Last week, after ten days in the Bay Area and four in Los Angeles, I left California for South America, kicking off the meatier part of this period of exploration: nearly three months I’ll spend outside the U.S. On the plane it hit me that, though I first thought of going to Chile more than six months ago, I had hardly planned for this experience in the intervening half year. I had eventually decided to go and bought a ticket, and in the previous week I had reserved a bed in a hostel for my first night and talked to several American friends who had lived or traveled in Chile. But what was I going to do there? I couldn’t say—and on the plane I began to realize what that might mean.

It meant that Santiago would be completely open to me and, at the same time, out of reach in the beginning. I hadn’t read about the city, didn’t have a guidebook, and, without internet access in the air, couldn’t begin to look into what I might do. Were there museums? Famous attractions? Can’t-miss cultural experiences? I was sure there were—and I knew none of them.

More daunting, I also had no idea how long I would spend there, or whether upon arriving I would want to enjoy the city leisurely or feel anxious to move on. This was less an oversight than a fact of circumstances: this trip has been planned—or not—while I’ve waited to see whether I’ll get a visa to Pakistan, where a friend is getting married in mid-February. I applied for the visa in November. I’m still waiting for a response.

So I found myself, over the sixteen hours it took to get to Santiago via Panama, thinking more deliberately than I had before about how I’d spend the next months, but still with the handicap of not knowing whether I’ll spend one month or three in Chile. I didn’t get far in my thinking on the plane. Mostly, I watched Casablanca.

Things stayed that way for a couple days. I started to develop a plan to go down to Patagonia quickly and plan my next steps from there. So I bought a ticket for Sunday, five days after I arrived, and felt a bit more freedom to explore Santiago in the meantime.

Measured some ways, I barely saw the city. I visited one museum—the striking Museo de la Memoria y los Derechos Humanos, dedicated to the history and legacy of Chile’s 17-year dictatorship—and no other notable sites. I don’t even know what else there is to see.

But measured other ways, I immersed myself. Mostly by using CouchSurfing, of course, I spent time with four different groups of people and met dozens of Chileans (and some foreigners). I stayed with two different CouchSurfing hosts and through the site met another guy, whom I ended up hanging out with three times. I went to two parties, one at a club (where I never go in the U.S.), and another at a hostel. And I spent a very long evening drinking wine and eating hors d’oeuvres at home with one of my hosts, along with seven or eight of his friends and two of mine, other Americans who were also visiting. (I didn’t get to sleep until after 4 that night, because folks were still hanging out on my bed—the living room couch—until 3:30.) Earlier each day, I walked and walked and repeatedly took the Metro to and from neighborhoods I quickly became familiar with.

I loved what I saw of Santiago. It strikes exactly the right balance for me, right now, between familiar and foreign. Once upon a time, I was struck that Bogotá felt very much like New York. Now I’m struck that Santiago feels that way. And what’s familiar about Santiago reminds me of how now, in my mind, Bogotá is a world away from New York.

In the last several years, I’ve lived in or visited a number of large Latin American cities: Bogotá, Buenos Aires, Lima, Mexico City, Santiago. In each, I’ve had an experience that was rooted in not just the place, but also the time, what I was doing, and whom I was with. As the cities begin to blend a little—Santiago feels like a cross between Mexico City and Buenos Aires—they stand apart based on the experiences I had, and the memories I made, in each.

It’s too early to say how I’ll remember Santiago. And I plan to be back in February, before I leave Chile, so I hope to have more experiences there. But, for now, I’m thinking of those five days as a brief, wonderful moment that, like my moments in Mexico City, Buenos Aires, and Bogotá, was, more than anything, about who I was, and who I was with, when I was there.