After a wild Carnival week in Rio de Janeiro, and before heading south to Santa Catarina, we figured we might as well make a pit stop in São Paulo. A lot of fellow travelers in Brazilian forums didn’t have kind words for the city and flat-out advised against it. But since it was right on our way, we thought, “Why not?” In the end, we stayed for three full days—and honestly, we had a pretty fascinating time. In this post, I’ll share the highlights of our stay, which might come in handy if you’re also thinking about giving São Paulo a shot.
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Day #1: Settling in & Wandering Downtown
We rolled into São Paulo at dawn, groggy from an overnight bus ride out of Rio. After killing a few hours loitering around the terminal like professional drifters, waiting for check-in time, we finally hopped in a taxi to our hotel. A few blocks before arriving, it suddenly clicked why the place seemed like such a bargain for something that looked so upscale online—turns out, it was smack in the middle of Cracolândia, São Paulo’s infamous open-air crack market.
Rather than being daunted, we were genuinely intrigued. It felt like a prime opportunity to experience something off the beaten path. I’ve written specifically about our time in Cracolândia here, in case you’re curious. And if you’re not easily appalled by a bit of misery and chaos, you might want to check out Hotel Piratininga when visiting São Paulo—it’s an exceptional bargain. But if you’d rather stay in a safer and more polished district, have a look at the accommodation options on the handy map below.
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After settling in and lolling around for a bit, we headed out in the afternoon for an introductory stroll through Brazil’s principal concrete jungle. Passing the junkie-inundated, squalid streets of our neighborhood, we reached the bustling and surprisingly neat city center. Here are some interesting spots we came across during this first short walk.
São Bento Monastery & Square
First was São Bento Monastery (location) and its namesake square, a surprisingly serene pocket amid the city’s usual frenzy. The monastery itself, towering and stoic, looked like it hadn’t flinched since the colonial days. Founded by Benedictine monks back in 1598, the monastery has somehow survived centuries of urban madness, standing today as a massive, almost intimidating building with a distinct neo-Gothic facade. Inside, it still functions as an active monastery and is famous for its Gregorian chant masses. The square outside hosted a mix of hurried office workers, wandering tourists, and a lunatic preacher shouting into the void.
Altino Arantes Building
A few blocks later, we stumbled upon the Altino Arantes Building (location), better known as the Banespa—São Paulo’s very own wannabe Empire State Building. Once the tallest skyscraper in Latin America, this Art Deco giant was built in the 1940s and still towers proudly over the city’s chaotic skyline. For a fee, it’s possible to ascend to the building’s observation deck, known as Farol Santander, for a sweeping panorama of São Paulo.
Avenida São João Outdoor Watering Hole
Walking down the pedestrian street of São João from the skyscraper, we stumbled upon a makeshift outdoor bar (location)—a cluster of plastic tables scattered in front of a couple of beer shops. Despite being wedged right into the city’s business district, the place was packed with stoners casually smoking weed out in the open, while psytrance thumped from one of the shops like it was the most normal thing in the world. Naturally, we stopped for a drink.
Anhangabaú Promenade
Slightly tipsy and merrier, we drifted into the Anhangabaú Promenade (location). Its Portuguese/Tupi-Guarani name, Vale do Anhangabaú, means Valley of the Bad Spirit’s Water and refers to the river that is now buried under tons of concrete and slabs that form an elegant pedestrian esplanade. A long open stretch wedged between the city’s towering civic buildings, once a neglected underpass zone, it’s been spruced up into a human-friendly space with fountains, trees, and public benches. Still, the grit lingers in a way that feels honest—buskers with cracked amps, bored teenagers boozing and blasting funk, and a small army of skaters using the stone benches like a skatepark.
Just as dusk settled in, we wrapped up the day with a biryani and a lassi at this backstreet Indian restaurant, then made our way back to the hotel through the now-dark, squalid streets of Crackland.
Top Tours & Activities in São Paulo
Day #2: Mainstream Sightseeing
After a hefty hotel breakfast a coffee on the pavement amid waking crackheads, we headed out early to explore some of São Paulo’s most notable sights. Here are the highlights.
Municipal Market of São Paulo
We started with the Municipal Market of São Paulo (location), known locally as Mercadão. Housed in a grand 1930s building with stained-glass windows and soaring ceilings, it’s the kind of place that manages to feel both chaotic and oddly dignified. The ground floor is a sensory overload of tropical fruit stands, barrels of bacalhau, and butcher counters selling things we couldn’t quite identify. Lunch counters served some absurdly large mortadella sandwiches—they seemed to hold a competition as to how many layers of mortadella they could fit between two slices of bread before it breaks apart—which are pretty much the market’s unofficial rite of passage.
More than an actual market—where any local of any income might actually shop—the place was a full-blown tourist trap. Having ignored a few, we ultimately gave attention to one of the insistent touts of a fruit stall. He practically forced-fed us samples of his entire inventory, theatrically mmming palatal satisfaction like a food YouTuber on our side. In the end, he reluctantly stopped filling a huge plastic platter for our purchases at a literal handful of dates and strawberries. He tried to charge us 15 euros for that. We could hear him lowering the price by 10 reais at a time as we walked away, empty-handed and without saying a word.
José de Anchieta Basilica
Not far from the market, tucked behind a busy square, we found the José de Anchieta Basilica (location)—one of São Paulo’s oldest religious sites. Originally part of the Jesuit college founded in 1554, this spot marks the exact place where the city was more or less born. The current structure is a modern reconstruction, but parts of the original colonial walls are still visible if you look closely. It has a quiet vibe, strangely out of sync with the surrounding city noise.
Sé Square and São Paulo Cathedral
A couple of blocks south of the basilica, we stepped onto Sé Square (location), São Paulo’s symbolic center and home to the city’s main cathedral. The square was buzzing, though not exactly in a cheerful way. A long, swerving queue of destitutes had formed before a charity food handout. Nearby, office workers and street kids moved around each other like they were in separate dimensions. The cathedral loomed above it all—massive, neo-Gothic, and a little grimy, with palm trees lining the square like guards on break. We stepped inside for a moment of shade and silence, while outside, life kept unfolding in a way that felt both ordinary and overwhelming.
Liberdade Japantown
By noon, we reached Liberdade (location), São Paulo’s Japanese district—or at least what started as one. These days, it’s more of a pan-Asian free-for-all, with Japanese lanterns lining the streets, but also Korean pop stores, Chinese herbal shops, and Thai noodle joints crammed side by side. We passed anime shops and murals of Pokémon and Dragon Ball characters towering over alleyways. Storefronts decked out in Hello Kitty merch like it was still 2005. The air smelled like grilled yakitori and bubble tea syrup, and every third place seemed to sell sushi by the kilo. The place was a bit kitschy and chaotic, but full of character. We stopped for an Asian lunch, and resumed our walk.
Oriental Garden
By the main entrance to Liberdade lies the Oriental Garden (location). It felt like a brief timeout from the district’s sensory overload. It’s a small, landscaped pocket with koi ponds, stone lanterns, and a red arched bridge that people line up to take selfies on. While the garden was clearly designed to evoke calm, it couldn’t quite shake the background noise of traffic and street vendors yelling. Still, for a few minutes, we sat under a tree and watched kids toss crumbs to the fish like it was the most important thing happening in the city.
Municipal Theater of São Paulo
Circling back toward the center, we passed by the Municipal Theater (location), one of São Paulo’s more surprising landmarks. Built in the early 1900s in full European opera-house fashion, it looks like someone dropped a slice of Paris into a Brazilian plaza. The building has hosted everything from highbrow operas to early 20th-century anarchist meetings, which somehow feels fitting. You can join a free guided tour if the timing works out, but even just seeing it from the square is enough to make you wonder how it ended up there.
Church of Our Lady of the Rosary of Black Men
Standing in the middle of Largo do Paiçandu Square, the Church of Our Lady of the Rosary of Black Men (location) is easy to overlook—modest in size and painted a warm ochre yellow under the defacing graffiti on its base, it doesn’t call much attention. But its history runs deep: built by and for formerly enslaved Afro-Brazilians in the 18th century, the church was a spiritual refuge at a time when they were excluded from white churches. Inside, the decoration is simple, but the meaning is heavy; it’s one of the few surviving spaces in the city directly tied to the Black resistance of that era.
Evangelical Lutheran Church of São Paulo
Lastly, we came across the Evangelical Lutheran Church of São Paul (location). Built in the early 1900s by German immigrants, it stands out with its clean lines, pointed spire, and a calm, almost austere vibe that feels very un-Brazilian in this part of town.
Grassroots Samba Gig
After an afternoon rest, we went out again in the evening, looking for some night fun. Just around the corner from our hotel, we stumbled into a lovely bar (location) where a live samba jam was about to begin. We grabbed a beer, accepted a few tokes from the spliff the owner kindly passed around, and sat at the sidewalk tables to enjoy. The band squeezed into a corner—a circle of musicians banging out rhythms on pandeiros and cavaquinhos while regulars sang along between swigs of beer. It soon got loud and busy with denizens and crackheads dropping in to either dance or beg—depending on whether they were high or in cold turkey. We stayed late and crashed after a grub from the after-hours restaurant next door.
Day #3: Roaming in Cracolândia and Parque da Luz
On our third day in São Paulo, we didn’t venture far from our hotel. We spent much of the day wandering through Cracolândia’s dilapidated and misery-drenched streets. The area is infamous for its open-air drug scene, and nothing about that reputation is exaggerated. We walked and observed, unsure whether to feel like witnesses or voyeurs. As I’ve already mentioned, if you’re curious about what that walk was like, I’ve written a more in-depth post dedicated to our experience in Cracolândia.
For a break, needing some space to digest it all, we cut through to Parque da Luz (location) just a few blocks away. That’s the city’s oldest public park and feels strangely elegant considering how close it sits to the chaos. There were trees full of birds, old men sketching in notebooks, and the occasional couple taking selfies by the sculptures. Nearby, we had lunch at this lovely café with an adorable bulldog for a mascot.
On the following day, we chilled in the hotel room and lobby after checkout, killing time before catching our night bus to Florianópolis.
Photos
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