My Home, Valparaiso, Chile

Let’s get something out of the way
This might be the hardest blog I’ve ever had to write. I’m holed up in a hotel room in Ireland just to find the distance I need to talk about this city. Not a vacation. Just space. That’s how much Valparaíso gets under your skin.

How it started
I grew up in New York, but Valparaíso grabbed me at 14 and never let go. I ended up living there for nearly 20 years. And back then? It wasn’t even on the map. It was raw, unfiltered, and known only by those who knew how to find it. Tourism wasn’t what it is today, and most restaurants trying to adapt to a "world standard" have completely missed the point.

Valpo’s not here to impress you
When you go to Valparaíso, you’re on your own. It’s like Medellín, Barcelona, Marseille, or East LA—a place with pride, grit, and culture that doesn’t care what you think of it. You don’t walk around flashing a gold chain. If you don’t have at least some street smarts, the city will eat you alive. And yet, if you let it, it’ll be one of the most beautiful experiences you’ll ever have.

It’s not supposed to be safe
Think of Rio de Janeiro. Sketchy? Sure. Still one of the most visited cities in South America. Why? Because people adapt. They move smart, soak in the chaos, and leave with stories. That’s Valparaíso too.

It’s not just a port
It’s 45 hills of organized disorganization, alleyways that turn into staircases, murals that melt off crumbling walls, trolleybuses from the 1940s still dragging their wheels downtown, and neighborhoods stitched together by stubbornness and soul. It’s gritty, loud, spontaneous, and somehow elegant in its decay.

Who this city is for
If you like order, predictability, and spotless sidewalks, Valpo’s not your scene. But if you travel to feel something—if you're into color, noise, art, seafood, working ports, spontaneous dogs, and people who’ll give you their opinion whether you asked or not—this place is it. You don’t come here for perfection. You come here because you’re okay with wandering uphill with no map, finding poetry in the gutter, and watching a guy freestyle next to a crumbling colonial building that hasn’t seen a paint job in 60 years.

Moving smart
Is Valparaíso safe? Depends on how you move. Don’t flash your phone. Don’t wander into alleys at 1 a.m. like you’re invincible. Wear simple clothes. Carry what you need. Look around. Listen to the locals—they’ll tell you where not to go. Be cool, and the city will leave you alone. Try to be flashy, and the city will remind you you’re in South America.

Food worth walking for
Eat local, eat fresh, and never underestimate a street stand. A Completo and a Sopaipilla can feed you better than a $30 plate at a tourist café. Grab a quick bite at La Riviera, something lighter at Melbourne Café or Panini Café, or sit down for a more crafted meal at La Caperucita y el Lobo or María María. If you're in the mood for dinner with depth, Moneda de Oro delivers—get the calugas de pescado with a cold lager or a crisp white wine.
Café Waddington on Avenida Gran Bretaña is great for a quiet tea or vegan sandwich, especially if you want to admire the old Victorian facades. 

Where to base yourself
If you’re staying the night, Cerro Alegre or Cerro Concepción is where the pulse of the city lives. Boutique hotels, hostels, and guesthouses are scattered throughout colorful streets and alleyways, each with their own view, their own version of the story.

Getting around
Getting around is its own adventure. Uber works fine, colectivos will zip you around for cheap, and the old trolleybuses downtown are worth the ride just for the experience. Buses go pretty much anywhere you need, just ask around if you’re not sure. And no—this isn’t a city for bikes. Save your knees.

If you get sick
If anything goes sideways health-wise, cross over to Viña del Mar. Better clinics, more structure. Say you have insurance and move quick.

The people
The people? They make the place. Porteños will feed you, argue with you, guide you, and sometimes blow your mind with an unsolicited story. They’ll warn you. They’ll help you. They’ll talk your ear off. Valparaíso es su gente, and they wear their truth out loud.

A few unspoken rules
Don’t be too cool for a tour guide. Book a local one. Say hi to the dogs—they run the place. Don’t expect anything to start on time, and don’t be surprised when plans change mid-step. Always carry layers. Morning fog burns off by midday and then it’s sun until dinner.

Culture, ink, and chaos
Art lives inside places like Marginal Gallery, Espacio Rojo, and Bahía Utópica. And if you’re looking to take home some ink, check out @Relibs.
And then there’s the language. Even if you speak Spanish, Chilean Spanish might leave you blinking. A phrase like “that rooster is a duck and acts like a mussel, but should lower his ponytail” isn’t a riddle—it just means “he’s broke and has a bad attitude.”

Final thought
If you come to Chile and skip Valparaíso, you missed the soul of the country. You did the sanitized, postcard version. That’s fine—just promise yourself you’ll come back and do it right next time. Valparaíso is not clean. It’s not calm. It’s not easy. But it’s art on walls, fish on your plate, music down an alley, and history that hasn’t been whitewashed. It’s chaos with soul. And if it’s for you, you’ll know it the second you arrive.​