Santiago wrap up:                          thoughts on month 2

This was such a strange month. Reflecting on it, I’m not sure what to attribute that to. Perhaps the honeymoon period of Remote Year (RY) is wearing off – we’re all settling in a bit and remembering that this is real life and you can’t burn the candle at both ends forever. Perhaps it was because this is a new city for RY – we were only the third (and fourth, more on that later) group to come through Santiago, and it showed. There were definitely some kinks to be worked out regarding the city experience. Perhaps it was because we were sharing the city with another group – we were in Santiago with another RY group who was in their first month and that really changed the dynamic. Maybe it was because so many of us had our own spaces. Maybe it was because the workplace wasn’t our favorite. Maybe it was because everything was obscenely expensive, and mostly unremarkable. Or maybe it was the city itself – it was cold and unwelcoming to visitors. Whatever the reason, this month just felt off.

I liked Santiago more than most of my group did. I like big cities and this felt like a proper big city. I also appreciated that, unlike Lima, it was not humid. In fact, being cold nearly all of the time (thanks to my one and only jacket being stolen in Cusco) was a welcome change. I tried to give Santiago a chance, I really did. I sought out wine bars, ventured out for dates in other neighborhoods, and saw the major tourist sights. But it never grew on me.

After side-tripping to Buenos Aires, Argentina and Uruguay for a weekend, I couldn’t help but wonder why Remote Year left Argentina for Chile. I would much have spent a month amongst the beauty of “the Paris of South America.” The great thing about RY though is that they collect feedback every month, and they act on it. I found myself thinking of those first few RY groups — I heard about RY about 6 months into their existence and I knew it would be a couple of years before I could make it happen, and that was so disappointing at the time. But I am benefiting from the experience of 20 something odd groups, and things are mostly dialed in at this point.

Sharing the city with another RY group

This month there were two RY groups in Santiago. We were in month two (of twelve), and the other group was in month one (of four). I’m not sure if this dynamic would have been drastically different if either or both groups were farther into their programs, but I really didn’t enjoy having multiple groups. I think it overwhelmed our new city team, especially considering how many people had issues with pickpocketing, theft, and mugging (which required the assistance of the city team). I also felt bad for the other group who was in their first month – it really impacted (seemingly) their bonding with each other.

It was fascinating to see how each group seemed to attract a specific kind of person. Our groups seemed vastly different, and it’s amazing to me that people seemingly self-selected into these groups. I do think that the 12 vs 4 month duration of the program played a huge part in why our groups felt so different. I believe there’s a different mindset when you’re gone for 12 months. So many of us completely uprooted our lives: sold belongings, got rid of cars and apartments, and broke up with significant others. In short, we’re all in on this experience, and we recognize that this crazy travel family is all we have for the next year. Speaking of month 13 (aka after the program ends) is a big no-no in our crew – no one wants to think about what that means or what that looks like – and we certainly don’t want to think about saying goodbye to our tramily (and mind you, we were strangers 8 weeks ago). The 4 month crew spoke often of “when I get back home,” and many of them still had lives back home – apartments, cars, pets, and social lives were all waiting for their return. It brought a different feel to the group for sure .

This month we also shared the city with two citizens (remotes who have completed their 12 month programs), and are now here on their own. They joined a few of our events (they knew about them thanks to the Slack connection you have for life). Additionally, we had one of the RY staff in town with us, Travis, who is the person in charge of all things community related. He lead the 3rd ever cohort, so it was super fun connecting with him and hearing how RY has grown, changed, and improved over the years.

Overall, while it was fun to meet another group and have the experience of sharing a city, I am happy to have the city to ourselves again in Medellin.

Safety in Santiago

I feel compelled to bring this up again. We were the third/fourth groups to live in Santiago with Remote Year. I didn’t follow the experiences of the first group, but I did follow the second group closely. They had a lot of issues with safety, as did we. I can’t begrudge RY for trying to be cost efficient – they are a business and they have to make money. But at this point, it’s a trend that well over 10% of the group is going to experience some sort of theft or mugging, and that starts to make me question the logic in being here. It’s a rough part of town, and Santiago certainly isn’t all like that. Furthermore, we stand out for a lot of reasons – making us easy targets. It’s hard to love a city you never once felt safe in. It’s exhausting to constantly consider whether your purse is locked, if it is safe to even wait for an uber (much less walk anywhere), to worry everyone passing on a bike will rip your phone from your hands.

Saying goodbye

This month also saw our first Tramily goodbye. One of our remotes went home, and I think a lot of the group missed getting to say goodbye. It had only been 6 weeks, but I think many of us feel like we’ve known each other much longer, and saying goodbye to family is always tough! This isn’t unusual – most groups see around 10-30% of their cohort leave before the end of the year, for a variety of reasons: some because of an opportunity they couldn’t pass up, some for family reasons, and some just decide it isn’t for them. I know it won’t be our last goodbye this year, but it’s already hard to imagine saying goodbye to these people in 10 months, much less any sooner.

On a happier note, here’s a few of my favorites:

Wine spot: Vinocracia – it’s hard to beat glasses of wine for $1000 CLP ($1.50 USD), especially when they are so drinkable!

Dinner: Santa Brasa – I don’t eat a ton of meat, but I devoured every bite of that massive filet mignon. And don’t even get me started on the chocolate lava cake we had for dessert.

Nail place: Mano a Mano. Although I paid US prices, it was clean, had a large selection of colors, and the owner spoke English. I didn’t enjoy the pedicure here though.

Coffee: Café Monstrum. I found this based on a review from an Aussie, who was touting the coffee quality (and you know Aussies know their coffee!).

Café to work from: Wonderland Café – a cute Alice in Wonderland themed café with good internet and a couple of power outlets.

Fun fact about Chile: they have daylight savings time sometimes. Not every year, and not with any set cadence. And it does not match the weekend any other countries have DST. Good luck figuring out what time it is in relation to anywhere else in the world!


  • Seeing Tiesto at Lollapalooza
  • Singing along to “Wonderwall” at the top of our lungs in the middle of the night – and having security threaten us…twice!
  • Dance parties on the bus during our Wine Tour.
  • 5 bottles of tequila at the club, 14 people, and $25 per person.
  • “Do you want me to take your pants off too?” “Nooooooooo!” -Joe
  • Singing “Summer Nights” during karaoke at Quinto Cheers
  • The daily cannon explosion at noon (wait, favorite memory…?)
  • Passover Seder
  • Beating the Uroboros in a nail-biter ending at the Santiago Farewell Game Night showdown!

Final thoughts

I spent a lot of time wondering why RY left Buenos Aires for Santiago. However, I am grateful for the opportunity to see Chile. Argentina was a destination high on my list – I would have gone there either way, but I’m not sure I would have made an effort to see Santiago (or Vina del Mar, Valpraiso, or one of it’s many other cute little towns) had we been in BA for the month. Santiago wasn’t terrible – I didn’t hate it and we definitely made some good memories here.

But onwards and upwards – I’m looking forward to Medellin!