The next ten to fifteen minutes of memory are a hazy fog for me, filled with flashbacks of Becca and our driver (a man in his fifties with grey hair) belting out Whitney Houston with the windows down and the stereo turned up to a blistering volume while our taxi sped through nighttime Santiago, often attracting the attention of passengers in other cars or people standing on sidewalks. When we finally reached the neighborhood, we drove around for another ten minutes before our driver explained he couldn’t figure out how to get to the hostel; one particular one-way road was throwing him off. He got us as close as he could (about half a block away) and pointed us in the right direction. We grabbed our bags, paid him, thanked him for the entertainment, and he sped off.

We walked down the block, following the street numbers until we got to our hostel. Except there wasn’t a hostel there. We checked and double-checked the street and the house numbers and verified we were in the right place. Yup, right address, no hostel, just a dark building.

Thanks Lonely Planet.

We pulled up the Lonely Planet guide for the neighborhood and located the next hostel on the list. It wasn’t far, so we walked over and found it. And by “it” I mean “another dark building”. We double-checked the street and house numbers again and again; there was nothing resembling a hostel.

Fuck you Lonely Planet.

This particular block had signs for two other hostels, so we tried the first one. No answer. After a few more failed attempts, we left and tried the second hostel. The man who answered the door spoke very little English, but we spoke enough body language to understand he had no beds for the evening.

With the silence of dejection and crankiness fully upon the two of us and the hour growing very late, we started to consider (again) the possibility of being homeless for the night. As our internal monologues became increasingly riddled with obscenities, I decided to look up the third (and last) hostel listed in Lonely Planet. Based on the hostel’s description as a party palace for gap-year kids, we had previously decided to avoid it, but now our hand was being forced, so we started walking.

The hostel (La Casa Roja), thankfully, actually existed. Not only did they have beds for the night, but they had a private room and they would give us a 20% discount if we stayed for three nights. It just so happened that we had exactly three nights left in our trip, so in the interest of getting off the streets and not being grumpy anymore, we signed on.

As we walked to our room and wandered around the hostel, we slowly started to realize what we had stumbled upon. La Casa Roja is located in a former 19th century colonial mansion, complete with multiple courtyards, gardens, a swimming pool, a hot tub, massive ceilings, a huge kitchen and dining room, and at least half a dozen common areas. This was not a hostel, it was an estate. It had grounds. There was a pool house that had been converted into a bar that sold $5 bottles of Chilean wine. And all of this cost us each $20 a night.

OMG THANK YOU LONELY PLANET I LOVE YOU

The next day we slept in after partaking a bit too much of the hostel’s inexpensive selection of wine. We rolled out around lunchtime and walked the neighborhood, finally settling on a place (D’Angelus) to grab some food. We shared some chorrillana, a traditional Chilean/Peruvian dish that is a layered parfait of french fries, beef, and fried eggs. Instead of beef, we had a layer of tasty sauteed veggies. The entire dish was massive and delicious and quite possibly the most perfect hangover food ever.

After lunch, we strolled to Calle Bandera, a street that runs close to Plaza de Armas and is known for having a variety of used and vintage clothing stores. The reason for the shopping was that we wanted to have one bougie night on the trip, so I needed to find some clothes nicer than the ones I had brought. We rummaged through most of the stores for the rest of the afternoon and I ended up buying a sport coat and a few ties; I was hopeful that one of the ties would pair in a not-too-terrible way with the only nice plaid shirt I had brought on the trip.

That evening, we had our bougie night. We went to dinner at an Italian restaurant (Nolita) in Las Condes, a high-end neighborhood that feels like the financial district in San Francisco. In fact, the area is also known as “Sanhattan” (a portmanteau of “Santiago” and “Manhattan”). We knew we were rolling high-class when we opened the menu and realized we were going to have to pay at least $25 for only one bottle of wine. Sheesh, talk about breaking the bank! That said, the meal was worth every penny because we had some phenomenal Italian food. Becca had the blue cheese and goat cheese gnocchi; I tried a bit and I can honestly say it was the best gnocchi I’ve ever had.

After dinner, we walked over to The W Hotel in the hopes of going to their rooftop bar, but our hopes were dashed when we learned it was being renovated. Instead, we settled into their “regular” lounge, which was probably the largest and swankiest hotel lounge I’ve ever seen. We enjoyed some cocktails and pisco while watching a scarf-laden, 20-something DJ spin some tunes while literally lounging on a sofa. We also took the opportunity of actually being dressed nicely to have a faux-model, I’m-too-good-to-look-at-the-camera photo shoot.

The next day was an actual excursion out of the city: a full-day trip to the Andes. We climbed on a coach with about fifty other tourists, rented some snow pants and Wellies, and drove up a steep, switchback-laden road to the top of the mountains. We stopped at a couple ski resorts, had some beers, had some lunch, hiked around a bit, and played in the snow for a few hours. The views and the weather were spectacular.

For our last full night in Santiago, we went back to Bellavista for dinner followed by a visit to a jazz club, something we had been trying to do for the entire trip. As usual, the evening consisted of amazing food and a bottle of wine (which was so exclusive that it didn’t have a label, but rather a vintage written in Sharpie). We spent an unusually long time at dinner because we couldn’t help but chat with the incredibly friendly staff about food, wine, Chile, the States, and traveling. The restaurant (The White Rabbit) was as high-end and organic as anything on Valencia St. in the Mission, but unfortunately they haven’t found their footing yet in Santiago. Here’s hoping that a blog mention and a positive TripAdvisor review will steer some business their way.

Our last day in Chile was spent, appropriately, visiting a couple wineries for tours and tastings. The first was Undurraga, a sprawling estate with fields, fountains, statues, old architecture, massive machinery, and cellars full of wine barrels. The tour was unlike Napa or Sonoma wine “tours” in that this visit included a guide and an actual tour of the grounds, complete with geology, history, and chemistry lessons. It was a gorgeous day out, so no one was complaining about touring a winery and tasting wine in the sunshine. Becca and I each found our soulmates.

The second winery, Santa Rita, had a similar feel. The architecture was reminiscent of Spanish villas, the grounds were sprawling, and the cellars were dark and full of barrels and bottles. Again there was an interesting dichotomy of old buildings and modern technology; bricks, stone, and wood beams peacefully coexisting with stainless steel tanks, digital readouts, and high-output assembly lines. The winery even had a full-fledged museum that was professionally curated and filled with Chilean art and artifacts. Chile takes its wine (and its wineries) very, very seriously. After three weeks of wine-induced bliss, I was ready to trust fall and Chile did not disappoint.

That evening we enjoyed what we could of the city before heading to the airport for our 2:00 AM flight. We stopped at the sushi place next door to the hostel (Platipus) for a bountiful dinner, washed down with some delicious Guayacan beer. With my opportunities for adventure dwindling, I tried one of the veggie rolls with cream cheese and chives and it was some of the best sushi I’ve ever had. Thanks Chile. Thanks for ruining another food group for me.

After dinner, we stopped by D’Angelus again for terremotos, a traditional Chilean cocktail made from pineapple ice cream and pipeño, a wine that’s somewhat similar to white wine. It was a bit too sweet and fruity for me, reminiscent of those frozen drinks you get by the yard in Vegas, but I was glad I tried it at least once. After one last round of pisco sours, we cabbed to the airport and wished Chile a heartfelt and sad goodbye as we started our journey back home.

I plan on writing up one more blog entry with some final thoughts, but for now I’ll conclude by saying my three-week adventure in Chile was a life-affirming trip with a wonderful, close friend. The entire experience was unforgettable and a reminder of why we all work hard, why we all save our money, and why we all bother to get up in the morning. We packed a lot into three weeks, and yet we barely scratched the surface of half the country.

Dare I suggest a southern Chile trip is in our futures? I guess only time will tell.

A short while later, we arrived at our hostel (H Rado Hostel) in Barrio Bellavista, a neighborhood reminiscent of the Mission in San Francisco with its nice restaurants, dive bars, and youngsters. The hostel was certainly on the swankier side with its large wall murals of American icons, a large, sunny common area on the top floor, and a huge roof deck. I’d say it very much epitomizes the idea of a “boutique hostel” and our stay there was very pleasant, especially considering we had a private room with a private bathroom.

After dropping off our stuff and cleaning up a bit, we wandered the neighborhood in search of noms. Much like San Francisco neighborhoods, downtown Santiago neighborhoods are very walkable and you get a great feel of the city and the people simply by walking around. We stumbled upon Patio Bellavista, which Lonely Planet describes as “upmarket eateries and posh souvenir shops ranged around a huge courtyard”. That’s a pretty accurate description and the area does feel a bit different than the rest of Bellavista, but we still found it to be a pleasant part of the neighborhood. If nothing else, it’s a nice respite from the hordes of college students drinking shitty beer and eating hot dogs.

After taking a lap to survey all the options, we settled on a jack-of-all-cuisines restaurant (MosaiCafé) that had some balcony seating with a nice view of Cerro San Cristóbal. Luckily our waiter spoke English and was able to make some suggestions for food, as I was having some trouble finding a good veggie dish (a not uncommon problem in South America). My first meal in Chile was a hot stone bowl filled with veggies and molten cheese, which is as delicious as it sounds. As would become our custom over the course of the trip, Becca and I split a bottle of Chilean red wine at dinner. We thought it apropos to treat ourselves to a very nice Carménère, a grape that was originally French, then thought to have gone extinct, then rediscovered in Chile, and is now decidedly Chilean.

Once we finished dinner, we wandered the neighborhood for a bit, noticing the popularity of the small tables on the sidewalks in front of the bars. Even with the relatively cool weather, most people opted to sit outside (which we noticed in almost all the cities we visited). The bar scene in Bellavista mostly entails sitting at an outside table with a small group of friends and conversing over drinks. And by “drinks”, I mean “cheap beer”. The rule of thumb for drinking in Bellavista is to order cheap beer by the liter, be it Escudo or Cristal (yes, spelled exactly like the expensive champagne). For the sake of doing as the Romans do, we stopped into one of the bars and split a bottle of Cristal ourselves. Our entertainment for the evening was the video jukebox in the bar, which was monopolized by a couple locals who evidently love 80s metal music videos. After getting our fill of Chilean light lager and Guns N’ Roses, we turned in for the evening.

The next morning, we grabbed breakfast at the hostel and then went for a stroll to get a feel for some of the surrounding neighborhoods. We walked through several of the parks next to the Mapocho River, worked our way south through Barrio Providencia, then walked west and ended up in the downtown shopping district around lunchtime. Clearly Chileans enjoy shoe shopping, because I’ve never seen so many shoe stores in one place before (even Becca thought the same). We stopped at a hole-in-the-wall Peruvian place for lunch, which delighted us with bread and (really good!) sauces, a heaping mound of veggie noodles, raspberry juice, and a TV that played only Spanish-language club bangers.

After lunch, we walked to the Plaza de Armas (the main square of any respectable Latin American city) to partake in one of Santiago’s free walking tours, which are offered every day of the week (multiple times a day). They are completely free (other than your tip for the tour guide), are in English, last anywhere from three to four hours, and offer some thorough historical and cultural insights into the more popular parts of the city. Our tour guide was Filipe, who became an inside joke for the rest of the trip because of his unusual, yet delightful personality. He maintained a constantly serious countenance, yet was very pleasant; he was animated and almost theatrical, but in a very controlled and subtle way. (We found out later from his walking tour colleagues in Valparaiso that Filipe is an actor, which explained everything.) The tour was very entertaining and informative and really helped us familiarize ourselves with some of the neighborhoods and some local places we should visit. Filipe insisted on a brief stop in Barrio Lastarria, where we had enough time to sit outside and enjoy some pisco sours.

That night, we went to a more traditional Chilean restaurant in Bellavista (Galindo) that Filipe had recommended on the tour. The food was certainly good (I had the porotos granados, which is a bean and pumpkin stew), but the critically important discovery at this meal was drink-related. As we were ordering, our waitress brought us a separate wine menu and tried to offer an explanation in Spanish (and her limited English), but the language barrier was a bit too high for us to fully understand her. We picked a bottle (Chilean red, of course) and had a quiet, enjoyable meal. As we were settling the bill, she came back to the table with another bottle of wine in a plastic bag. As I looked confusingly over the bill and tried to explain to her that we didn’t order another bottle, she was able to cobble together enough English to explain:

“Two bottles. One for the restaurant, one for the home.”

It turns out that every year for the last twelve years, Chile has organized a rather large-scale promotion whereby participating restaurants and bars (in certain parts of the country) offer a two-for-one deal on reserve bottles of Chilean wine. The first bottle you have with your meal and the second bottle is to be taken home (and cannot be opened in the restaurant). All told, you get two bottles of delicious Chilean wine at a restaurant for about $20.

Game. Changer.

Cue the Kenny Loggins, because we’re heading into the fucking danger zone.

It was around this point (my memory is fuzzy from consuming massive amounts of wine) that Becca and I made a pact to have at least one bottle of wine (between the two of us) every day for the entire trip. Special consideration was given to any restaurant that proudly displayed the reserve wine menu in their window. Sometimes we’d have the second bottle that same night, sometimes we’d take it on the road with us, and sometimes we’d donate it to a particularly nice employee at the hostel we were staying at. In any case, I feel pretty confident that we thoroughly tasted every red wine on that menu.

After dinner, we dropped the wine off at the hostel and went to a small bar (Cuatro & Diez) a couple blocks away. Semi-swanky, candlelit, with live music, it was a great spot to enjoy some cocktails. I tried a Piscola (pisco and cola), a somewhat common local drink, though I wasn’t a huge fan (pisco sours are much better). After a couple drinks, we went back to the hostel and took the aforementioned second bottle of wine up to the massive roof patio (did I mention this was a boutique hostel?) to enjoy the skyline and the sounds of the city.

Fast forward six hours to a healthy hangover at 8:00 in the morning. We grabbed breakfast and then hiked up Cerro San Cristóbal, which was a really nice way to work off the lingering effects of the previous evening. From the top of the hill, you get a breath-taking view of… well, mostly smog. I’m told that after a rainfall, the smog is gone temporarily and the view is spectacular. Nevertheless, we still appreciated the beauty of the view of a sprawling city with the Andes in the background. We enjoyed some quiet meditation time before descending back to Bellavista.

For lunch, we went to the fish market so that Becca could try some seafood soup (another Filipe recommendation). After fighting our way through the gauntlet of outgoing (read: annoying) restaurant hosts, we settled on a small, unassuming spot that was mostly filled with locals eating lunch by themselves. After explaining to our waitress that I was vegetarian, she responded simply with “Ensalada.” and reached for my menu. I resigned myself to eating bread, sauce, and rabbit food (Becca’s term for my salad that looked like a plate of condiments) while Becca enjoyed her cauldron of seafood.

After fighting through the restaurant gauntlet on the way out, we walked over to Cerro Santa Lucía, a small hill in the middle of the city with facades, stairways, patios, fountains, and really great views. We walked around the grounds for a while, snapping photos and enjoying the weather, until it was nap o’clock. With lack of sleep, a food coma, and sunny weather all conspiring against us, we laid down on the grass (amongst the usual collection of Chilean teenage couples) and checked out for a while.

That evening, we hit up a nice Italian spot in Lastarria for dinner, then wandered around Bellavista for a bit before settling on a karaoke bar. Surprisingly, a good amount of the music was English-language and a few of the singers really killed it.

The next morning, we checked out and took the Metro (Santiago’s light rail) to the bus depot. Another commuter (who spoke English) offered his help when he saw a couple gringos unfamiliar with how the Metro system worked. (It was one of many acts of kindness we encountered during our trip.) Once at the bus depot, we hopped on a coach to Valparaiso, a nearby coastal city that we had heard a lot about while in Santiago. This was probably the first point at which our itinerary diverged from our pre-trip plans and, unbeknownst to us at the time, would eventually lead to a completely different trip than we had initially imagined.