Sao Paulo is a busy city and a great metropolis of more than 40 million people. It's the business capital of Brazil and not exactly an ideal destination for having fun. But like many metropolis, Sao Paulo offers excellent restaurants, a very animated nightlife and many entertainment options.
For Sao Paulo inhabitants, restaurants and the animated nightlife are the substitute of the beach life.
Bixiga, Jardins, Vila Madalena, Pinheiros
Nightlife in Sao Paulo, as in most Brazilian cities, begins at midnight. Bixiga's (also called Bela Vista or Little Italy, reflecting its original Italian population), adjoining downtown is an excellent zone for fun and music, with lots of restaurants, clubs, bars and night clubs and discos.
But there are other more well known locations, like Jardins, that aren't far from downtown and are much more secure. Jardins includes many X-rated and gay bars (though the bars tend to be mixed, without the homo-heterosexual division). The strip bars and alike are found, mainly, near Hilton Hotel or Caesar Park Hotel, on Rua Augusta and Nestor Pestana streets, at an area called Jardim Paulista.
Other good locations for nightlife options are Vila Madalena and Pinheiros (Pinheiros is adjacent to Jardins and Vila Madalena).
For a very selective club and bar options, Faria de Lima Avenue (also in Jardins area) is the best. Faria de Lima is one of the wealthiest zones of Sao Paulo, with several members-only clubs.
Sao Paulo is undoubtedly the biggest shopping zone in South America. For clothes and fashion, you can visit Rua Augusta, at the Jardins area. Also in this area, you can visit two very big malls, with an exceptionally wide set of offers: Shopping Eldorado, and Shopping Iguatemi.
Not very far from these shoppings, farther south, there are two other super malls: Shopping Morumbi (at United Nations Avenue) and shopping Ibirapuera (adjacent to the most famous park and sport zone of Sao Paulo: the Ibirapuera Park).
There is a cuisine and a restaurant for every taste, in Sao Paulo: Italian, French, Greek, Portuguese, German, Hungarian, Japanese, Arabian and so on. Paulistas like to bet on the variety and quality of other national cuisines as much as on Brazilian dishes.
Feijoada (black beans simmered with a wide variety of meets), peixe brasileiro (fish stew served with a dough based on manioc root) and churrasco (grilled meat) are very popular dishes. Also popular are Tutu Mineira (mashed beans with roasted pork, cabbage and rice), Acaraje (fried shrimp pie) or Virada Paulista (meat with rice, beans and banana). Bixiga district has thousands of restaurants. The downtown and other areas such as Jardins, Pinheiros, or the Ibirapuera Park, also have a great number of restaurants. But be aware: while there are some excellent restaurants, most of them have an average or even poor quality. As such, it's better to ask for local advice (at your hotel, for instance).