Sometimes, a Dream Trip Is One You've Already Taken

We landed on Uruguay precisely because it was new, a chance to collect another passport stamp and revel in our unfamiliarity of South America’s second-smallest country. Every day was a discovery: Atlantic beaches with scorching sand and water that only flirts with being too cold, tannat wine that imparts a buzz not unlike the bite from caffeine-heavy mate, surf hamlets more bohemian than Southern California’s enclaves, and a proudly liberal capital that at times reminded me of my native City by the Bay up north.

Two weeks later, Karin returned to her office in New York City, and I moved into an apartment in Lisbon, committed to a month in another new country. It was there, in a laptop-friendly cafe in Alfama, that I learned the term digital nomad, and there, in my third-floor walk-up in Príncipe Real, that I decided to become one.

This time, however, the question of where to go next did not begin with an appraisal of places I had yet to see. It was answered by the city I’d soon be leaving.

A few months later, after a brief return to the Bay Area, I went back to Lisbon. It felt familiar, like the seat of a chair that was still warm after being curled up in with a good book. Yet despite having a tenuous grip on the language, knowing how to navigate, and having a handful of friends that made it feel homier, the city itself had transformed in my absence: The gray skies I’d been met with in March radiated blue through a July heatwave. The cobblestone streets swelled with tourists, now slick with sweat, not rain. Day trips to nearby Sintra and Cascais became weekends in Geres and Evora. Even retracing my steps in Porto somehow felt novel.

It’s easy to say we’ve been somewhere after a single visit, whether crossing off a country after a two-week tour of the major cities or checking off a capital after hitting the major landmarks. But as anyone who’s taken a staycation or felt the culture shock of coming home knows, even our own cities have the potential to feel foreign: No number of days, weeks, or even months will reveal a place in its entirety, leaving ample room for a second, third, or even 30th visit.

The months that followed my second departure from Lisbon in the fall of 2018 were split between places I’d seen before and those I was seeing for the first time, solo travel and trips with family and friends. I spent a month in an apartment in Shoreditch, London, a now-trendy neighborhood no guidebook recommended the last time I’d been there. A couple of months later, I celebrated Christmas in Vienna and New Year’s in Budapest with my family.

It’d been nearly a decade since I’d traipsed through Vienna on a post-grad Eurotrip with Karin, our first international trip. Yet when my sister, who’d long dreamed of wandering the streets Mozart and Freud once had, proposed Austria, I was quick to suggest we tack on a trip to Hungary. We were too close to pass up a place none of us had been, I’d argued. It was an easy sell: My brother had spent considerable time in Vienna a few years prior while studying abroad in Germany, and my mom had visited the city many times throughout her own college years.

Yet, that first evening, each of us was equally struck by the snow-dusted Rathaus, whether seeing it for the first time or in a new light, in this case the glow of Vienna’s famed Christmas markets. A decade and two seasons later, gluhwein in gloved hand and family in tow, it was an entirely new city to the one I’d equated with young travelers sharing white wine by the Danube.

The truth is that travel is always new. A trip is a moment in time that’s decided by more than just a destination: It’s shaped by the company we keep, when we’re able to get away, and where we are in our own lives. No matter where we go, every trip is its own experience, and revisiting the places we loved is a chance to get to know them better, or in some ways, even at all.

The following summer, Karin and I planned a 10-year reunion tour through Europe. We stuck to the eastern half of the continent to round out our itinerary from the decade prior, leapfrogging the countries she’d been to or had plans to visit. Only this time, when she suggested Budapest, I felt no need to counter with Bratislava just because it was new and in the neighborhood.

It’s tempting to daydream about unexplored destinations when craving a vacation, or pass up places we enjoyed out of a stubborn desire to whittle down the world like it’s a grocery list. For travelers, it’s one of the easiest traps to fall into: Download any dating app, and you’ll see country counts displayed like travel badges in every other bio. Strike up a conversation at any hostel, and the topic will likely turn to travel, with equal emphasis on numbers and experiences.

But now, more than ever, it’s important to show the places we love a little love. Our tourism dollars will matter more than ever in the post-coronavirus era, and it’s up to us to put them to good use. Opt to make new memories in a destination you remember fondly. If you’re able, book a stay at a hotel that anchored your experience the first time around, and patronize the restaurants that turned you on to a new cuisine. Track down locals you met, and see what you can do to support them as they supported you as a newcomer to their city.

Travel will not look the same when the new normal sets in. Neither will our perspectives be unchanged. If ever there was a time to revisit the places we call favorites, it’s now, because just like any individual destination or the very concept of travel, our ever-evolving definition of normal is perpetually new. And that changes the way we experience the world.