Your Supreme Itinerary: 4 Days in Santiago, Chile

Buckle up, fellow travelers, because this week you’re in for a treat. I just got back from a week in Chile with my lovely sister, and aside from some minor details (like freezing showers and cancelled flights), we had the most epic sister trip ever. We spent 4 days in Santiago, Chile and put together a pretty killer itinerary. You’re going to want to take notes 🙂

We’re doing it a little differently this week, and my sister (Amy) will be helping me write the post. She’s quite the comedian, so enjoy!

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Day 1 | Bike Tour of Santiago

(As written by my sarcastic sister Amy)

If you know my sister well, you should be aware that she has many wonderful qualities, but grace and coordination are definitely not two of them.  That being said, when I heard that we were going on a biking tour of Santiago, I feared that a South American emergency room visit was in our near future. Though biking probably doesn’t seem too dangerous to most, let me just tell you that I almost once lost Melissa. Read about the time she nearly biked right off the edge of a Hawaiian volcano. If that isn’t enough evidence to convey her recklessness, I can also vividly remember a time that we were merely pedaling along the very flat Florida streets when she somehow managed to tip off her bike and lose a chunk of her chin. I was definitely hoping that this experience with BellaBike would end differently.

4 days in Santiago, Chile; Santiago, Chile itinerary; what to do in Santiago, Chile; best day trips from Santiago, Chile

After arriving to the BellaBike headquarters and inquiring about training wheels for Melissa (they didn’t have any, FYI) they geared us up with the sturdiest possible helmets, introduced us to our guide, and sent us on our merry way. For three hours we pedaled around Santiago and learned about the history of the city and country as a whole. We even got to visit the local farmer’s market, which was by far the busiest farmer’s market I’ve ever attended! There we got a great taste of daily life.

4 days in Santiago, Chile; Santiago, Chile itinerary; what to do in Santiago, Chile; best day trips from Santiago, Chile

By the end of the tour I basically felt like a native and felt far better equipped to navigate the bustling city. I would definitely recommend that you go on this tour at the beginning of your time in Santiago, as the guide can show you museums, restaurants, and hidden gems that you must experience during your time there. And rest assured, if my sister can survive biking through the crowds and along the treacherous cobblestone streets, you can as well!

Day 2 | Cajon del Maipo

(This part is from me, Melissa!)

For day 2 of our 4 days in Santiago, Chile, we headed to Cajon del Maipo with BellaBike (again, yes…we really liked this tour company!) After packing into the van before the crack of dawn, we headed up toward the mountain, making scenic stops along the way.

4 days in Santiago, Chile; Santiago, Chile itinerary; what to do in Santiago, Chile; best day trips from Santiago, Chile

One of the first stops was an abandoned railroad track, and there were some cool ghost stories here…what are they, you ask? I’ll never know, because instead of sticking with our tour group, Amy bolted off running down the tunnel because it was cold outside that day. What’s an older sister to do but chase after her? At the end of the tunnel, she looks back for the rest of our tour group…but they’re nowhere to be found (obviously, duh, because they actually listened to the tour!) In the early fog of morning, she claimed that she didn’t know it was an actual tour through the mine, she thought it was a DIY kind of tour! Fortunately, we wisened up after that and stuck with the group the rest of the day to learn all the cool stories & history. So learn from our mistakes.

4 days in Santiago, Chile; Santiago, Chile itinerary; what to do in Santiago, Chile; best day trips from Santiago, Chile

After some additional picturesque stops, we made it to Cajon del Maipo, and it was absolutely breathtaking…the views were to die for. Here, we took some time to hike around on our own, have ridiculous photo shoots, and ended the day with a wine picnic with views overlooking the lake. For me, wine + pretty views = perfection. One important thing to note…there are no restrooms at Cajon del Maipo, but there is a very clean porta-potty you can pay to use…Amy and I both used it and lived to tell the tale, so you’ll be alright.

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Day 3 | Casablanca Wine Valley

(That’s right, back to Amy again here.)

Being a teacher of 8 year olds, a requirement of every vacation is finding an adult beverage hot spot. Luckily, in Chile there are many of these, as wine basically flows like water all throughout the country. Nearest to Santiago is the Casablanca region that, according to our brilliant HecTours tour guide, features 25 beautiful wineries. My sister and I could have stayed for 4 weeks in this region, but unfortunately only had half of one single day so we had to make the most of our time there. Luckily, our guide was able to pick out one of the best wineries in the region, the Emiliana Vineyard, and organize a tour and tasting for us.

4 days in Santiago, Chile; Santiago, Chile itinerary; what to do in Santiago, Chile; best day trips from Santiago, Chile

Upon arriving at the vineyard we learned that it was an organic vineyard fertilized by their very own adorable alpacas and chickens that produced not so adorable “black gold” aka droppings. We also learned that this was a biodynamic vineyard (didn’t even know that was even a real word), which is apparently a method of planting involving astronomical configurations.

4 days in Santiago, Chile; Santiago, Chile itinerary; what to do in Santiago, Chile; best day trips from Santiago, Chile

After becoming wine experts, expanding our vocabulary, and attempting to get selfies with a few alpacas, we finally got to my favorite part—the tasting. As if our guide knew that our wine would taste better in a small group setting away from the main tour, he kindly arranged a separate tasting just for us! Let me tell you—the wine did NOT disappoint. A few glasses of wine and a slight buzz later, my sister and I were headed with four newly purchased wine bottles in tow to the next stop on our journey.

Day 4 | Viña del Mar & Valparaiso

(And throwing it back to Melissa for the finale.)

On your last day in Santiago, head on over to Viña del Mar & Valparaiso with HecTour Services. Viña del Mar is more of a resort town, and is great for a quick stop and lunch overlooking the ocean. Make sure to check out the flower clock and moai statue while you’re in town.

Then drum roll for Valparaiso…one of the most colorful cities I’ve ever visited! And everyone knows when two sisters travel to a colorful place with awesome street art, you can’t help but have insanely fun photo shoots throughout the city. Hector (our guide) knew all the top murals around town, so we cruised up and down the hills, exploring Alegre, Bellavista, and Concepcion, to name a few. I actually wrote a whole post on the best places to take photos in Valparaiso because we loved it and had approximately 2 million pictures from the day. For now, I’ll leave you with a few of my fave pictures around the city…you’ll have to check out the Valpo post for my top 20!

4 days in Santiago, Chile; Santiago, Chile itinerary; what to do in Santiago, Chile; best day trips from Santiago, Chile

4 days in Santiago, Chile; Santiago, Chile itinerary; what to do in Santiago, Chile; best day trips from Santiago, Chile

If You Have Extra Time…

If you have spare time in Santiago, I have plenty of suggestions on what to do to fill your days.

  • Mountain Horseback Riding – Gallop through the rugged mountains of Chile while experiencing views like no other.
  • Santiago Food & Walking Tour – One of my favorite things to do in a city is to do a walking food tour. Not only do you get a taste for the local cuisine, but walking helps make sure you still fit in your pants at the end!
  • Santiago hop-on, hop-off bus – If you’re not in the mood to walk or bike the city, the hop-on, hop-off bus tour is an easy way to see a lot in a short period of time.
  • Portillo Inca Lagoon – Last but certainly not least, is a day trip to a beautiful lagoon in the Andes Mountains. Best of all, this tour includes a stop at the San Esteban vineyard…and everyone knows wine only improves the experience!

Logistics

Cheap Flights to Santiago: I’d recommend checking out Momondo. They scan tons of different travel discount sites and let you filter by cheapest, best, and shortest. You can typically find good flights into Santiago; I’d suggest avoiding LATAM if at all possible. We flew them down, and while it was cheap, it was an absolute nightmare, and ended up being a 54 hour journey door to door…save yourself the misery and fly literally any other airline. Also, check out booking a private transfer to your accommodation in advance…navigating the metro looked impossible to my sleep-deprived self, and the taxi stand wasn’t much better.

Where to Stay in Santiago: Santiago has a little bit of everything, from quirky hostels to luxurious hotels and everything in between. For the backpacker option (and my own personal hostel choice), check out La Chimba Hostel in the Bellavista District.  The Bellavista district is super artsy and colorful. Plus the hostel is located a street away from one of the main party scenes in the city; it’s also cool just chilling in the hostel courtyard with a bottle of wine (the pic below is the hostel!) For the hotel route, I’d recommend Hotel Solace Santiago.  The hotel has a great location in the Providencia neighborhood, and includes a sun terrace with views of the city! If you’re traveling with friends, another good option here is to do an Airbnb. (Use my link for savings on your first stay!)

4 days in Santiago, Chile; Santiago, Chile itinerary; what to do in Santiago, Chile; best day trips from Santiago, Chile

Additional Chile Resources: For more awesome resources on Chile, make sure to check out the top 20 Instagrammable places around Valparaiso.

And there you have it, an epic 4 days in Santiago, Chile, and the most fun-filled itinerary you could ever wish for! So have you been to Santiago? Hit me with your fave things to do in the comments!

P.S. This post contains affiliate links. If you click one and make a purchase, I might make a little extra spending money, at no extra cost. As always, all opinions are my own. 

4 days in Santiago, Chile; Santiago, Chile itinerary; what to do in Santiago, Chile; best day trips from Santiago, Chile

4 days in Santiago, Chile; Santiago, Chile itinerary; what to do in Santiago, Chile; best day trips from Santiago, Chile

4 days in Santiago, Chile; Santiago, Chile itinerary; what to do in Santiago, Chile; best day trips from Santiago, Chile

6 thoughts on “Your Supreme Itinerary: 4 Days in Santiago, Chile

  1. My mom and Amy would get along! She text me a picture in high school of a bloody towel over her nose (which was broken) after she flipped her mountain bike on a crazy trail. I am definitely more cautious! Santiago looks so beautiful, the views and the alpacas are the best 🙂 I can’t wait to adventure there one day!

  2. What a colorful place! So lively and fun. You and your sister remind me of when I’ve traveled with my daughter and had so many good times — girl trip! We’ve been to Europe, San Francisco, Disney World. When you have a great traveling companion, the trip is extra fun!

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