São Paulo, Brazil’s biggest city, may the business-like older sibling to Rio’s tanned and tarty beachgoing heartthrob, but don’t let its imposing, skyscraper-jammed cityscape fool you. It’s not all work in this surprisingly stylish, sassy South American super-city. A burgeoning style mecca is...

São Paulo, Brazil’s biggest city, may the business-like older sibling to Rio’s tanned and tarty beachgoing heartthrob, but don’t let its imposing, skyscraper-jammed cityscape fool you. It’s not all work in this surprisingly stylish, sassy South American super-city. A burgeoning style mecca is growing that’s full of boutique hotels, swank restaurants, luxe lounges, artsy fun and truly friendly locals.

Yep, they still don’t get too many tourists here so chances are the attractive Paulistas will be rather happy to see you. And if you come for Gay Pride (the parade drew nearly 3 million participants last June, making it the world’s biggest) there’ll be no shortage of Brazilians along the Avenida Paulista as part of your welcome wagon.

Still, São Paulo can be overwhelming. Traffic can get downright snarly during rush hours (Local execs navigate the city by helipcopter. Really.) and you do have to be mindful of your personal belongings (don’t look too touristy) in dodgy areas. But more and more the city is full of great shopping in the leafy and hip Jardins ’hood (hit the Rue Oscar Freire with your credit card in hand), abuzz with a bustling spirit, and a showplace of contemporary and fun retro design (think 60s-70s urban chic). And after dark, you can mix it up at world-class uber-clubs or kitschy drag-fests.

And do be prepared. Even if São Paulo doesn’t boast the sexy, balmy beach breezes of Rio, there are still no shortage of those classically attractive Brazilians to charm you.

By John Polly