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The capital city of Chile is a beautiful place to spend a few days immersing yourself in the Chilean culture. Most of the city is more modern, clean, and the locals are friendly. That being said, this city is more of a city that you experience rather than being filled with a ton of places or sites to see, so you could easily explore what you need to in about 2 days.
The two major sites that you should see while visiting, is Plaza de Armas and Santa Lucia Hill. Plaza de Armas is the main square in Santiago and it is here that you will be able to see beautiful architecture, including the Cathedral of Santiago, street performers, shopping, and local food carts. Tourists and locals alike gather here throughout the day to take in the energy of the square and partake in any festivities. As mentioned above though, this is a prime spot for pick pockets and is not the safest area to be after dark, so if you plan on visiting, do so in the day, and stick to the square rather than wandering down too many of the side streets. There is a metro station right at the corner of the square so you can hop off, check it out, and then hop back on without straying too far. Santa Lucia Hill, on the other hand, is a beautiful place to spend an evening and catch the sunset. You can take the somewhat easy trail to the top of Castilla Hidalgo to take in a panoramic view of the city or get the perfect photo op in front of the Fuente de Neptuno.
The best way to explore Santiago is to visit the different neighborhoods throughout the city, each offering something unique to be explored. The three best to check out are Lastarria, Barrio Bellavista and Vitacura. Bellavista is the artsy neighborhood of the city, where you will find colorful buildings, lively bars and restaurants and being the backpacker part of the city, plenty of budget accommodations. While this is a fun area to check out, we were warned by locals that it does experience more crime than in other parts of the city and is not the safest place to be at night, so if you just want to see the area, head there during the day and enjoy lunch, rather than partaking in the club style nightlife. Vitacura is the more modern neighborhood in the city. It is slightly on the outskirts of town, but here you will find plenty more upscale bars and restaurants. Stroll along Alonso de Cordova and Avenida Vitacura to take your pick of eateries. The best neighborhood to spend your time in though is Lastarria. Here you will find European style streets with boutique shops and restaurants, with many of the places we recommend you to try being located here. Take your time exploring the streets, popping in to a local wine bar, discovering piscos, and doing a little shopping.
If you are looking for a day trip from Santiago, we would recommend heading over to Valparaiso for the afternoon for a little change in scenery. When planning our Chilean itinerary, we debated if we wanted to spend a night or two here or if we just wanted to do a day trip, and we are very thankful that we just did a day trip. While it was something different to do, the city itself is not considered safe and therefore you have to stay confined to one section of the city and there is not a lot to see or do there, and can be explored in a few short hours.
If you do choose to go there, we will reiterate that this city is known to have high crime rates with minimal security presence in many parts of the city. The tourist area of Cerro Concepcion is safe and this is where you will be spending your time if you visit, but when you arrive in town, most likely via bus, do not linger in the bus station, do not flash valuables, and do not try to walk from the station to another area of the city as the surrounding neighborhood is dangerous. Get to the taxi bay and go straight to Cerro Concepcion, this is what we did and we did not have any issues during our day trip there.
Getting to Valparaiso is relatively easy, the bus leaves from Terminal Pajaritos about every 20 minutes and costs about $12 round trip. We recommend purchasing your ticket at the station as there are a few different bus companies that run the route and they will put you on the best price or next time options. The buses often have 1st and 2nd class seats but a great tip is to ask the ticket office attendant if they have the front seats in 2nd class available as these will be in the front on the upper level and offer great views through the large window. These are also the only seats in 2nd class that recline fully.
Once you reach Valparaiso and get to Cerro Concepcion, take your time exploring the streets, checking out the local shops and restaurants. Grab yourself a coffee or do a local wine flight and enjoy views out over the ocean.
Another excellent option for a day trip from Santiago is visiting the nearby Maipo Valley, because it would be a shame not to get out and explore the Chilean wine country when you are that close! You can get there by Uber which takes about 30 minutes and costs around $40 each way.
There are a few different wineries in the area that you can visit (be sure to call ahead and make sure they can accommodate your party), but our favorite and a must visit is TerraMater. This family owned winery offers a wide selection of local varieties and you can reserve a private tasting for $20 per person, which includes not only wines but also a tasting of their olive oil! Once you have enjoyed your tasting, you can head over to their on-site restaurant Zinfandel for a wonderful lunch and possibly another glass, or dare we say bottle, of wine!
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