Even through jaded adult eyes, the first glimpse of São Paulo from the air is both exciting and intimidating. For a child, the responses are amplified. Young eyes have never seen so many skyscrapers, a bristling carpet of concrete and glass that stretches to the smoggy horizon.

Stark facts compound the unnerving sense of awe. This is the largest city in the Americas, the largest in the Southern Hemisphere and, by some counts, the third-largest in the world. For arriving families, the first question when faced with this overwhelming megalopolis is, “Where do we start?”

The answer is mundane. You’ll inevitably start in a vehicle. Get used to it. During any tour of São Paulo you will unavoidably spend a hefty proportion of your day driving from one part of the city to another, shuffling block by block in glacial traffic. Make sure iPads or MP3 players are on hand to stave off boredom.

A logical initial destination is Praça da Sé, the palm-lined square in front of the twin-spired Metropolitan Cathedral. In the center of the square is a squat pillar marking Point Zero. All measurements for the city, and for the wider state of São Paulo, are calibrated from here. If you lift your children onto the pillar, you give them temporary dominion over São Paulo. What better way to begin a visit?

The cathedral itself, with seating in the nave for 8,000 people, is an impressive edifice. On a sunny day (not that common in drizzly São Paulo) the stained glass windows bathe the interior in colored light. Given the city’s long history, the cathedral is not as old as you might expect. The main part was completed in 1954, and finishing touches were being made up to 2002.

A short walk to the north is Pátio do Colégio (the School Yard), the exact spot on which the city was founded Jan. 25, 1554. You need considerable imagination to picture the scene then, when this place was nothing more than a small hill amid unbroken rainforest. It was here a band of Jesuits built a simple school that gave rise to a church that gave rise to a Jesuit community that gave rise to Brazil’s biggest city.

Having visited the geographic heart of São Paulo, followed by the historical heart, it is just another short journey north to reach the living heart, the Municipal Market, a place pulsing with scents and sounds. Occupying an ornate 1930s building, the market is a hub for produce from all corners of Brazil. Some of the foodstuffs will be familiar; others (especially fish from the rivers and fruit from the rainforest) will be completely alien.

A city as cosmopolitan as São Paulo is always likely to produce a few surprises to throw new visitors off balance. The district of Liberdade, south of the Metropolitan Cathedral, is one such surprise. On the narrow street of Rua Galvão Bueno, you pass beneath a red ceremonial arch and instantly leap to the other side of the world. The streetlights are designed like Chinese lanterns, there are Oriental touches to many of the buildings, and shop signs are in an impenetrable script.

Japanese influence in the Liberdade neighborhood © Aguina | Dreamstime.com

You have stumbled into the largest Japanese stronghold outside of Japan. São Paulo is home to more than 660,000 people of Japanese descent; and although many speak Portuguese as their first language, they maintain cultural links with their ancestral home. For children with a love of manga comics or Hello Kitty, Liberdade is a must.

Throughout your time in São Paulo, you will often find yourself intersecting, or traveling along, Avenida Paulista, the city’s answer to Fifth Avenue or the Champs-Élysées. Once lined with the mansions of the Brazilian coffee barons, this broad avenue now passes between gleaming corporate high-rises. São Paulo accounts for a third of Brazil’s gross domestic product, and Avenida Paulista is where that wealth is most conspicuously proclaimed.

Halfway down Avenida Paulista there is another of São Paulo’s surprises. Concrete suddenly gives way to greenery. The taste of pollution is masked by tropical blossom. This is Parque Trianon, an unlikely sliver of rainforest in the middle of the city. Look carefully into the canopy and you might even spot marmosets — tiny monkeys — scampering among the branches.

Opposite the park is the striking São Paulo Museum of Art, or MASP, a 1960s Brutalist building surreally suspended off the ground on red legs. The museum’s collection includes important paintings by Velázquez, El Greco, Van Gogh and Picasso.

For an artistic experience of a completely different kind, head to Rua Gonçalo Afonso in the district of Vila Madalena, west of downtown. Better known as Beco do Batman (Batman Alley), the walls and sidewalks have become an impromptu graffiti gallery, with a half-mile of work by amateurs and internationally recognized artists. If your kids are artistic, bring some spray paint. The gallery is constantly evolving, and anyone can contribute.

Another epicenter of urban culture is found a short distance away at Parque Zilda Natel off Avenida Doctor Arnaldo, where a rundown street corner transformed into a skate park with bowls, tracks and pipes suitable for skateboarders of all abilities. It’s a great place for visiting children to forge new friendships. Adults can fill in time by crossing the road to explore the expansive Araca Cemetery, the final resting place for some of São Paulo’s most notable inhabitants. Some of the tombs are the size of houses.

A more conventional attraction is located in the southern part of the city. São Paulo Zoo, which is home to more than 3,000 animals, provides an interesting introduction to Brazil’s native fauna alongside species from around the globe. On weekends, this is the perfect venue to mingle with ordinary Paulistanos (as residents of São Paulo are affectionately known).

There is one aspect of Brazilian culture that transcends all others. You can never really know this country, or the city of São Paulo, without embracing soccer (futebol). Alongside Catholicism, it is the national religion. There are several professional clubs in the city, including São Paulo FC, Palmeiras and Portuguesa. The Corinthians, reigning World Club Champions, currently eclipse them all.

Soccer fever is likely to increase — if that’s possible — in the run-up to the 2014 FIFA World Cup. The Corinthians’ new stadium, which features the world’s largest TV screen and seating for 68,000 spectators, will be one of the main venues. Check the club website for upcoming events. You haven’t truly been to São Paulo until you’ve been to a soccer game.

At first sight, São Paulo does not appear welcoming to visitors, and certainly not to those with families. It’s huge, it’s crowded, and it never pauses for breath. And yet, as you get to know it, it opens up. There is something for everyone here. You arrive as strangers, but you leave as Paulistanos.

Where to Stay in São Paulo

Hotel Novotel Center Norte This family-friendly hotel is situated next to a shopping mall north of downtown. Family rooms are available; children under 16 stay free. Ave. Zaki Narchi 500, Vila Guilherme $$

Hotel Unique The name says it all. Shaped like a boat, with porthole windows, nowhere else looks quite like it. A fun place to stay. Ave. Brigadeiro Luis Antonio 4700, Jardim Paulista $$$

Renaissance Hotel São Paulo The Renaissance has an excellent location close to Avenida Paulista. Families are welcome; babysitting services are available. Alameda Santos 2233 $$$$

Restaurants in São Paulo

Bar Mortadela Brasil Located in the food court of the Municipal Market, this eatery serves famously gigantic bacon and cheese sandwiches. Municipal Market, Rua da Cantareira $

Famiglia Mancini Cantina When in São Paulo, eat pizza. Seriously. Only Rome and Milan have more Italian inhabitants than São Paulo. Many eat here. Rua Avanhandava 81, Centro $$

Figueira Rubaiyat Constructed under and around a giant fig tree, this popular restaurant is particularly renowned for its Brazilian steaks. Rua Haddock Lobo $$$

São Paulo Info to Go

International flights arrive at São Paulo Guarulhos International Airport (GRU), by far the busiest airport in South America, located 16 miles northeast of downtown. Although there are plans to link the airport to São Paulo’s subway system in the future, for now the main transport options into the city are shuttle bus or taxi.