
Imagine New York. Now, imagine New York being twice its size, and having nearly 12 million people in it. And that's just the city -- with the suburbs, Sao Paulo jumps to nearly twenty million. Now, imagine inadequate public transport, a monstrous traffic problem and some major issues with crime. It immediately becomes clear why Sao Paulo, which owes its early growth to Brazil's booming coffee trade, isn't exactly a hotspot for the leisure traveler.
Get one thing straight, though -- this is no hardship post. Those who do come find Sao Paulo unforgettable. Sophisticated, rich in culture and diversity, nuts about eating and passionate about fashion and design, this city can seriously get under your skin. Love it or hate it, you won't soon forget it.
-- Carlos Rubin

This is a city that likes to run away from itself, evidenced by the obvious path trodden by the business community from the scruffy but vibrant Centro out to the towers of grey, soulless Avenida Paulista, and further on towards the glittering glass (and equally souless) canyons springing up along the Pinheiros River, even further west. Each move leaves a glut of office space in its wake, as businesses seek cleaner, better-lit and more secure environs in which to do business.
But this doesn't mean the center of Sao Paulo is empty -- not by a long shot. And no matter where the business community chooses to go, Downtown will no doubt always be the most appealing neighborhood architecturally, with plenty of commercial and residential buildings that echo New York in the 1920s. Enlist a guide to lead you through the maze -- start on the Praca de Se, where you'll find the city's main cathedral (completed in the 1950s), then head past the Patio de Colegio, where you'll see the restored Jesuit mission, built on the site of Sao Paulo's founding in the 1550s. Next, head across the bustling Viaduto do Cha, which runs above the sprawling Praca Ramos de Azevedo (itself covering up an expressway tunneling through the heart of town) and up to the Theatro Municipal, inspired by the Paris Opera, and completed in 1911. If there's something on while you're here, get tickets -- this Beaux Arts gem begs to be seen up close and personal.
While there's plenty of interest throughout the center proper, the Luz district is perhaps a better bet for hitting some of the city's most intriguing sites in a short time period. If you're near a station, hop the metro to Luz station, which will call to mind London's old rail terminals from the inside, and have you doing double-takes once you step out and see the restored facade (this Victorian gem dates back to 1901). Just across the adjacent Luz Park is is the memorable Pinacoteca do Estado, or the state art museum -- it's not expansive, but the restoration of the building, an old school, is as impressive as the art itself (the collection is modern). From here, you can delve into the lively schmatte district along neighboring Rua Jose Paulino, or, head past the station and down to the bustling Mercado Municipal (open 7 days), which is still a major hub for food distribution in Sao Paulo. This is a good place to sample Brazil's famous pao de queijo, or cheese puffs -- not to mention plenty more local specialties.
The green, low-rise appeal of the Jardins is immense, particularly after a few days in town. This district directly south of Avenida Paulista is a peaceful, exclusive respite from vertical malaise. But the Jardins -- actually a collection of neighborhoods with the Jardin label, almost impossible to tell apart, not that it matters -- is no suburb. It was and still is the epicenter of fashionable city life, as evidenced by the boutiques, cafes and bars on Rua Augusta and Rua Oscar Freire.
Some cities use everything about themselves as a marketing tool -- for example, the diverse heritage of Buenos Aires is no secret to people who live halfway around the world. Sao Paulo's pretty much the same -- it just never thought to tell anyone. The city's Liberdade district, all but adjacent to downtown, is home turf for Brazil's large Japanese community (nearly half a million live in the Sao Paulo area). You'll know you've arrived when the streets have "lanterns" hanging above them. The Japanese weren't the first to arrive -- the neighborhood was once Italian -- but today, that millions-strong community has moved on, and there's no mistaking which part of the world influences the atmosphere along the Rua Galvão Bueno. Stop in for some sushi and a snoop 'round; if you're about on a Sunday, the market in the square is a popular draw.
Say you visit Sao Paulo, or anywhere in Brazil for that matter. Chances are, what you're going to remember most vividly, will be the meat. (Well, that and the caipirinhas. Or, if you have too many, maybe just the caipirinhas.) Vegetarians are excused, but everyone else needs to pay a visit to at least one of the city's boisterous flesh parlors. This popular room just off Avenida Paulista features meat from the house ranch in the v. cowboy state of Mato Grosso do Sul. Help yourself to the buffet; satisfy your curiosity -- if any -- regarding feijoada, Brazil's No. 1 stew, right here, on Wednesday and Saturday nights (Alameda Santos 86).
Sitting on the same corner between the Luz train station and the leafy Higienopolis district since 1940, this is one of Sao Paulo's most time-honored places for a draft beer -- referred to here, and all over Brazil, as chopp (say: SHO-pe). Visited by all sorts of famous people (including, supposedly, soccer great Pele, but where hasn't he been?), this is where to dip into Brazil's German culture -- yes, there's sausage on the menu (Rua Aurora 100).
The debate over which is Sao Paulo's best pizza is pretty similar to that in the Northeastern United States, or, say, Naples -- its an argument that will never be finished. But the woodfired babies that come out of the oven at this Higienopolis pizzeria are a great place to start exploring just how much of an impact Italian immigration has made on the local culture (Rua Sergipe 406).
It seems slightly less cutting-edge six years after it debuted, but the Emiliano, with its zen interiors, Eames chairs, high-tech control consoles and pillow selections is still one of the best hotels in the city -- not to mention the host to an elegant French restaurant. Almost ideally located in the Jardins district, there's butler service, high thread-count linens and all sorts of other luxuries. The hotel, by virtue of being in Sao Paulo, is well-versed in making sure the needs of the business traveler are met -- from the complimentary welcome massage to the 24-hour fitness center and plunge pool up on the roof. There's even a helipad -- helicopters are a must-have for the richest of Paulistanos, who choose to avoid the traffic, accidents, crime and other inconveniences often found at street level. In fact, the city's per capita helicopter ownership is rumored to be the highest in the world. (from $470, emiliano.com.br).
Clubbish and retro-modern and yet wholly sexy decor set the stage at this warm Jardins property just steps from the Emiliano. It eschews modern cleanliness in favor of warm woods, leather and fabrics. Staff go out of their way to make you feel at home here. The restaurant, which preceded it, is one of Sao Paulo's favorite spots for seeing, beeing seen and nibbling on top-notch Italian specialties. Choose from 50 rooms and 10 suites, all fitted out with broadband, DVD players and flat-screen televisions, unwind at the rooftop pool and spa -- the view's as unforgettable as the hotel itself, which would be a credit to any world capital (from $440, fasano.com.br).
Refurbished and with a remarkable location just steps off the Avenida Paulista on the edge of the exclusive Jardins district and walking distance from Bela Vista, the Italian quarter, there won't be any surprises at this hotel, recently updated and refreshed in standard nouveau-Marriott style. But it's peaceful, the staff is on point and unlike in the flashier new chain properties over on the Rio Pinheiros, you're in an actual neighborhood -- handy for experiencing at least a little bit of the city if you've got scant free time. Spend about $60 more for a room on the club level for a more personalized experience -- not to mention great views from the lounge, free Internet and complimentary breakfast (from $275, marriott.com)
All inbound flights from the United States arrive at the distant Guarulhos International Airport, flights are spread out between Terminal 1 and 2. The airport has a utilitarian, concrete sort of vibe, and is not the sort of place that invites long-term lingering. United States residents will need a visa, obtained in advance. With that tucked away in your passport, you'll have no problems with Customs.
Navigating Sao Paulo on your own can be disconcerting, and while there are plenty of ways to do it, it would be foolish to say that anything other than a car and driver is best, particularly if you're here on business. Have your transport -- particularly in from the airport -- pre-arranged through your employer, client or hotel. Taxis are affordable, and plentiful at the airport.
Once acclimated and in your free time, it is perfectly fine to explore Sao Paulo's growing subway network. While it covers only a small part of the city, it is safe, cheap and swift, and connects the Jardins/Paulista area with the downtown in minutes. The system is in the process of expanding -- even an airport express line has been discussed. The system shuts down at midnight.
Like any foreign city, English is generally spoken in hotels, but quickly drops off once you head out of the building. Most people won't make assumptions as to your fluency in Portuguese based on your appearance -- this is a diverse city. Plan to pick up a few words of the local language. It'll help.
It may seem obvious to some, but to others, it can easily slip the mind: The language spoken in Brazil is Portuguese, not Spanish. (AWK-ward!) The city -- sometimes referred to as Sampa for short, but don't you start -- lies within Sao Paulo state, and unlike in New York, where you're technically a New Yorker wherever you live within the Empire State, residents of the city of Sao Paulo are known as Paulistanos, while state residents are referred to as Paulistas.
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