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Valparaiso Street Art & Casablanca Wine Day Trip from Santiago

★★★★★★★★★★ 4.88 (144 reviews) 94% rated it 5 stars

Free cancellationTravelers' pick

1/23

Duration9h

GroupUp to 8

LanguagesEN · PT +1

PickupAt your hotel

Valparaiso’s painted hills, port life, and a Casablanca wine break

You’ll walk downhill through Valparaiso’s wild street art hills with a small group, ride an antique funicular, feel the sea breeze by the fish market, and end your day sipping wine among Casablanca Valley vineyards. Expect real local flavors, unhurried wandering, and moments that linger longer than you’d expect.

Step-by-step itinerary

Visit Pacific beach and fish market
Explore Cerro Bellavista and Pablo Neruda's house
Enjoy panoramic views at Bismark Square
Walk downhill through Cerro Alegre
Tour historic streets of Cerro Concepción
Ride Concepción Funicular elevator
Take boat cruise along Valparaiso bay
Wine tasting at Casablanca Valley winery

The Experience

“You see that mural?” our guide asked, pointing at a riot of color stretching up the side of a crumbling house in Cerro Alegre. I was still chewing on a pastry I grabbed from a tiny bakery—couldn’t resist the smell—and almost missed his story about the artist sneaking out at 3am to finish it. The whole morning felt like that: surprises tucked into every corner. We’d started at the beach near the fish market, where pelicans strutted around like they owned the place and old men argued over who had the freshest reineta. The salt air stuck to my skin in a way you don’t get in Santiago.

Walking downhill through Valparaiso’s hills is kind of like leafing through someone’s sketchbook—some bits wild and messy, others so detailed you have to stop and stare. Our group was small (thank god), so we could actually hear each other and wander off for coffee or just to take photos without feeling rushed. At one point, Li (our guide) laughed when I tried to pronounce “Ascensor Concepción”—I probably butchered it, but she was nice about it. Taking that old funicular down felt like stepping into another era; the wood creaked under our feet and for a second I wondered if it would make it all the way.

The boat ride along Valparaiso’s bay wasn’t even on my original must-do list, but watching those painted houses stack up against the blue sky from the water—I still think about that view sometimes. There was this weird quiet out there too, just wind and gulls, nothing else. Afterward we had free time around Bismark Square (I found empanadas with way too much cheese—no regrets), then headed back toward Santiago with a stop in Casablanca Valley. The vineyard air smelled sweet and green; I’m not really a wine person but something about sipping chardonnay while looking at rows of vines just makes sense here.

I left with paint smudges on my shoes and sand in my bag—not sure how long those will stick around, but I kind of hope they do.

What’s included

Your day includes private transportation from Santiago with pickup, all entry fees including the historic Concepción funicular ride in Valparaiso, guided walking through multiple painted hillsides strictly downhill, free time for your own lunch choices or exploring hidden cafes, an atmospheric boat ride along Valparaiso’s bay (weather permitting), plus a signature wine tasting at a Casablanca Valley winery before heading back in the evening.

Good to know

Easy physical levelWheelchair accessibleAccessible transportStroller friendlyInfant seats availablePets welcomePublic transport nearby

Operated by Progressive Tours