the small town of Minervino di Lecce. Our DuVine guides, Paolo and Davide, had put out a little table filled with pre-ride necessities, including wipes and almonds. In a nice, particularly Italian touch, there were sprigs of fresh mint and lemon to add to our water bottles. As Jancee adjusted her bike’s saddle with Davide’s help, I suddenly noticed she had a chain-grease mark on her calf—that ultimate novice’s rite of passage. I flushed with pride, like she’d been anointed to the Sacred Order of the Velominati.
We proceeded into the narrow streets of Minervino, led by Davide. As I heard a car approaching from the rear, I advised Sylvie to move right a bit. When I heard another one, I warned her again. After the fourth time or so this happened, she snapped back, “I know. You don’t have to tell me every time.” After that, I told her I was warning her mother—who actually liked getting the status updates.
I was conflicted. On the one hand, we were encountering situations that were, for my daughter, novel: an Italian roundabout, which can baffle even an experienced adult, or a twisty oceanside descent. On the other, I wanted her to be gaining her own sense of confidence and skill.
Midway through the first day’s riding, I changed my strategy. I stopped issuing directives but rode just off her wheel, slightly to the left, on the theory that a driver who might not see her—low as she was to the ground—would surely spot me. I was also performing the dark calculus that it was better for me to get hit than her. I was, theoretically, lowering her risk without lowering her sense of ability.
Before we set out, I’d been worried about Italian drivers, who surveys have rated Europe’s “scariest.” But while Italian traffic can seem menacing—the sound of those high-revving diesel engines reverberating in narrow streets—drivers in Italy are generally quite accommodating to cyclists. The rare honk is usually meant to alert, not intimidate. And the cars are smaller: none of those cartoonishly outsize pickup trucks with huge protruding mirrors that clog America’s roads.
We rolled down country roads lined by stone walls, through endless olive groves—Puglia is Italy’s main olive-oil-producing region. Under an act of Mussolini (“One of the few good things he ever did,” Davide said), the big olive farms had been broken up years ago, so that today, almost every family seemed to have a small olive orchard.
We paraded through small towns where nonnas kibitzed on street corners and old men played dominoes at cafés—they often stopped to smile at the sight of a pink-jerseyed kid. We marveled at the trulli, the iconic, conical, white-painted shepherd’s houses. We visited one of a series of ancient towers, where fires would be lit à la Lord of the Rings to warn against Ottoman invasion, and were rewarded afterward with a cracking descent to our lunch stop. And, oh, lunch: fresh-caught, glistening sea urchins; plates of warm, quivery burrata; pureed fava beans and chicory. Jancee was suddenly warming to long-distance cycling’s tendency to vaporize calories.
My plan seemed to be working. Paolo and Davide, meanwhile, kept up my wife and daughter’s spirits whenever their energy flagged on the road. They would spray Sylvie with water bottles or point out roadside Mediterranean herbs to Jancee. Davide, a former chef who had lived in Scotland for many years, was solicitous and sincere; Paolo was an irrepressible free spirit who had traveled the world rescuing dolphins and learning Reiki. When not chiding Davide, he’d issue passionate pronouncements: “We Italians work to live. We do not live to work.”
After we hit 12 miles on day two, cracks were beginning to show. The temperature was above 90 degrees, and we were on a series of undulating climbs. Here’s where I had an epiphany, rather obvious in retrospect: Kids don’t like suffering for its own sake. Kids like to have fun. They may like biking for the sense of freedom and mobility it gives them, but they don’t want to hear your tired slogans about pain being weakness leaving the body. And so, as we neared the town of Otranto, Sylvie jumped into the sag wagon, and Paolo whisked her away to a gelateria.
When I later asked DuVine’s president and founder, Andy Levine, about how kids tend to fare, he hinted that family trips often have adolescents who can ride their own bikes, or kids being pulled in trail-a-bikes, but few that fit in between, like my daughter. “You are correct that young children often do not want to be on the bike very long,” he said—which is why the trips are usually loaded with other activities.
And indeed, the next day, we were kayaking to a secluded rocky coast, where we plunged into the warm, clear waters of the Adriatic. Paolo, himself a freediver—he gained Sylvie’s undying admiration when he rescued her dropped GoPro from 30 feet below the surface—noted how much she took to water. A few days later, we snorkeled the submerged ruins of a Roman pier, spotting shards of the broken amphorae that once held wine and oil from distant traders. Sylvie thrummed with a new energy. I needed to recalibrate my expectations about my daughter and focus less on what she was capable of than what she wanted.
And in many other ways, the trip was a huge success. Jancee, despite having done essentially zero road cycling, soon became accustomed to the initially anxiety-producing presence of cars and tackled the hills with reserves of grit.
I needed to recalibrate my expectations about my daughter and focus less on what she was capable of than what she wanted.
More broadly, I got to put my skill set to broader use. I wasn’t just dadsplaining—i.e., supplying half-baked, semi-informed answers to questions like “Do fish have ears?”—as I doled out riding tips. For once I actually fully knew what I was talking about! And I had an unexpected victory. At home, Jancee and Sylvie would often roll their eyes as I returned from a hard ride and sank into the couch, nursing a cold drink—or ten. After a few days, they were starting to feel the effort, and I noticed a dawning empathy.
And more importantly, I think they were finally getting a sense of why I was so drawn to riding. There is no way to see more of a place, immersively, than cycling; those drivers who passed us weren’t getting the scents or sounds that we were. With a gorgeous sea as a backdrop, Paolo would occasionally stop to pluck bits of wild fennel, asparagus, and blackberries for Jancee to sample. She was starting to get it. Before, I would have tried in vain to relay these sorts of experiences to an impatient audience—and I’ve learned that a partner who’s been child minding while you were off on a fabulous cycling trip isn’t that interested in hearing of its awesomeness. Now we were creating stories and memories we could share among ourselves, and learning that the best family road trips happen on two wheels.