How Brazil’s ‘ugly sister’ might actually be its Cinderella city

It’s time for the usual layover in unloved, less-attractive Sao Paulo to be turned into a sleepover, says Chris Moss – just don’t expect much to get much shut-eye in this energetic metropolis

Sao Paulo is grey, unwieldy, busy – but with a beautiful side to discover (Getty Images)

The taxi is hurtling into town – but I’m not complaining. I’ve only got two nights and a day in São Paulo, so I need to squeeze the juice out of it. The road is absolutely rammed even though it’s late, dark, and drivetime is presumably over. Except it never is in South America’s megalopolis, famous for 100-mile traffic jams and the world’s busiest chopper lanes; helicopters are used by the rich when time is money. Suddenly, in the white beam of my cab, dozens of colourful lycra-clad bodies materialise. It’s a peloton, whizzing along what would be a bike-banning motorway anywhere else. They’re speeding home, helmets dipped, feet blurred in motion. I laugh. I can’t help but admire the night-riders.

“They go in big groups to avoid having their bicycles stolen,” says my guide, Edison, as if that’s obvious.

When I get to the hotel – the sumptuous Rosewood in Bela Vista – I feel like I’m walking late into a Gatsby-themed party. The bars and restaurants are throbbing. Women walk past reception dressed in feathers and spangly, otiose tops. I catch a snatch of torch song and follow the music to a dimly lit speakeasy packed with cocktail-tipping clients. The jazz is cool, smooth, mercifully not too bossa-inflected. But I’m bushed; I’ll save some energy for tomorrow.

The concrete heart of São Paulo is renowned for its ferocious traffic (Gabriel Ramos)

Daytime in São Paulo needs planning – and energy. I feast on granola and açai as fuel. The city covers almost 600 square miles; the metro area is five times that. If you (are a lunatic and) drive end-to-end it can take five hours. I have given Edison a challenge, though: I want to do some walking. He nods politely. He’s not convinced.

Still, off we set, down the Avenida Paulista. Most workers are already in their offices, but the wide pavement is busy and there’s a constant stream of black and silver cars. Paulistanos, the people of São Paulo city, pride themselves on their serious work ethic. Rio and Salvador, they say, are too busy partying and drinking Brahma beer and coconut milk.

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The architecture is riotous. I see Brutalist hulks, Modernist cubes, contemporary glass and steel towers, plus some early 20th-century houses, gradually being bullied out by developers. We pass the Edifico Gazeta, with its inclined mural and Eiffel Tower-inspired antenna; Daniel Libeskind’s voluminous Conjunto Nacional; the Unique hotel, which looks like a World War One tank crossed with a toy submarine. Communications, power, pretentiousness: all Paulistano virtues.

We walk for an hour – too fast and it’s hot – and I’m relieved to arrive at Parque Ibirapuera. This large green space would be called a lung anywhere else; here it’s just a couple of bronchi really. My visit coincides with the Sao Paulo Biennial, so I spend an hour gawping at multi-ethnic, inter-disciplinary, cross-cultural art. The biennial – housed in Oscar Niemeyer’s gorgeous pavilion – is the world’s second biggest, after Venice. Why don’t more Europeans fly in to attend?

Well, because Sao Paulo is a Cinderella city – overlooked in favour of beach resorts, Amazon cruises and wetlands wildlife holidays. It’s also considered an ugly sister: too grey, urban and heaving, especially for travellers who live in London, Paris or New York and feel they need a break.

Sao Paulo is a Cinderella city – overlooked in favour of beach resorts, Amazon cruises and wetlands wildlife holidays. It’s also considered an ugly sister: too grey, urban and heaving

In non-biennial years, there’s a huge amount of art still to see. The MASP (Museu de Arte de São Paulo Assis Chateaubriand) is Latin America’s best European collection, occupying a red concrete and glass masterpiece by Lina Bo Bardi. The Pinacoteca do Estado is the definitive collection of Brazilian art and sculpture, in a palatial 1900 building skilfully refurbished – or, more accurately, intervened in – by architect Paulo Mendes da Rocha.

For Braziian art, you can’t go wrong with the Pinacoteca do Estado (Getty Images)

It’s time for lunch so we jump in the car. The trip downtown gives me a window-view on the Art Deco municipal stadium (still used for home matches by Corinthians and Palmeiras football clubs), Niemeyer’s wave-shaped Edificio Copan and the striking, stylish Edificio Itália skyscraper. We hop into a lift to the 42nd-floor roof. I gawp and gulp at the most built-up panorama in the Americas: office blocks, apartment blocks, roads blocked, and runways, helicopter pads, vultures, trees, choppers.

Then I pig out on pig. Pork has always been my last-choice meat but A Casa do Porco, recently voted the top-ranking Brazilian restaurant (fourth in Latin America) in the annual 50 Best Awards, slow-roasts its joints to buttery perfection with sides of cassava croquettes, rice, beans and little salads.

We have coffee in Vila Madalena, a cobbled alley known for its lurid painted walls. I like the superheroes and big ideas, and there’s good stuff by renowned street artist Eduardo Kobra, but I’m more intrigued by the pinchaçao – angular cryptic writing, sometimes in seemingly impossible-to-reach sites. This is how favela-dwellers, gangs and activists communicate. The glyphs look like stick men or semaphores. I’m told they send messages of warning, violence and rage.

The graffiti district is trashy, touristy, very 2020s; youthful, middle-class slummers take selfies in the slanting afternoon sun with Batman rearing up behind them; their captions will be #glamGothamGarota, I suppose. But my next stop is classy and mid-century. Apartment 61 is a showcase and high-end shop for furniture and objets d’art. I fantasise about an expat lifestyle that’s thoroughly Modernist, minimalist and beige (in a good way), with the soundtrack of Morcheeba’s “São Paulo” echoing vapidly around my head. A Sergio Rodrigues chair costs £25,000. I get real and return to my hotel, where I take a sort of waking siesta. There’s a guitar on the wall signed by Gilberto Gil – who’s as famous here as Bowie is in the UK – and take it on to the balcony to pick a few notes. Amazingly, I am quite relaxed. I sound good. I take a beer out of the fridge. As dusk falls, I head to the terrace to sip a cachaça cocktail made with a fruit I’ve never even heard of; Brazil has dozens.

Street art features prominently in many districts (Getty Images)

Dinner at Taraz, the Rosewood’s South American eatery, is magnificent. My taste buds holiday in Peru, Argentina, Paraguay and Recife. Then it’s officially night. I have a drink each at Guarita, Guilhotina and Picco, three bustling bars all in Pinheiros – so not too much travelling. I stick to cachaça-based concoctions on the principle of not mixing, but the cane-based firewater can top 50 per cent alohol. By midnight, the bars are becoming clubs and the clubs are becoming hot and hectic. This ugly sister definitely turns it on late. I pop my head into one joint; it’s Eighties night. Before I can get nostalgic or, God forbid, start dancing, I remember I’m 57. I opt for jazz at the hotel. In the library I see a book with a cool cover and take it in. I find myself ordering a copy in parallel translation. Poetic inspiration? A mad impulse? Cachaça? Its English title is Hallucinated City. Jazz and literature and a nightcap: heaven, basically.

The next day I head for the coast – now in my own hire car. Lots of Paulistanos do this on weekends. The highway passes Interlagos, where Formula 1 races are run. I slip on my favourite Brazilian music compilation – Sampa Nova – and, at last, try to slow down. But the road is descending and the beats are frantic, incessant, insistent: pure São Paulo.

Travel essentials

How to do it

Humboldt Travel can arrange a trip to Brazil featuring two nights at the Rosewood São Paulo plus a full day’s guided tour of the city. The eight-night luxury holiday from the Brazil specialists also includes three nights in Rio de Janeiro at the Copacabana Palace with guided tours and three nights in colonial Paraty at the boutique Casa Turquesa. The holiday is priced from £3,750 per person including accommodation with breakfast, tours and transfers with English speaking guides. International flights are not included.

Getting there

Airlines including Latam and British Airways fly direct from London to São Paulo.

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