The Best of São Paulo in 72 Hours

by Dan Allen
Friday Mar 29, 2013

"You have been to Sampa before?" the man asks, turning to stare straight into my eyes. "Ah no, first time," I answer. "But very excited." The man turns away again, and I take a quick deep breath. "Oh, my friend, you will absolutely love this city," he says, swerving to look directly at me again. "She is like no other in the world. She is alive."

Part of me is thrilled that the first guy I meet in São Paulo is such a passionate fan of his hometown. A bigger part of me wishes that he wasn't my cab driver, who's paying far more attention to me in the back seat than he is to the busy city highway that we're speeding down. Great that São Paulo's alive; not so sure how long I'll be anymore.

I survive, and my white-knuckled ride into town from the airport proves to be a great introduction to thrilling São Paulo, so full of passion and excitement, with just a hint of danger thrown in to keep things interesting. Sampa - as the 11.5 million locals call their vast hometown - is the biggest city in Brazil and all of South America.

This isn't the Brazil of Rio, with lazy sunny beaches and endless samba music. This is the Brazil of fashion, culture, commerce and a fast-paced global flair. It's a wildly diverse and cosmopolitan mega-city that you couldn't possibly get to know fully in three days - but you can sure have a lot of fun trying.

Day 1: Spectacular Views

Check into the Pergamon Hotelon Rua Frei Caneca, right on what’s known to Paulistanos as "Gay Caneca," thanks to its many LGBT venues. The Pergamon offers a nice boutique style at reasonable rates, and it’s also well situated for touring the city - not only close to the gay stuff, but also some of Sampa’s most important mainstream attractions.

In a sprawling city like São Paulo, it’s crucial to get your bearings. Head downtown to the absolute middle of the city at Sé Square (Praça da Sé), the site of some of its most important historical events.

At one end is São Paulo Cathedral - the current structure dates only from 1954, but it’s on the site of the 16th century church that served what was then a small village. Nearby is the interesting Solar da Marquesa de Santos, the well-preserved mansion of a rather notorious 19th century noblewoman, who also happened to be the lover of the Brazilian emperor. A few blocks to the west is the striking neo-classical Theatro Municipal (Municipal Theatre), a hub of the São Paulo’s cultural life for more than a century, and where such global greats as Rudolph Nureyev, Enrique Caruso and Vivien Leigh have performed.

For lunch, head to the Mercado Municipal (Municipal Market), the city’s best-known and most important traditional market. Known just as Mercadão to locals, the market dates from 1926, and sells a staggering 450 tons of food every single day. Grab one of Mortadela Brasil’s signature massive sandwiches then work it off by wandering the market’s nearly 300 stalls spanning more than 135,000-square-feet. Don’t miss Casa da Moça, offering some of the freshest and most delicious exotic Brazilian fruits you’ll ever taste, short of picking them yourself.

Now that you’ve seen the city’s heart, you’re ready for a breathtaking glimpse of its whole body. On República Square you’ll find the city’s second tallest building, Edifício Itália. Elevate yourself up to the 44th floor, where you’ll find the incredible Terraço Itália, a gentleman’s club-like lounge that’s home to some of the most incredible views you’re likely to experience anywhere in the world - a mind-boggling expansion in all directions. It’s simultaneously magical and humbling, a feeling best savored over one of the Terraço’s yummy (if not cheap) cocktails.

After a disco nap back at the hotel, head down Frei Caneca a few blocks to Tirreno’s to get skewered right in the middle of the gay quarter. Serving a cute young crowd, Tirreno’s specializes in stick-bound foodstuffs of all sorts, from fruits and vegetables to grilled meat.

Afterward, head back to hip gay hotspot The Society, conveniently located just around the corner from the hotel. Owned by the same folks that run the crazily successful The Week (where you’ll go tomorrow night), The Society is located in a luxurious former mansion and draws one of the city’s coolest and sexiest clienteles.

Next page for days two and three!

Day 2: Culture Shock

Today is all about São Paulo’s incredible art. Hop in a taxi and head south to Parque do Ibirapuera, a huge green space of approximately 17-million-square-feet that includes several of the city’s top attractions, many of them in buildings designed by famed Brazilian architect Oscar Niemeyer.

First stop is the Museo de Arte Moderna (MAM), which houses more than 5,000 works of modern and contemporary art, and has hosted acclaimed shows by international gay art darlings like Wolfgang Tillmans. This year, photographer Christopher Makos’ fabulous "Lady Warhol" exhibition runs April through June, intimately capturing Andy Warhol’s transformation into his drag alter ego during a 48-hour period in 1981.

For lunch, pop into the museum’s cool Prêt, serving a fresh and delicious blend of Brazilian, French and Italian cuisines. Next, head across the park to the fascinating Museo Afro Brasil,which showcases the myriad contributions of African-descended Brazilians to the country’s history, culture and identity.

One more stop before you can hit your museum wall: the spectacular Museu de Arte de São Paulo (MASP) back toward the city center on Avenue Paulista (the home street of the city’s massive gay pride parade in June, the biggest in the world with more than 3 million participants). MASP’s striking glass building - seemingly hovering in midair over a concrete plaza that hosts an antique fair on Sundays - is not to be missed. Here you’ll find the strongest and most comprehensive collection of Western art in Latin America, from Rubens to Gainsborough to Picasso.

Take a break, then head out to dinner in another of São Paulo’s most recognizable buildings: the ultra-chic Hotel Unique, which quite uniquely indeed resembles a slice of watermelon. On the roof, you’ll find the excellent contemporary-cuisine Skye restaurant and bar, complete with a dreamy pool, amazing views, and one of the hippest mixes of moneyed locals and tourists.

Then it’s time for the city’s most must-do gay event of the week, fittingly called The Week. Unless you know someone, you’ll have to join the locals in the queue to get in, but it’s well worth it: This is the biggest gay dance club in South America, with two huge dance floors plus an outdoor pool area, and a crowd that’s simply hotter than hot.

Day 3: Retail Therapy

After a busy couple of days of exploring and cavorting, you’ve earned a Sunday of laid back shopping. Just down the street from your hotel is Shopping Frei Caneca, widely claimed to be São Paulo’s gayest mall. There is indeed a fair amount of boys and 140 shops here, but frankly, none that are all that special. A much better selection is several blocks onward along Rua Oscar Freire, the city’s premier shopping street. Here you’ll find the usual top international labels like Marc Jacobs, Armani and Dior, as well as Brazilian brands like Alexandre Herchcovitch, Osklen, and the world flagship store of the iconic Havaianas footwear line.

Grab lunch at the nearby Obá, a tasty blend of Brazilian and Mexican with bits of Italian and Thai thrown in for good measure, all in a colorful and arty yet warm and homey setting.

Then it’s on to more shopping - grab a cab and head over to the Vila Madalena neighborhood, known for its bohemian vibe and eclectic shops (like the cool kitchenware at La Da Venda). Don’t miss Beco do Batman (Batman Alley, or officially Rua Gonçalo Afonso), the area’s famous and ever-changing roadway lined with gorgeous street art.

Drop your packages back at the hotel, then head over to Vermont Itaim to join the ladies (and a few hot queer boys) for some boisterously fun early evening lesbian samba. Once you’ve worked up an appetite, there’s no place in town better suited to sate it than the nearby Jardineira Grill, one of Sampa’s top churrascarias (Brazilian steakhouses). Jardineira’s upscale vibe has been drawing Brazilian and international celebrities for decades (as evidenced by the totally fun hall of fame lining the way to the loo), and the nonstop onslaught of tasty grilled meat will put you in the perfect food coma for your flight home.

To find out even more about São Paulo, check out city’s official tourism site and its LGBT visitors brochure.

Dan Allen covers travel and gay culture for numerous outlets around the world including, Yahoo Travel, Queerty, Westways, Passport, The New York Post and Private Islands.


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