People often ask me if I ever get tired of traveling. It’s a reasonable question. I write guidebooks, host trips, spend a disproportionate amount of time thinking about far-flung restaurants, and seem to have made a career out of getting on trains. But no, I don’t get tired of it. That’s partly because traveling for work and traveling for myself feel like two entirely different things now.
Guidebook research requires constant scrutiny. A recommendation can’t rest on a good meal I had five years ago or a hotel I remember fondly. Places change, restaurants lose their way, hotels grow tired, and a perfectly good walking route can be disrupted by a bridge closure or by changes in a neighborhood an occasional visitor would never recognize. My job is to notice everything, verify it, and distill it through the eyes of someone arriving for the first time. I enjoy that work, but it demands a particular kind of vigilance and attention. When I travel for myself, I let all of that go.
That distinction took years to evolve, and the way I travel has changed a few times over. As a teenager, I would lie to my mom, tell her I was going to the library, then hop on a train to Penn Station instead. It had nothing to do with the destination. I was a studious kid stuck in a structured suburban life, and getting on that train was the closest thing I had to an exit. Despite one of the most orderly street grids in the world, I found ways to get lost with astonishing consistency. Sometimes this scared me. I loved it. Getting lost meant I’d successfully left something behind, and that was the whole point.
My first car only expanded my range. It was a 1985 Oldsmobile Cutlass I considered, incorrectly, to be extremely uncool. I’d head toward Philly or New Hope with little more than enough money for gas and food. I don’t remember the museums I visited or the meals I ate. What stayed with me was the pleasure of following my curiosity without having to justify it to anyone. That instinct hasn’t changed, although my destinations, and my reasons for chasing it, have.
By my twenties I was traveling around Europe, and a new instinct took over: completism. I treated every destination as a place I needed to finish. I’d land in a city with a guidebook and not leave until I’d checked off every museum, church, and archaeological site listed inside it. I don’t regret traveling that way. It gave me a foundation I still rely on. But it was a different kind of travel than the aimless disappearing act of my teenage years, closer to an assignment than an escape.
Eventually it became an assignment, literally. When writing guidebooks and leading tours turned into my job, that checklist approach stopped being something I wanted for myself. I already spend my working life being thorough, tracking down every listing, and making sure nothing gets left off. Off the clock, I didn’t want to run the same drill. I wanted to feel lost again, the way I had as a teenager. I wanted a sense of place instead of a list of sites, and I wanted to spend my time with people instead of monuments.
Lately I’ve been stealing whatever time I can find between deadlines. Work has been relentless, between writing a Venice guidebook, building Deep Dives, and trying to bring Parla Cucina cooking school to life. There are weeks when I look up from my computer and realize I’ve barely left my neighborhood. That’s usually my cue to pack a bag.
Last week, I spent a couple of nights on Giudecca. I had been to the Venetian island plenty of times, usually to get my boat cleaned or to install a new engine. In and out. This time, I wandered away from the waterfront and found myself looking at apartment buildings beside the shipyard. Before long I was reading about the redevelopment of the Junghans factory and the work of Gino Valle, wondering how I’d managed to overlook an entire chapter of Venetian history. I know far more about the Republic than I do about postwar housing. I have degrees that make me reasonably competent when the conversation turns to antiquity and the Middle Ages, but twentieth-century architecture is another matter entirely. I liked that feeling of being ignorant, because it reminds me how easy it is to mistake familiarity for knowledge.
A few days later, I ended up in Tor Tre Teste in Rome for much the same reason. Richard Meier’s church may be the neighborhood’s best-known landmark, but it wasn’t what held my attention. I kept looking past it, at the ordinary streets and housing blocks, at how the neighborhood fit into a Rome that most visitors never see because they’ve been taught to stop looking once the ancient monuments and Baroque churches run out.
I don’t think these trips make me a better traveler. They make me a better observer, and that’s an important distinction. Travel has become strangely performative, often driven by FOMO and TikTok trends. Left on my own, I move much more slowly. I’ll spend half an hour trying to understand why one block feels different from the next, or why a building seems oddly out of place. Sometimes I find an answer. More often I go home with another book to read.
Months later I’ll recognize one of those afternoons in something I’ve written. A neighborhood I wandered through without much purpose ends up folded into a tour, or a conversation sends me back to an archive I’d otherwise never have revisited. For someone whose work depends on planning, those unplanned days have become indispensable. They remind me that curiosity has always been a better compass than an itinerary.
