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Santiago/Valparaiso/Wine Region - January 2018

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Hi, my husband and I will be in the Santiago/Valparaiso region for 4 days and 5 nights in January 2018 after spending 1 night in San Pedro de Atacama and 4 nights in Torres del Paine. We want to spend at least 2-3 full days in Valparaiso and a day visiting one of the famous wine regions in the area. Not sure whether we want to spend a full day in Santiago or just the last night before we fly back home.
20 Jan - arrive in Santiago at 9.25 pm and stay overnight
21-24 Jan - Valpariaso/Wine Region
25 Jan - Fly back from Santiago to Singapore - flight departing at 12.30 pm

1. Which wine region should we visit - Casablanca or Maipo?
2. Thinking we can take the bus from Santiago to Valparaiso on 20th morning and stay there for 2-3 nights and then visit Casablanca or Maipo on the way back to Santiago on the 23rd or 24th while stopping by a few different vineyards. Does this make sense? Should we rent a car for this trip? Or would a different order of itinerary make more sense?
3. Do we need to book wine tours in advance? What's the best way to do this on a budget while still enjoying a few different spots? Is it recommended to spend a night in the wine region?
4. Is there a lot to see/do in Santiago? We are less into touristy landmarks and more into absorbing the vibe of the city. We would have also spent an evening in Santiago on 15th Jan. Need to decide if we should return to Santiago on 23rd evening or 24th evening.

Any help on planning this part of our trip will be hugely appreciated! Thanks a ton.

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