Picture this: it's 8:30 in the morning on the coast of Chile, you're standing in a hotel hallway in your sandals, and your friend — let's call her Sylvia — comes walking back from the vending machine balancing three paper cups like she's bringing peace offerings. Her Spanish is genuinely good. The vending machine, however, is not. One cup is hot water with sugar. One cup is, and I'm being charitable, "loosely a coffee." The third is the closest thing to a café latte you'll get from a hallway machine in Valparaíso.
We split them. We laughed. We ordered Ubers. The day was already off to a strong start.
This is the story of two days driving down to the Pacific from Santiago — Valparaíso, Viña del Mar, a winery in the hills, a rotating restaurant, a cold plunge I never asked for, and an Uber driver who genuinely made me believe in Formula 1.
What's coming: the most artsy two cities in South America, the Croatian who built a whole architectural sampler in 1916, three pizzas at 11:30 at night, and the moment Sylvia got us through Boxing Day still wearing yesterday's clothes — because (callback alert) our suitcases were still touring South America without us.
Two Cannons, a Tour Guide, and the Quietest Morning of My Life
Our meeting point was downtown Valparaíso, by two old cannons up near the port. We Ubered in from Viña del Mar — and here's the first thing nobody tells you about these cities: at 9:30 in the morning, they are empty. Like, post-credits empty. A few cars. Almost no foot traffic. I could have walked down the middle of the street and nobody would have noticed.
By 12:30, the place is a different city. Cars everywhere. People everywhere. Music, food carts, energy. By 6 p.m. the live music starts, and apparently it doesn't really stop until midnight. Greater Valparaíso–Viña is a little over a million people and they all seem to clock in around lunch.
Do nothing before noon. Sleep in, drink coffee slowly, walk the murals at dawn if you must — but the cities don't really start until lunchtime, and they don't really stop until midnight.
We met our guide promptly at the cannons, joined a small group from the UK, and started the tour. He was a one-man Wikipedia: history of the indigenous peoples of Chile, history of the port, which buildings were original, which had burned and been rebuilt, which had simply vanished. Dates, names, anecdotes. He pointed out where 19th-century shipping had reshaped the city, and where the 21st century had reshaped it again.
Then he mentioned, casually, that he'd built the app for the funicular himself.
Excuse me?
"He was originally from Cuba, he'd lived in the city now for years, knew everyone, and somewhere between giving tours and raising kids he'd taught himself to code an app for one of the city's oldest landmarks. Behind every great tour guide is somebody who is also five other people."
Up the Funicular, Into the Murals
A few minutes on the funicular and we were at the top — those classic Valparaíso vistas, the ones you've seen on Instagram, with the cerros stacked up against the bay. They earn the hype.
But the real surprise was what was on the way back down.
One of the dozens of murals lining the streets above the port. Walk these streets at 9 a.m. and 6 p.m. — same walls, two different cities.
Valparaíso is a city of murals. Not "a few murals." A city. Entire buildings — exterior walls, stairwells, alleys, doorframes — covered in art. Some of it political (yes, including the United States, yes, including Donald Trump), some of it abstract, some of it the history of Chile itself. The guide walked us through the layers. Which mural is recent. Which is older. What this one is reacting to. What that artist meant by the colour palette. We turned a corner and there was another. Another corner, another one. It does not stop.
If you go: walk these streets in the morning while it's still quiet, then walk them again at 6 p.m. when the live music kicks in. Different city. Same walls.
Paseo Yugoslavo: The Croatian Who Built a Whole Style Sampler
This is the part of the tour where my Eastern-European-curious self really woke up.
Palacio Baburizza, 1916 — built by a Croatian philanthropist who couldn't pick just one architectural style.
The guide led us to Paseo Yugoslavo — a viewpoint named after the wave of Yugoslav (mostly Croatian) immigrants who shaped this part of the city in the early 1900s. The centerpiece is the Palacio Baburizza, built in 1916 by a Croatian immigrant philanthropist named Pascual Baburizza. He apparently could not pick a single architectural style. So he just used several. Art Nouveau elements here, Italianate touches there, a bit of everything stitched together into one strangely cohesive house. It's now an art museum.
(I have written before about driving through Croatia in a rented VW. There's something about coming all the way to the Pacific coast of South America and finding a Croatian house staring back at you. The world is smaller than you think.)
If you have an hour, go inside. The art is solid. The building itself is the show.
Boxing Day in Valparaíso (Sponsored by LATAM)
Pop quiz: what do you do on a beautiful Boxing Day in Chile when you have no shorts, no T-shirts, no swim trunks, and no idea where your luggage is?
You go to the mall.
If you've been reading along, you'll know the long version of this story is in my lost luggage post — the one where WestJet, LATAM, and my credit card collectively took me to school. Short version for new readers: our three suitcases had been doing their own tour of Mexico and parts unknown for several days at this point, and we were still in yesterday's clothes.
So we split the group. Half of us went to the museums and the murals. The other half — me, Irena, and Sylvia — went to the mall to fight Boxing Day crowds for shorts and shirts. Pickings were slim. Lineups were long. Spanish was being shouted over loudspeakers in a way that made me think they were calling our names again, like Cancún. They weren't. We were just three Canadians blinking at the rack of swim shorts.
We grabbed completos on the way back — the Chilean hot dog. Avocado, mayo, tomato, mustard, the works. Imagine a Canadian gas-station hot dog if it had been raised abroad and become a much more interesting person. Real food. Cheap. Excellent.
The other half of the group reported back from the streets: by 6 p.m., live music, dancers, vendors, the whole city humming. They didn't want to leave. They came back to the hotel anyway, because dinner was the next plan and we had bigger ambitions.
Toes in the Pacific (And Why I Regret Them)
We had picked a restaurant the previous night with a beautiful view down to the rocks and the surf. Tonight's plan: same restaurant, but first — dip our feet in the Pacific. Right there. Below the patio.
The point at which I learned what the Humboldt Current does to a Canadian's circulation.
The water was cold. Not Mediterranean cold. Not "oh that's bracing" cold. Rocky Mountain river cold. The kind of cold that resets your nervous system. The kind of cold where you stand there and slowly understand why every stone on this beach is so smooth: the ocean has been quietly killing things for millennia.
The kids — bless them — went swimming. Actual swimming. The three of us older, wiser, and arguably saner adults went in up to our ankles and then stood very still trying to remember what warmth had felt like. Three days later in Santiago, I was still pretty sure my left big toe was somewhere off the coast of Antofagasta.
If you're going to dip your toes in the Pacific off Viña del Mar, dip them. Then leave. Do not stand there bargaining with yourself about going deeper. The Humboldt Current is undefeated.
The Uber F1 Driver Who Saved Pizza Night
After dinner, the bay started lighting up.
A massive crowd was gathering along the coastal road — locals, families, kids on shoulders, blankets out — for the holiday-week fireworks display. We had a plan: hit a pizza place we'd spotted earlier, then walk it off. We ordered an Uber. The app said: 5 minutes.
Then 5 minutes.
Then 5 minutes.
What should have been a 12-minute drive turned into 45, because the entire population of Valparaíso and Viña del Mar had apparently agreed on the same coastal viewing spot and the road was a single, glittering, unmoving string of taillights.
This is where our driver became a hero.
In our combined three words of Spanish, we somehow communicated the idea of please get off the ocean drive and take us up into the hills. He nodded once. And then he drove.
Hairpin lefts. Hairpin rights. Up steep neighbourhood streets that I was pretty sure weren't roads. He shaved 11 minutes off the GPS estimate. I want to be clear: this man was not reckless. He was precise. Every corner taken at exactly the speed that wouldn't tip the car or cost him his five-star rating. He was a professional.
"It was the best driving I've watched from a passenger seat in years. He earned the tip, the rating, and a lasting place in this blog."
We rolled into the pizza place at 11:30 p.m. Three large pizzas. Almost finished them. The crowds were thinning. The fireworks had ended. We walked, took a much calmer Uber home, and slept like people who had earned it.
Tomorrow: wineries.
Day Two: "Today Is Winery Day"
Sylvia's words. Said with the energy of someone who had been waiting all trip. We packed up, said goodbye to our balcony view of the Pacific (still cold, still beautiful, still holding my left toe somewhere in its depths), and waited streetside for our driver.
He showed up at 9 a.m. in a minivan, a friendly guy who immediately understood the assignment.
The morning's first task was breakfast. Sylvia had a plan: eat in the van, save time, hit the road. We just needed something to grab. Easy.
It was not easy.
Nothing — and I mean nothing — was open near our hotel that early. Not the bakery. Not the corner café. Not the place that promised a croissant. The driver, who had clearly seen this movie before, gently broke the news: "There's a McDonald's at the gas station on the way out of town."
So our first sit-down — sit-van — meal in Chile was a McDonald's hash brown.
There is a strange kind of comfort in this fact. There is also a strange kind of sadness. I'm not going to dwell on it. The hash browns were correct.
The drive was beautiful. Eucalyptus and dry hills, the kind of light you only get on a coast that's still warming up for the day. About an hour later we turned off onto a dirt road and rolled up to the winery.
The Wine Tasting (and the Cheese Eclipse)
Ranch-style entrance. Big wooden gate. We piled out into the heat — four young adults, three older adults, all of us hungry, all of us ready.
The winery offered two tiers: a guided tour with a sommelier through the cellar, plus the tasting; or just the tasting on its own, with cards that explained each wine, where the grapes had come from, and what we were drinking. The first option was substantially more expensive.
We are not a substantially-more-expensive-by-default family. We chose the cards.
The cheese eclipse, Casablanca Valley edition. Sarajevo had meat. This had brie.
This was the right call. The wines were beautiful. We read, we sniffed, we sipped, we discussed, we felt very mature. We added three platters of charcuterie and cheese, and those — those were a meat-and-cheese eclipse. (If you've read my Sarajevo post, you know I have history with eclipses on plates.) Cured meats stacked with manchego, blue cheese, jamón, fruit, breads, oils. We took our time. We bought several bottles to bring home — including ones that aren't sold in Canada, which made it official: this was a serious tasting now.
And then, in a development that I attribute entirely to the wine and not at all to my charm, the staff offered to take us down into the cellar anyway. The full tour. For free. We accepted, possibly while giggling.
"Tipsy in a wine cellar, surrounded by oak barrels twice as old as our kids, learning about Chilean Carmenère from someone who clearly loved her job — that was the moment I understood why people make wine pilgrimages."
Highly recommended. With kids in the group, even more so — they got to see how a real winery works without the parents losing patience over a two-hour formal tour.
Santiago, the 360° Restaurant, and a Verdict on Wine Versus Views
Back in Santiago, traffic had thickened — Christmas was officially over and the city was waking up. We made it to our hotel just in time for check-in. Beautiful place. Big rooms. Clean lines. A pool deck with the kind of evening light that makes you want to cancel dinner plans.
We didn't cancel. We had one item left on the day's list: a rotating restaurant with a 360-degree view of Santiago.
The view I was definitely going to remember. Then dinner happened.
A short 10-minute walk from the hotel got us there. The views, in fairness, were genuinely lovely — mountains in one direction, city sprawl in another, the slow rotation giving you a new angle every time you looked up from your plate.
And here's where I have to be honest, because Behind The Shades doesn't lie:
After the second glass of wine, I cared substantially less about the view.
Do the rotating-restaurant places first. Wine after. The view will not improve as the evening goes on, but your appreciation of it absolutely will diminish. Lesson learned.
The food was solid. Service was friendly. The view was the reason to be there. The wine was the reason I'd already kind of forgotten about it. There's a metaphor about life in here somewhere and I'm too full to find it.
The Pool, the Bottle, and the Quiet Win
After dinner we wandered the streets looking for ice cream — found some, ate it, walked the city, beautiful evening — and made it back to the hotel. The kids announced they were done. They retreated to their rooms.
The three adults did the math: there's a bar, there's an outdoor pool, there are loungers, and there is no plane to catch in the morning. We ordered a bottle of wine. We sat by the water. We did absolutely nothing of consequence and it was the best part of the day.
You may have noticed wine plays a leading role in this episode. I'm not going to apologize for that. Chile has earned it.
The Honest Take
Valparaíso and Viña del Mar are a two-day stop, easy. The murals are world-class. Paseo Yugoslavo is one of those weird, wonderful European footprints in a place you didn't expect it. The food on the street — completos especially — is cheap and excellent. And the Casablanca Valley wineries on the way back to Santiago are absolutely worth the half-day detour.
On the flip side: the Pacific here is cold, restaurants don't open early, and if your luggage is missing on Boxing Day you will be shopping a half-empty Chilean mall instead of seeing the city. Also, the rotating restaurant in Santiago is best enjoyed before, not after, several glasses of Chilean red.
Highlights
- Valparaíso's mural streets — entire neighbourhoods turned into open-air galleries.
- The funicular ride — short, scenic, and apparently coded by our tour guide.
- Paseo Yugoslavo and Palacio Baburizza — Croatian Art Nouveau on the Pacific, of all places.
- The Casablanca Valley winery — DIY tasting plus charcuterie plus a free cellar tour we did not earn but happily accepted.
- The Uber F1 driver — 11 minutes shaved off the route, zero white-knuckles, all skill.
- Three pizzas at 11:30 p.m. — the universal language of "we made it."
Would I go back? Yes — but with shorts that I packed myself, the rotating restaurant booked for before the wine tasting, and at least one extra night so I'm not driving past Casablanca Valley wineries with regret. Two days is enough to get the flavour. Three would let you actually sit with it.
Coming soon: Behind The Shades — Cancún, Girls' Getaway Edition. Irena's trip, Irena's rules. A different pair of shades entirely. Less me complaining about cold water and rotating restaurants. More cocktails. Stay tuned.
And — Sylvia, if you're reading this — the vending machine still owes us one real coffee.
