I visited Santiago, Chile for the first time twelve years ago as the gateway to my first South American adventure. American Airlines was running a promotion that gave a free international round-trip ticket anywhere in the world that the airline flew in exchange for buying a round-trip ticket to Florida and California. I did a weekend trip with my roommate Nick to Fort Lauderdale and then I must have visited my sister in California (because she’s the only person I knew in California at the time). When redeeming, I chose the destination that American flew furthest away from Boston, Massachusetts where I was living which turned out to be Santiago.
I spent a few days exploring Santiago, Valparaiso, Vina del Mar and the Cajon del Maipo — of which Santiago I found the least interesting; I didn’t see much personality in it. I continued elsewhere throughout Chile and Argentina having decided there was nothing I need come back for in Santiago. I did return though and this time around, though it was just for 11 days, it felt like a lot longer. Nothing much has changed including my rather offensive opinion that Santiago doesn’t have much going for it from a travelling gringo perspective. It’s easy and comfortable to live in and has modern amenities but the food quality, personality of the city itself as well as cultural intrigue — not much going.
A highlight of my time in Santiago not surprisingly involved departing from it to venture to a vineyard with a pack of my friends. We toured the Montes Winery and afterwards I photographed my friends as models for a new startup (started by one of them), Wild Heart. And the more I reflect back on my time in Santiago the more fun it was — having dinner and drinks with friends, working in a cool industrial office space and generally living a quality daily routine instead of a vacationer’s. So now should I be judging destinations from this perspective? If so that makes so many places that previously were not, now worthwhile. Such existentialist befuddlement… I believe I have turned a corner.