Sao Paulo gets a bad rap. Mention that you're visiting, and the best you're likely to get is a raised eyebrow and a "will you have time to go to Rio afterwards?" You can see why: sights are few and far between, public transport is inadequate and "Sampa", as locals know it, lacks the slow, sultry charm of its prettier sister, 200 miles up the coast. But in spite of all that, this city of 20 million people – the third largest metropolis in the world, and Latin America's economic powerhouse – buzzes with creativity, progressive thinking, and, now more than ever, prosperity.
But rather than skyscrapers and sleek restaurants, I'd come to see the city's street art. In this unapologetically gritty city, it's unsurprising that it has one of the most vibrant street art scenes in the world. A celebrated part of the city's culture, the arte urbana movement has seen homegrown names such as Os Gemeos ("the twins") and Nunca emerge from their working-class roots here to end up exhibiting at Art Basel Miami and London's Tate Modern.
You'll find graffiti on walls all over town, from crude pixacao – a black, angular style of tagging born in Sao Paulo that now, somewhat unpopularly, daubs walls all over the country – to huge colourful pieces beloved of Paulistanos, the city's residents, and protected by the city council.
The best place to see great street art is Vila Madalena, the beating heart of bohemian Sao Paulo. It's an area whose bright low-rise houses and winding lanes are the antithesis of the sky-scraping avenidas you'll find a couple of miles east in the city's centre.
Choque Cultural, at Acervo da Choque, 250 Rua Medeiros de Albuquerque (00 55 11 3061 4051; choquecultural.com.br) is a small gallery that has become a global ambassador for street art since it opened in 2003 and one of its founders, Baixo Ribeiro, had offered to show me around the neighbourhood. We wandered a block south and turned right into Beco do Batman, or "Batman alley". The stencil of the Caped Crusader that gave the cobblestone lane its name in the 1970s has since been painted over, but now every conceivable space is covered in graffiti.
At the end of the alley we emerged on to Rua Harmonia, and at the end of that Rua Aspicuelta, Vila Madalena's main thoroughfare. It's full of one-of-a-kind cafés, restaurants and quirky shops. None quirkier, surely, than Preta Pretinha at number 474 (00 55 11 3031 5385; pretapretinha.com.br), the project of three local sisters who, when they were growing up, couldn't find dolls that reflected their Afro-Brazilian heritage and so began making their own. Now the shop sells a diverse collection including indigenous South American, blind and wheelchair-using dolls.
We doubled back half a block and turned on to Rua Fidalga and into another business born of the local street art scene at number 66, Vertices Casa (00 55 11 30 62 8499; verticescasa.com.br), an artist collective's shop selling prints by local and international street artists as well as jewellery. To see where street artists master their art, Baixo lead me one block down onto Padre Joao Goncalves and left at the blink-and-you'll-miss-it entrance to Beco do Aprendiz, or "learners' alley". This open-air art gallery or "wall of fame" used to be rife with drug dealing, but now pieces by local and international artists, including Paris's Invader and New York's Swoon, cover every inch of the pavement and walls. Often derided for being an ugly city, Sao Paulo banned "visual pollution", which meant all outdoor advertising, as part of a "clean city" law passed in 2006. It was a popular but controversial move. "A lot of people lost their jobs", Baixo told me, "but on the other hand it opened up space for street art, which began to appear a little more".
Initially graffiti was banned as part of the clean-up, but after a public outcry the laws concerning street art were relaxed and murals began to take over spaces once occupied by advertising. I asked Baixo if he thought street art would entirely take the place of the hoardings that came before? "Yes, I do," was his surprising reply. To contemplate what Piccadilly Circus, for example, might look like with murals rather than billboards, we headed to Café Aprendiz (186 Rua Belmiro Braga; 00 55 11 3819 1035; cafeaprendiz.com.br) at the top end of the alley for a coffee.
Sated, we continued down a block and left onto Cardeal Arcoverde and through Sao Paulo cemetery, whose walls are covered in framed, elaborate versions of pixacao. Here these usually grubby-looking tags form part of an art project that invited local children to decorate one of the walls.
We emerged on to Rua Henrique Schaumann where 10 lanes of near-gridlocked traffic typified modern-day Sao Paulo. Safely across, we were back once again in alternative environs, this time in Praca Benedito Calixto, with its buzzing Saturday flea market. But of more interest was Choque Cultural's other gallery (997 Rua Joao Moura; 00 55 11 3061 4051) a block east from here, which sells work by local artists.
Here, the urban creative vibe ends and hip, arty Sao Paulo creeps into hip, loaded Sao Paulo. We wandered one block down onto Rua Teodoro Sampaio, which is crammed with musical instrument shops, and then turned right onto Rua Oscar Freire, a swanky avenue lined with boutiques and international brands, which we followed until we reach a gleaming white Havaianas flip-flops store, complete with valet (00 55 11 3079 3415).
The shift in ambience was palpable – we were now in Jardins, Sao Paulo's poshest postcode. To see where all those Brazilian reals are being spent, I pulled up a chair outside the Santo Grao café at no 413 (00 55 11 3082 9969; santograo.com.br), where I had a vantage point of one of South America's most expensive hotels, the shimmering, sleek Emiliano (00 55 11 3069 4369; emiliano.com.br). I might have only been half-an-hour's walk from the can-sprayed cool of Vila Madalena, but this part of Sao Paulo might as well have be in a different continent – as I glanced up, glinting in the sky, was the Emiliano's helipad.
The latest venture from Chez, the trendy Franco-Brazilian group that has a clutch of bars and restaurants here, is Chez Mis (Avenida Europa 158 Jardim Europa; 00 55 11 3467 3441; chez.com.br). It's been a hit with the cool crowd since it opened earlier this year, serving Mediterranean-inspired comfort food in the sleek, verdant surrounds of the Museum of Image and Sound.
Sao Paulo has the largest Japanese community outside of Japan, mostly found in the Liberdade district. Here, you'll find good sushi on virtually every corner, but the current buzz is all about Momotaro (591 Rua Diego Jacomé; 00 55 11 3842 5590; restaurantemomotaro.com.br).
Patrick Welch travelled with Journey Latin America (020-8747 8315; journeylatinamerica.co.uk), which offers a 15- day trip in Brazil visiting Rio, the Iguacu Falls, Salvador and Sao Paulo from £3,203pp. The price includes international flights from London, transfers, domestic flights, B&B accommodation and excursions including a walking tour in Sao Paulo. Sao Paulo is served by British Airways (0844 493 0787; ba.com) and TAM (020-8897 0005; tam.com.br) from Heathrow.
Paradiso (00 55 11 7587 0747; paradisohostel.com; vitorrolim.wordpress.com) is a budget, street art-inspired hostel in Vila Mariana, run by local artist Vitor Rolim and two of his friends. Double rooms at its new guesthouse annex start at R$120 (£37), room only.
Sao Paulo Tourist Office: spturis.com