When most people think of São Paulo, they immediately conjure up the smog-horizoned, high-rise infested, megalopolis of 20 million for which the expression “concrete jungle” is an understatement. Teeming with noise, activity, and a certain degree of urban chaos, São Paulo is bewildering for those unfamiliar or unenamored with cities its size—and enchanting for those who are. Brazil’s economic and cultural powerhouse (having long supplanted Rio on both fronts) is overflowing with banks and mega corporations as well as an astounding number of world-class museums, cultural centers, theaters, concert halls, and cinemas.

Rife with contrasts and contradictions, São Paulo mingles First World sophistication with favelas. Haute couture and haute cuisine coexist alongside camelôs (illegal sidewalk vendors) hawking pirated Armani shades and makeshift vans selling deliciously messy hot dogs for R$1. While the working rich rely on the world’s largest fleet of private helicopters to commute from posh suburbs to glittery office buildings, the less fortunate—and far more numerous—working poor spend hours snarled in kilometrical traffic jams caused by the world’s largest fleet of municipal buses

If you’re looking for Brazil’s quintessential tropical paradise, you won’t find it here. However, you will encounter a unique and fascinating fusion of elements from all over the country—and the world.

The surrounding state of São Paulo is as diverse as its capital. The wealthiest and most populous of Brazil’s states—as well as the most developed in terms of industry and agriculture—São Paulo is also rich in impressive natural attractions. The coastline leading north from the historic city of Santos up to Rio de Janeiro is lined with stunning white-sand beaches backed by native Atlantic forest.

São Sebastião is a teeming hot spot with every kind of water sport imaginable and nonstop nightlife. Meanwhile, north of Ubatuba and on the island of Ilhabela you’ll find primitive beaches that you can have all to yourself.

Traveling inland offers similar contrasts: While the mountain resort of Campos do Jordão attracts a fur-clad crowd with a penchant for fondues and fireplaces, the tiny colonial towns and century-old coffee plantations of the Serra da Mantiqueira range remain largely unknown even by many native Paulistanos (natives of São Paulo).

Well-maintained highways and an extensive and efficient bus system mean that most attractions are easy to get to: All it takes is a 2–3-hour drive from the city and you’re in another world.

The Best of São Paulo

• Avenida Paulista
• Museu de Arte de São Paulo
• Parque do Ibirapuera
• Campos do Jordão
• Bananal
• Ilhabela