Chile is the perfect place to get a taste of it all! You can take the subway to a museum, go skiing, tour a vineyard, walk on the beach, or wander the coastal towns. Spend at least five nights to get the variety of experiences.
Santiago:
The Basics
We flew into Santiago from Medellín via Avianca airlines. Their international airport seems to serve quite a few cities around the world, making flights possible from all over.
On our way out the airport, we were greeted by taxi drivers shouting at us. We ended up grabbing a certified taxi and confirming the fare with him before getting in. Taxis in Santiago are metered but additional fares may apply such as using highways. If you’re not in a rush and you’d rather save a few dollars, you might ask if there is another route the driver can take. Cost from the airport to downtown was $19,000, but the way back cost only $14,000.
Getting around the city is possible by bus, metro (micro), or taxi. Uber is available, but not currently legal. I thought the metro was easy to navigate with plenty of signage and color-coded routes. Cost for a one-way fare ranges by the hour (high traffic means higher rate), but is about 600-800 cents (about $1).
We chose to stay next to Santa Lucía Hill a few blocks from the central plaza. I recommend Altura Suites if you like having your own kitchen and a place that feels more like home. Also, the bed was unbelievably comfy!
Get Your Adventure On
Centro Cultural Gabriela Mistral: This visual arts museum has free entry with some permanent and rotating exhibits. We saw a small display of arpilleras, woven fabric scenes. I liked walking around and noticing the ongoing events: dance groups gathered to practice, local bands playing a concert, and artisan craft booths set up.
Spicy Chile walking tour: This tour is technically free but expect to pay a donation. It is a comprehensive 3-hour tour around the city. For me it was a great way to see the highlights and get some interesting historical and cultural info along the way.

On New York street in Santiago, named for being the financial district
Bellavista neighborhood: This area is a combination of outdoor shopping malls, restaurants, and the kind of clubs that beg you in with free drink cards. It wasn’t necessarily our style but worth a walk around. During the daytime would be nice to see the colorful graffiti art.
Museo de la Memoria: Although it’s hard to stomach, this museum is worth the visit to learn the history and honor the victims of this tumultuous time in Chile. It is easy to access via metro on the 5 line exiting at Quinta Normal.
Museums: Want to experience the culture of the city for free? Many of Santiago’s museums are free to the public, or offer a free day. We visited Bellas Artes and Memoria, but would have seen others with more time.
Eats & Drinks
Colmado Coffee & Bar:Here coffee is done right. For the evenings, they also serve craft beers and local wine.
Bocanariz: We loved their creative menu with a robust wine collection, all from Chile’s vineyards. Truffle mushroom risotto was my personal favorite. On the weekends, this street is filled with local vendors and some street performance. Make a reservation!
Gluten-Free Empanadas: Near the intersection of Avenida Merced and José Victorino Lastarria is a row of shops and quick-stop eats, all popular with the hipster crowd of the city. At the end of it, we found this sweet man (with celiac) who runs a shop selling gluten-free pizzas, empanadas, and other celiac-friendly items. I was more than surprised to get to try a local-style empanada with hard boiled egg, olives, beef, and raisins.
What Next?
We didn’t get a chance to explore the mountains near Santiago. We would climb peaks and do a long trek for sure! If it was winter, we would get on the slopes. Okay, false. Jonathan would snowboard and I would drink hot chocolate.
Valparaiso:
The Basics
It was easy to grab a local bus from Santiago. The trip takes around an hour and a half. A few companies offer rides from stations in town. We took the metro red line to Pajaritos stop and got bus tickets upon arrival. The next bus was leaving in 15 minutes so we had a chance to grab a coffee and then board.
Get Your Adventure On
Tours 4 Tips: This tour was a favorite for me. In 2.5 hours, we got to see main highlights and back corners of Cerro Alegre and Cerro Concepción. Our guide gave great information about the history, culture, and street art. Again, this tour runs on tips.
Casablanca Valley: You can take your pick here: There are plenty of vineyards to taste and tour. All are a simple stop between Valpo and Santiago We luckily stumbled upon Kingston Vineyard which had a beautiful tour with a cheese and chocolate pairing, as well as an outdoor lunch dining experience. As a family owned boutique vineyard, I consider this an exceptional experience. To get there from Valpo, take a taxi colectivo on Avenida Argentina. The cost should be $1,500 per person to Casablanca’s town center. From the town center, take a taxi to your vineyard of choice (Kingston = $4,000 total).
Eats & Drinks
La Concepción: This spot was recommended by several locals, and did not disappoint. We got the curry shrimp, obviously with a bottle of wine.
Il Paparazzo: Another winning restaurant tucked inside the windy streets. Great wine selection and a variety of seafood dishes.
Emiliana Vineyard wine: You might ask around for wine from this organic vineyard in Casablanca valley. It was our favorite white blend!
What Next?
We only had one night in Valparaíso…not enough!! I could spend days wandering around these beautifully painted streets. During summer, I’ve heard that Viña del Mar, just north, has beach resorts. Yes, please!