Exploring (Parts of) Chile in 5 Days

Within the group of 40 travelers that have accompanied me this year, I care deeply about all of them, but none more than those that can side trip like a boss. Which is exactly what I and three other women did through Chile, in five days. Exploring Valparaíso, Casablanca, and Santiago seemed daunting in such a short amount of time, however; it proved to be quite easily done.

Renting a car and having a willing driver is key for this type of adventure.  We landed in Santiago and rented a car from Enterprise for the straightforward 1.5-hour drive to Valparaíso.  Take note that there is also an Enterprise at the Santiago airport in Spain.  Not that any of us would have made that mistake and booked a car in an entirely different country…but y’know, something to keep in mind.


Arriving in Valparaíso that evening, we stayed at the lovely and well-situated Hotel Fauna for two nights, giving us a full day in town to explore.  I have found that the best way to delve into any new city is a walking tour, and what is better than a “free” walking tour?

Granted you should tip your tour guide at the end of these free walking tours, I have never once thought that the guide did not deserve that tip (aside from that one time in Berlin, but it was freezing and our tour guide had a thing for standing in torrential downpours).

We joined Tours 4 Tips and our guide Camillo on a delightful and educational walk around the port, through Plaza Sotomayor, and up into Cerro Alegre with a ride on El Peral funicular.

On our own, we rode the Artilleria Funicular up to the National Maritime Museum and took in the panoramic view from Paseo 21 de Mayo.

We finished our day in Valpo enjoying the view of the sunset from the restaurant at Hotel Fauna.


The next morning, we indulged in one more filling breakfast on the balcony of Hotel Fauna before departing for Casablanca.  The quick 35-minute drive to Casablanca was spent figuring out which vineyards in this Chilean wine heaven were actually open.  You may want to do a little research before your trip, as we found most to be closed, not offering tastings/tours, or generally quiet due to it being off-season (June).

Our first stop was Viñamar which was a bit sleepy, but their tasting proved to be no joke.  The four of us split two tastings, each of which included 3 extremely full glasses of their sparkling wines.  The explanation of each wine was a bit lackluster, but we managed to have a fair amount of fun on our own…as six full glasses of bubbles will do to anyone.

Our second stop was Veramonte, a beautiful winery with a nice lunch menu.  Again, we seemed to be the only people there but that did not stop us from partaking in a few wine selections, pasta, and burgers!  One caveat would be that we had a bit of trouble finding the parking and actual entrance to the building.  Nothing a few Spanglish sentences and off-roading couldn’t remedy though.


After lunch, we drove the rest of the way to Santiago and our AirBnB in the Lastarria neighborhood which proved to be the perfect location for our last two nights in Chile. As we arrived an hour or so before sunset we Ubered to Sky Costanera, the tallest building in Latin America to catch a fabulous view of Santiago and The Andes.

We woke up the next day to join another walking tour, this time with Free Tours Santiago. Meeting in Plaza de Armas we had a wonderful tour guide named Franco who shared historical details and in-depth background on architecture and culture throughout all three hours.  Ending on Pío Nono, a street lined with well-priced restaurants catering to university students, we shared one Chorillana and one Terremoto – more than enough for all four of us.  Fighting the impending food coma, we strolled east along Avenida Santa Maria, then back west to check out Mercado Central and its seafood stalls.

Before our 3 am flight (never booking that again) we went back to the Lastarria neighborhood for dinner at BocaNariz, which boasts an extensive Chilean wine menu of 400 bottles. A flight of three wines can be ordered with dinner as well, we obviously all opted for this choice. Post-dinner we meandered the streets filled with boutiques and bars before driving back to the airport and saying goodbye to our trusty rental car (thank god for automatic cars on those Valpo hills).

If we had more time we most definitely would have stayed longer and adventured through other regions of Chile.  La Serena and Easter Island will have to wait until next time, but I am so pleased that I got to see at least a portion of Chile.

Natasha Schwartz
Natasha Schwartz

After nine months of international travel and with three months left to go in South America, Natasha has found that sarcasm works in every language once hand gestures are put into play. Home base is Los Angeles but new adventures are where her heart lies.

Find her at @nablahblahz or travelingundertheinfluence.com

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