The first time I went to Santiago was in June 2010. As I don't remember all the details of the 4 days I spent there, I'll give you a summary:
I stayed in a great hostel, Aji Hostel, which is very close to the Salvador subway station. The hostel is located in the neighborhood of Providence, which for me is one of the best neighborhoods in the city along with Bellavista. It is an extremely residential neighborhood, with little hustle and bustle, but it is very safe and clean. The room I got was a suite and was very pleasant. The breakfast was very simple and tasty and the events that took place in the common area of the hostel were very lively.
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The only nice restaurant I visited this time was Revolving Restaurant, which, as the name suggests, rotates and has a really cool view of the city. The cool thing is that a full meal is enough time to see the city from all angles. The food was delicious, especially the breads (I remember they surprised me). Detail: I went in the late afternoon, so I saw the city during the day and at night… I recommend it!
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I only visited the winery Shell and Bull, which I thought was wonderful, but I intend to go back to see the others. I went on my own, without hiring the excursions that people normally hire for more than US$$50. I took the subway from the station Savior and got off at the station The Mercedes (blue line). Then I took metrobus 73 (but you can also take 71, 83 or 84), which dropped me off at the winery in less than 20 minutes. The whole trip took over an hour and was very cheap (if it cost R$$10 it was a lot). If you want to do it on your own, plan to arrive before the last guided tour. Oh, and it's important! You have to make a reservation with them before you go. They offer several types of guided tours with different prices and if I'm not mistaken, I did the traditional one. I tasted some wines and was even lucky enough to see the sunset there. Excellent!
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I booked a full-day tour at the hostel to Valle Nevado and surroundings. I thought the tour was great because they picked me up at the hostel, gave me snow gear, drove me along a very winding road, offered me a delicious lunch in a cute little town, stopped at beautiful places for photos and on the way back, dropped me off at the mall Arauco Park. I don't remember how much it cost, but I remember thinking I would do it again. When we stopped in Valle Nevado, the resort The ski resort was still closed, but we were able to play in the snow and enjoy the view. Look how beautiful:
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In Santiago, I just walked around the neighborhoods of Providence and Bellavista. I loved both, especially Bellavista, for having a more bohemian and youthful side. I went up the San Cristobal Hill, which has a spectacular view of the city. To go up and down, I used the funicular, which is a kind of tram. At the top of Cerro, there is an image of Virgem Maria and halfway, it is possible to visit the city zoo.
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That's all I remember from this trip. 🙂