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Sao Paulo, Brazil

Sao Paulo isn’t for everybody. With a teeming population of 19 million, a sprawling, helter-skelter skyline that takes no regular shape, dozens of neighborhoods, and endless snarls of traffic, it’s easy to understand why tourists – especially first-timers to Brazil – head straight for the beaches of Rio de Janeiro.


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But for those willing to look beyond the chaos, and behind its gritty surface, Sao Paulo can be a sophisticated traveler’s paradise filled with chic little shops, innovative restaurants, and some mind-blowing hotels. Rio may have the beaches and the views – and the 2016 Olympics – but this stylish financial and business hub has plenty to boast about, including its status as a host city in next year’s World Cup.


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If you’re thinking of visiting, focus on South America’s winter months – June through August – when hotel bargains abound and weather hovers comfortably in the 60s and 70s. The occasional cold snap can send temperatures plunging into the 40s, so check the forecast, and be prepared to compete with the locals’ fashion-forward winter garb. Here are some of our favorite finds in this complicated, but incredibly rewarding city.

The Hotel: Hotel Unique
Hotel Unique

Designed in the shape of a boat (or maybe a giant slice of watermelon, depending on who you ask), the 5-star Hotel Unique, located in the city’s upscale Jardins neighborhood, is more than just an architectural wonder. Its rooms, which each feature a single, enormous round window, offer a serene, white-on-white escape from the city’s crowds. Attentive but unpretentious service and a killer rooftop bar (complete with a red-tiled swimming pool) make this the place to stay in Sao Paulo. (Av. Brg. Luís Antônio, 4700 – Jardim)

The Boutique: Adriana Barra
Adriana Barra

With everything from minidresses to surfboards printed in the designer’s signature flower patterns, the Adriana Barra boutique boasts the Brazilian designer’s vivid style on every surface. Pantone colors line the stairs and knick knacks (vintage china plates, a ukulele, a doll house) sit atop the clothing racks, turning the shop into an intimate exhibit of Barra’s personal collection. Be sure to check out the second floor, which sells (and is swathed in) Barra’s brilliant fabrics. (Alameda Franca, 1243 – Jardim Paulista)

The Neighborhood: Vila Madalena
Vila Madalena

Filled with easy going coffee shops, design boutiques, and vintage stores, this bohemian neighborhood also boasts the city’s best – and most ambitious – street art. On the day we visited, an artist was camped out on one of its side streets, adding a brightly spray-painted bird to the side of a Volkswagon bus. (We assume he had permission, given that he was being trailed by a fawning camera crew.) After a coffee at Ekoa Cafe, hang around to snap photos of the neighborhood’s rainbow-colored angels and demons, as well as the occasional glass mosaic, adorning its concrete walls and stairways. (West of the city center, on the #2 Metro line)

The Indulgent Dinner (With Drinks After): The Fasano
The Fasano

Located in Sao Paulo’s other it-hotel, the restaurant at The Fasano serves contemporary Italian cuisine in a hushed, dark-wood paneled dining room that’s sure to take the edge off a day of shopping in Paulista. Homemade pastas, excellent wine, and a gallant waitstaff ensure that no request goes unanswered – and that the bill will be enormous. If dinner is out of your price range but you still want a dose of the Fasasno’s sultry ambiance, head to the hotel’s back-room bar, where a band plays mellow jazz into the wee hours. We’re guessing you won’t even have to request “The Girl from Ipanema.” (R. Vitório Fasano, 88 – Jardim Paulista)

The Obligatory Stop: The Havaianas Store
The Havaianas Store

No visit to Sao Paulo is complete without a stop at the flagship Havaianas store on the city’s most bustling shopping street – Oscar Freiere. Choose from dozens of styles from this iconic flip-flop brand, or build a customized pair right in the store. Bonus points for the rainbow wall of flip-flops at the back, and the prices. In Brazil, a pair of Havaianas will cost you roughly half of what they would in the U.S. (R. Oscar Freire, 1116 – Jardim Paulista)

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