Looking for recommendations for things to do in Santiago, buenos aries, Montevideo, São Paulo and Rio de Janeiro!

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I am a Brazilian so I can only speak on the brazilian cities. In Rio go to Ipanema beach, a lot of of the tourists stay in Copacabana but Ipanema is the carioca gem. Definitely go to Lapa, it's a neighborhood full of bars and samba, choose one with live music and happy hour. Do not take cabs in Rio, they are all scams, only take Ubers. If you have time, go to Buzios, Angra or Ilha Grande , they are cities near Rio and they are so beautiful. If you drive from Rio to Sao Paulo, Paraty is a must go city, Brazil started in Paraty, so it is a very rich city. In Sao Paulo you need to go to Avenida Augusta (it has all of the famous bars and fun clubs in the city). Avenida Paulista, is the most famous street in south america, walking there is super special for anyone, specially on Sundays when they close the street. Bairro da Liberdade in Sao Paulo is one of the biggest japanese community in the world (Brazil has the largest community outside of japan) and bairro do bexiga is the same for italians, you must eat our pizza (portuguesa is my favourite). You must also go to Mercado municipal eat a pastel de bacalhau or a pao com mortadela, you will love it. Saturday is feijoada day, going to brazil and not eating feijoada is like getting married and not having sex, so do it!. Brazil has some of the most famous grafitti artists in the world, in Rio go to mural etnia, in SP go to beco do batman, they will take you breath away. Make friends there! Although Brazil is super dangerous is also super friendly, we love people in general so if you make friends, you will be treated well and will always have a place to come back.

Thanks for the recommendations!When you say super dangerous, what should I be careful of?

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I do not recommend you to use your phone on the streets, bags should be always zipped, locked and very safe with you. There are three main types of crimes in Brazil: pick pockets, thieves that pass running and take all of your things and gun point robbery. I would avoid going out by yourself in the evenings, in SP cabs are super safe, but uber is always an option and always be aware of your surrounds. I know! It is terrible.

We went on a tour package to the Santa Susana Gaucho Ranch from Buenos Aires. A bit touristy but fun none the less. All day minibus trip with English/Spanish guide. A few years ago we did an all day wine tour to the Casablanca Valley from Santiago, which was also quite nice.

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