The chaos, vicious traffic, and poor urban planning of São Paulo, a giant sprawl of 18 million people and 4 million cars, can be pretty daunting. This never-sleeping city is all about making and spending money, and lacks the exotic tropical beauty of Rio, but it is the financial, gastronomic, and cultural center of Brazil. World-class restaurants, a strong work ethic, vibrant nightlife, and friendly people make this metropolis more interesting than it seems at first glance.

Street renovations, tree planting, a recent ban on advertising billboards, and a project to revive the old center have spruced up São Paulo. That said, the poverty and crime coexisting with the wealth can make drifting off the beaten path unpleasant and risky. For a growing number of well-heeled Paulistanos, the answer to traffic and violence is helicopters (the city boasts one of the world’s largest chopper fleets), and many business people use armored cars and private-security services.

Where to Sleep
Stay in the posh Jardins district, where it’s fairly safe to stroll and you’ll be close to the best restaurants, cafés, and luxury shops, as well as to the main business areas. Follow supermodel Gisele Bündchen’s lead and book a room at Emiliano, a luxe designer hotel in the heart of Jardins that has a butler-per-room policy. At the stylish Hotel Unique, the hip rooftop bar has a swimming pool with a glass floor (that lets light through to the atrium underneath) and views of Jardins’ and Ibirapuera’s treetops and Avenida Paulista’s skyline. Hotel Fasano opened in 2003 but, with its Art Deco lines and Italian flair, feels like a classic that’s been around for decades. Its namesake restaurant is one of the city’s classiest, and the chic jazz bar off the lobby is a world-class destination for music lovers. Brazilian singer and composer Caetano Veloso felt so at home here that he rented out a suite for two years. The Renaissance, also in Jardins, may be more conventional, but it pulls in heavy hitters such as former president Bill Clinton with living-large details like the Havana Club bar, which offers appetizers and cocktails to complement its lineup of cigars.

Where to Eat
At D.O.M., chef Alex Atala uses the best Brazilian ingredients and classic French techniques to whip up dishes such as pork loin with Santarém beans and Amazon salt for his pampered diners. Look for billionaire industrialist Antonio Ermirio de Moraes and supermarket tycoon Abilio Diniz among the celebrities, politicians, and CEOs tearing into the Brazilian and Argentine grass-fed, free-grazing beef at Churrascaria Rodeo steak house. The menu at Figueira Rubaiyat, a casual glass-ceilinged restaurant built around a giant 130-year-old fig tree, combines seafood with Brazilian steaks and feijoada, a rich stew of black beans and pork.

Where to See and Be Seen
Spot, a small glass-walled restaurant and bar amid the skyscrapers of Avenida Paulista, has buzzed for a decade with a fashionable crowd of media insiders and artists (designer brothers Fernando and Humberto Campana, to name two). Kosushi is the sushi bar of choice of João Paulo Diniz, the socialite son of Brazilian supermarket billionaire Abilio Diniz, and other heirs and young business leaders. Afterward, they hit the dancefloor at Lotus, a branch of the New York nightclub that offers a heliport to jet-set clubbers like Naomi Campbell.
 
Where to Close a Deal
The glass walls overlooking a private garden create a reserved yet luminous ambience at O Leopolldo Plaza, a power lunch favorite for industry leaders such as sugar and ethanol billionaire Rubens Ometto. Shintori serves Japanese food to Avenida Paulista execs from Citigroup and the São Paulo state industry association (FIESP), Brazil’s leading business conglomerate. The glamour of the Terraço Italia restaurant/piano bar has faded somewhat since the 1970s, but its unrivaled view still attracts brokers from the commodities and futures exchange, Latin America’s biggest market.

Local Codes
Brazilians are informal and like to create a rapport through jokes and chatter. Collegial backslapping and hugging are part of the manly manners of the older generation. Among the young rich and powerful, for whom an MBA from a renowned business school is a must, the code is not all that different from New York’s: Business hours generally go from 8:30 A.M. to 6 P.M., but São Paulo workaholics often stay in the office until 7 or 8 P.M.

Airport Intelligence
São Paulo-Guarulhos International Airport (also known as Cumbica, after the neighborhood it occupies) is only a half-hour drive away from central São Paulo on a Sunday afternoon, but the trip can take four times as long during rush hour. Expect long lines for luggage check-in and immigration. Delays have become more routine following two Brazilian plane crashes in ten months, which has contributed to tensions between air traffic controllers and the government. To avoid these problems, some business people use private jets.

The Three-Hour Tour
Stroll along Oscar Freire and Alameda Lorena, the two main shopping streets of Jardins, stopping in the cafés Santo Grão and Café Suplicy for a taste of Brazil’s best coffee. Wander, too, into trendy shops; worth a stop are designer Alexandre Herchcovitch’s namesake fashion temple and the Clube Chocolate store. Walk to MASP—the museum of art, in the middle of Avenida Paulista—which displays works by Rembrandt, Hieronymus Bosch, Van Gogh, Chagall, and Toulouse-Lautrec (bought from European families after World War II by Brazil’s late media tycoon Assis Chateaubriand). For a glimpse of Gothic-style Sé Cathedral, the São Bento Monastery, and other downtown landmarks, Odyssey South America offers guided walking tours that may include a trip to the viewing platform atop the Banespa Tower (mornings and afternoons, Mon.–Sat.).

–Eduardo Hansen