The End of Big City Season: Valparaiso and Santiago

Nothing has changed taking overnight buses. I never sleep well, and I always get the seat next to the guy yelling on his cell phone keeping the baby one seat in front of me screaming. That said, I take them every chance I can, and love walking into a new city at dawn. Such was my thought process arriving to the amazing city of Valparaiso. However, when I stepped off the bus at 6:30AM Saturday morning, it might as well have been midnight. It was pitch black, misting, and the streets near the bus station were deserted. My destination was a hostel named La Esquina on a hill named Cerro Alegre (translation: happy hill). If you were wondering why I picked that hostel, my disposition was happy and I like corner lots (La Esquina). Yes, it is very scientific.

At night, because in Valparaiso 7:00am was still night, the streets, empty except for a graffiti speckled grunge, caused a heightened sense of caution. As I approached the base of the hostel’s hill, creatures of the night appeared. The street was filled with people still awake and partying. I waded through the wave of borrachos (drunks) with all of my things, and began the walk up. As I ascended, the graffiti went from sporadic to covering everything, but by the time I reached the top it was quiet. Where was the charm that everyone raved about when they spoke of Valparaiso? Where was I, and what time was sunrise?

Álvaro, the long haired owner of La Esquina, opened the door of the Victorian style building, and welcomed me in. I could tell I woke him up, but he was very hospitable. I grabbed a copy of Lonely Planet from the hostel book share and read about Chilean Patagonia for a couple of hours. When the sun finally rose, around 8:30am, the mood of everything changed. I made my way out of the hostel and hit the streets. The top of the hill was lined with cafes and narrow staircase alleyways branching into labyrinths of unique storefronts and homes. I quickly understood why people loved this place, and my opinion was quickly falling in line.

Since Valparaiso was a bigger city, I followed my big city routine and caught the 10:00am walking tour. Comfortable with Spanish, I decided to up the ante and took a Spanish guide. On the tour, I immediately met a Portuguese woman named Caterina who became one of my favorite memories from Valparaiso. We walked all over the charming city filled with hills in addition to Cerro Alegre, looked out over the Pacific, admired the graffiti murals covering the buildings, and followed the secret boardwalks and alleys everywhere. A port of Pancho San Francisco, there was a similarity to the artsy San Francisco, USA of old. The tour finished in an iconic multi-purpose building in the city center. An older woman stared from a balcony above as the guide described the different faces the city could take. She showed many of her own as he described the good and bad.











Following the tour, we had lunch at a restaurant around the corner that I later discovered was one of Anthony Bourdain’s recommendations. I love when life leads to random surprises. On the subject of surprises, we enjoyed the morning tour so much that we decided to join an afternoon tour with the same company. When Caterina and I joined our second group, a hand grabbed me on the shoulder. An Italian/Swiss couple that I had hiked with two months prior in Northern Ecuador was on the the same tour! We hugged, had a lot of laughs, and discussed their experience spending six weeks in a van in Chilean and Argentinian Patagonia. Needless to say, I had tons of questions and was ecstatic to run into them again. The afternoon tour was great, but my side conversations were the focal point.

After our second tour, Caterina and I broke away and enjoyed a happy hour complete with Cerveza Austral, the mainstream Chilean beer, and hours of conversation. To my dismay, she had a flight leaving from Santiago in the morning, and had to get back. Traveling has led me to meet incredible people, but because of life circumstance those relationships are short, intense, and bound to end before they’re ready. This was no exception. At 8:30PM I walked her to a bus headed towards Santiago, left her with a traveler’s goodbye, and hoped that the goodbye wouldn’t be the last.

A thundering snore rattled the screws in my metal bed frame causing me to groggily open my eyes. After ensuring that I wasn’t under attack, I located the source of the disturbance. My neighbors were a couple of Austrians whom I had shared more than one beer with the night before following Caterina’s departure. One was about 6’4 with a beard and long hair, and the other, his friend, was a blonde haired woman covered in tattoos who I assume could have snapped me in half if she so decided. Needing to escape the assault, I slowly crawled out of the room.

I walked around the corner to an amazing cafe and planned to spend the day as a Valparaisian writing and working on photography. To my excitement, after a few hours, I received a message from the Italian/Swiss couple, and they joined me at the cafe. They laid out maps of their journey, and we went over their favorite sites in Patagonia. As a deja vu, my friends were headed out on a bus that evening to Santiago, and after a few hours they departed. The rest of my afternoon encompassed eating empanadas and trying a dessert cookie called an alfajor. Alfajores are two sugar cookies sandwiching a sweet filling called dulce de leche. After a bit more writing, I headed to bed and decided to make my way to Santiago the following afternoon. I loved Valparaiso, but remained focused on making progress to my true destination: Patagonia.






With a much smoother and quieter wake up than the previous morning, I packed and got ready to head to Santiago. Before leaving, I ate breakfast at the hostel and assessed how long it would take me to travel to “the end of the world Patagonia,” otherwise known as Ushuaia, Argentina. With a plan to use a mixture of busses, hitchhiking, and walking to reach my selected destinations, the amount of time it would take to make it all the way south was unacceptable with the changing seasons. I would never make it before the heart of winter, and Patagonia was no place I wanted to be camping, exploring, and hitchhiking mid-winter.

While evaluating my options, I decided to look up flights to the most Southern Chilean cities: Puerto Natales and Punta Arenas. I couldn’t believe what I found: there was a flight leaving to Puerto Natales from Santiago on the following Saturday for $45. I booked without hesitation and rerouted my plan to travel up Argentina and Chile instead of down. With a new plan, I called my friend Dan whom I had met in San Pedro de Atacama, and he invited me to stay with his wife Chiro and him in Santiago. After one final walk around Valparaiso, and a goodbye to Alvaro, I walked down Happy Hill for the last time and caught the 1.5 hour bus East to Santiago.
I boarded the metro immediately after stepping off the bus in Santiago. It had been so long since I was in a big city with comparable infrastructure. Everything was moving so fast! Here I was on the train, with all of my gear, surrounded by chic, hip, students and adults, and professionals on their way to and from the office. I didn’t exactly fit in. Dan and Chiro lived in an upscale neighborhood of Santiago named Providencia, and I stopped a few stops early on the metro to walk 45 minutes to their apartment and get a feel for the city. It was great to see them when I arrived, and it felt like running into old friends. They truly were amazingly generous and kind people. For the next week in Santiago, I enjoyed their company and many amazing dinners cooked by Chiro. It took me travelling to South America to eat incredible Indian food, and eat it properly: with my hands.

Santiago ended up being the city where I reconnected with the most travelers I met on my journey with intent. In addition to spending time with Dan and Chiro, I also messaged Viviana, the woman who I previously met in the city of La Serena. My first morning in Santiago I was up, ready for a walking tour, and Vivi had told the other travelers from our group in La Serena to join me. As I waited for the metro to the central plaza de armas, something that has started to become expected happened: a hand touched me on the shoulder. A couple of German women that were part of the hostel group were waiting at the same time, and we joined the tour together. The tour was average, and I wasn’t in awe from any of the stops, but what was fun was hanging with our international group of German, Swiss, Colombian, Brazilian, and of course the good old USA.

Following the tour, Viví joined us and we had ice cream at one of the “top 25 ice cream places in the world.” Emporio La Rosa lived up to the hype, and the cold sweet ice cream on the warm day after walking all morning, made for a perfect setting. This was the last meetup of the group from Northern Chile, but we continued to stay in touch.


The next few days in Chile were relatively calm in preparation for my upcoming flight to Patagonia. Some great food experiences were had at La Vega Market and Lomit’s Sandwiches. La Vega was a unique market that was large in scale and differed from many of the other South American markets. The influence of European culture was evident in the prepared salamis, olives, and overall display of the food. Like Chicagoans with pizza or San Franciscans with burritos, Santiagans have a similar obsession with allegiances to their favorite chacarero sandwich restaurants. Thanks to Vivian, mine was now Lomit’s. The balance and choice of meat, spice, large sandwich size, and Kaiser bun made for a good meal to prepare for two months climbing mountains.

Before I knew it, six days of great company, Indian food, and exploring Santiago had passed. Though it was sad saying goodbye to Dan, Chiro, and Viviana, I had a feeling I would see them again, and the excitement of finally getting to Patagonia was consuming. I usually don’t sleep before treks begin, but Friday night before my Saturday morning flight was a whole new level of being awake. I couldn’t begin to fathom what I had in store for me.

The alarm sounded at 6:30AM signaling that it was time for me to get moving to catch my 10:56AM flight. I had packed everything the night before, so all that was left was giving a once over to Dan and Chiro’s apartment and walking to the metro station. Fully packed with a substantial amount of food, everything was heavy, and I felt four times the size of anyone else on the train; in reality, I was. Due to the remoteness and tourist base in Patagonia, everything is more expensive. I brought as much as I could carry. The train out to Pajaritos station went much faster than the ride in. Once at the station, I grabbed a quick empanada and caught the bus to the airport. Again, I stood in the doorwell for the 30 minute ride to the airport strapped full of my things. I accepted the looks of bewilderment from my fellow riders with their simple roller suitcases, and answered where I was headed from the multiple people who asked

At the airport, the line of people waiting to board the flight was a spectacle. There was more English than Spanish being spoken, and there was a clear divide of local Chileans who were nicely dressed and the hoard of hikers from around the globe. No matter young or old, or alone or in a group, everyone’s faces showed excitement. I quietly observed and wondered how crowded the trails would be if plane loads like this one were headed South. Boarding the plane from the ground, I caught a glimpse of the baggage being loaded onto the plane. It looked like a manufacturing line as every item being loaded below was a multi-day trekking backpack. Not having slept the night before, I quickly dozed off in my seat.

I woke up in time to see us flying over the Patagonian ice-fields, and goosebumps came over my whole body. The Chilean woman sitting next to me snapped pictures, and I excitedly talked with her about where we were headed. A thud and a short stop later and we were on the ground. I sprung out of my seat, grabbed my small backpack and waited for the rear plane doors to open. When I walked through them, a blast of fresh cool air hit me in the face, and in the distance the single landing strip pointed towards an immense snow capped mountain range. I was smiling and couldn’t stop. The simple landing strip had a sign that said “Bienvenidos a Puerto Natales.” For me, it was bienvenidos to the land of exploration. Bienvenidos to my adventure and the wild.


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