Wanderlust Wendy

City Guide: Wander in the Artsy Hills of Valparaiso, Chile

A Workaway experience that turned awry unexpectedly took us to Valparaiso for three weeks, where we worked on a different Workaway project. This hilly seaside town surprised and delighted me in the best way. Our three-week stay here allowed us so much time to expand beyond the usual tourist bubble, and see this unique city for all that it has to offer. 

When reading up on Valparaiso before arriving, I had an image of a sleepy beach town. Turns out, Valpo is a sprawling seaport. Thanks to the California Gold Rush, Valparaiso was once Latin America’s Largest port city. Today, Valpo relies heavily on tourism, especially after named as a UNESCO World Heritage site. The narrow alleys are filled with street art. Musicians filled street corners and restaurants.


Other than our Workaway stay, we ended up staying at three different places in Valpo, and they are each wonderful for various reasons. 

Cerro Alegre Guest House

We booked this hotel last minute and were delighted. The booking had a private room with a shared bathroom. The bedroom was very spacious and comfortable, the bathroom was modern and clean, and wasn’t at all annoying that it’s not en suite. The property had helpful reception staff. Decent breakfast. The room faced the street so it can get a tad noisy. Recommend this place if you are looking for a short stay. 

Airbnb Room

This place more akin to a boutique hotel than your typical AirBnB stay. An American/Chilean couple renovated an entire narrowed building into a beautiful light-filled space. The stay was cozy, comfortable, and quiet, hidden inside of a very unassuming entrance. The location is still right in the middle of the touristy neighborhood, with walking distance to many of the sights. 

Casa Verde Mackenna

This property was our final place in Valpo and our favorite. We took a private room in this hostel. Owned by a warm and hospitable elder couple, this hostel is in an old house and filled with charm. The rooms are spacious with a gorgeous high ceiling. The outdoor space has a beautiful view, and the space is very inducive to meeting people. We used the communal kitchen often since the location is further away from the main tourist thoroughfare. Recommend this space for longer-term space, or if you simply want something a bit more authentic.  

Things to Do

For the better part of our stay in Valpo, we were working with a Workaway project. In our free time, we explored the city by wandering around a lot without any particular purpose. Aimless wandering truly is the best way to see Valparaiso, and to observe lives within its various nooks and crannies.

Free Walking Tour

Many free walking tour providers take place in Valpo, and we went with Valp’Otop, a french-speaking tour group. The group size is much smaller than the typical free tours in English, which make for a less herding feel when walking the streets. We were very impressed by the depth of history and culture topics covered on our tour, and would highly recommend this group if you are a French speaker. The group meets at 3:30 pm daily at Plaza Sotomayer

Take the Funicular

Valpo reminds me of a mix of Hong Kong and San Francisco in many ways, with its busy port, steep hills, and beautiful colors. But mostly, the hills. Strolling the city absolutely gets the heart rate going. Fortunately, there are quite a few funiculars throughout the city that transport residents and tourists alike up and down the hills. We did notice the funiculars in the more touristy bits of the town are better maintained than the more local neighborhoods. Nevertheless, it’s a great way to avoid hiking up a hill, with a fantastic view to boot. Ascensor El Peral and Ascensor Reina Victoria are two notable funiculars in town. 

Hunt for Street Art

Valparaiso is plastered with incredible street art, even in less-touristy neighborhoods. Local artists also change them often. We saw quite a few live paintings in action. Hunting for these unique street art gives the flâneurs among us an extra incenter to aimlessly roam the city. We just never know what art we may chance upon. 

Spot Architecture Gems

While you hunt for street art, also keep an eye out at the variety of architecture in Valparaiso. Many of the houses are creatively positioned to accommodate the steep hill. Perhaps it looks like a small two-story on one side, but turn the corner and you’ll see it may actually span four stories! Like many seaside towns, often, buildings were historically covered in corrugated tin and painted in bright ship colors to prevent rust. Baburizza Palace, in particular, has an interesting history.

Enjoy the Local Parks at Dusk

For our time at the Workaway project, we were located in a less touristy neighborhood. At dusk, we often descend from the hilltop and enjoy local life by sitting at the park and see what people are up to. Sometimes, we treat ourselves to ice cream. Local parks always give me a sense of life in a place. Around the world, they are often similar, yet with hints of uniqueness, whether it’s the snacks served, or gamed played. We rotated between Plaza de la Victoria, Parque Italia, and Plaza O’Higgins

Have a Drink at Winebox Valparaiso

Our Workaway site was situated next to Winebox Valparaiso, a hip hotel made of shipping containers. We stopped by one evening for happy hour drinks on the rooftop. Great view of the city and very decent wine. Recommend to deviate from the touristy bubble and head this way for a different vibe of Valpo. 

Day Trips from Valparaiso

Vina del Mar

Valpo is a seaport town, and as a result, doesn’t have great beaches. But many excellent stretches of beautiful beaches are located just a short train or bus ride away. We took the train to Vina del Mar, dubbed, “Vinami,” supposedly due to its similarity to Miami. I certainly wouldn’t go that far, but high-rise condos were indeed abound. This popular beach spot is within two hours of Santiago, which makes for a leisurely getaway from city dwellers. We also visited over a weekend, and the crowd was too scary for us to descend. I absolutely recommend a weekday visit instead. 


I much preferred our day trip to Concón, also a day trip that we took via bus from Valpo. The weather was a bit overcast, and perhaps why it felt less touristy. We took a bus from Valpo toward Concón and descended to have lunch at Kibo Sushi, a casual place but with really delicious food! With a full belly, we walked toward the beach to Playa Las Conchitas, then followed Av. Borgono along the westward. 

Starting at Playa Las Conchitas, we walked toward Playa Con Con, then down south, and caught the bus back to Valpo at Costa Borgono. The walk lasted a bit over two kilometers, with minimal tourists and maximum natural beauty – a tranquil change of scenery from the relatively more bustling Valpo life. 

Tip: Google Maps did a stellar job letting us know which bus or train to take to get around. In general, I always recommend downloading an offline version of the map for your destination and surrounding areas. Save the places you’d like to see on the map, in case you stumble pass them on your wanders. 

Good Eats

Tre Peces 

Delightful family-run seafood restaurant that sources their seafood sustainably from local fishers. Excellent quality food with comfortable, homey décor. I recommend going right as the restaurant opens; otherwise, you risk needing to wait quite a while for a table. 

El Peral

At the top of the hill, near Ascensor El Peral exit, is this lovely restaurant serving up beautiful and delicious food. The set menu at 8,000 pesos per person comes with two courses. Request for a table on the terrace to enjoy the view. If you are lucky, they hire great live musicians to add to the ambiance. 

Café Entre Cerros

We went to this lovely café twice, once for brunch, and the other for dinner. Didn’t even realize they serve a dinner menu until we were in a desperate search for a place that opens for dinner on Sunday evening. Delicious food both for our brunch and dinner meals, with a side of incredibly friendly service. 


Authentic Italian-style pizza in a cozy setting. We enjoyed sitting out on the patio surrounded by walls made of corrugated tin material.

Delicias Express Empanadas

Empanadas are stable snack food across South America. This place takes this stable to the next level. The sizes are larger, with a variety of flavors. We stopped here for afternoon bites several times throughout our stay in Valparaiso. Never disappoints! 

Good Morning Valparaiso

If you are looking for the American-style pancake, eggs, bacon/sausage combo breakfast, this is your spot. No frills and down to earth. Hard to mess up breakfast food, and this one hits the spot when you have that craving. 

Los Chile’s Mexicano

Located just next to our Airbnb, we went here for a late-night dinner and were surprisingly pleased by the food. Very satisfying Tex-Mex dishes with generous portions at reasonable prices. Comes with free chips and guacamole, and 2,500 pesos happy hour until well into the night. A decent place to add variety to your meals. 

Casa Dumplings

The Chinese in me gets the craving for some Asian grub every now and again. I was intrigued by this place when we walked by it and saw that it had decent reviews. The dumplings resembled the Shanghainese soup dumplings. While not 100% authentic, pretty darn good and certainly fulfilled my Chinese food craving in this Chilean seaside town. 

Restaurant Capri

I wanted to try pastel do choclo, a sort of corn pie that is a Chilean specialty, and this place delivered. Very creamy and delicious. A local restaurant targeting tourists. Prices are a bit high, and service a tad slow, but overall a fine place to try a few special local dishes. 

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