SEE While still wrought with contradiction--relatively high crime rates, but exceedingly warm and friendly locals--21st-century Sao Paulo is one of the most thrilling cities in the world. And Brazilians love their rock'n'roll, as evidenced by the successful 2012 debut of Lollapalooza Brazil (lollapaloozabr.com). This year's lineup is loaded with international superstars including the Killers, Nas and Franz Ferdinand; local hot shots; and exciting buzz bands like Foals, Alabama Shakes (whose Brittany Howard enthuses, "We plan to throw a big dance party!"), Toro y Moi and Two Door Cinema Club. The lattermost's Kevin Baird is excited to return to Brazil and play to fans that are "beautiful, bonkers and know how to party." When taking a break from the festival, check out the chic Jardins district, with its high-end designer shops and fashionable eateries, then hit the bohemian cool of Vila Madalena, rife with indie boutiques and alternative galleries like Choque Cultural (choquecultural.co.uk). For those seeking a respite from the bustle, the city's Parque Ibirapuera is a massive and stunningly beautiful green space-great for a peaceful stroll. But Foals' Jack Bevan also highly recommends "a day trip to the ocean, to see the turtles swimming." (The beach town of Santos, by the way, is just 50 miles away.)

STAY A post-millennial burst of cool boutique hotel openings hasn't been bettered, so the best have remained the best. Hotel Unique (hotelunique.com.br) couldn't be more perfectly named, with its wild half-moon shape. The rooftop Skye Bar (named for Morcheeba's Skye Edwards) has stunning views of the cityscape. Snoop Lion also digs it. The super chic Hotel Fasano (fasano.com.br) is celebrating its 10th anniversary, but is as sexy as when it debuted. (Coldplay and Britney Spears have stayed there.) It has two highly regarded restaurants, and is a genuine nightlife destination-especially its Baretto Londra Bar. Hotel Emiliano (emiliano.com.br), with its warm minimalist style and gorgeous pool, offers a more low-key, elegant cool.

EAT Brazil has a significant Japanese population, and Leo Ganem, CEO of GEO Eventos, which runs the festival, raves about Momotaro, which offers up "very modern Japanese food, with new presentations of sushi and sashimi." For a special experience, Lollapalooza Brazil promoter Helena Guimaraes says Spot (restaurantespot.com.br) "has a very fancy and cool crowd." The seafood is excellent but the people-watching while sipping a mojito is even better. For something equally hip but more affordable, she recommends the Mediterranean bistro Chez Lorena (chezlorena.com.br). Other dining hotspots include D.O.M. (domrestaurante.com.br), presenting an exalted modern take on Brazilian cuisine (with Amazonian botanical ingredients), and the charming Mani (manimanioca.com.br), which plays to the molecular gastronomy trend.

PARTY The Vila Madalena neighborhood is ideal for a groovy bar crawl. Ganem prefers "trashy places, where you can go in your shorts. So my favorites are Filial [barfilial.com.br] and Sao Cristovao." Brazilian singer Mauricio Pessoa says, "Bar Sarajevo [sarajevosp.com.br] is great for emo, punk, alternative jazz and Brazilian soul." For a "chope" Brazilian draft beer and authentic Sao Paulo music, he suggests Bar de Brahma (barbrahma.com.br). Meanwhile, D-Edge (d-edge.com.br) is a more high-concept, high-design nightclub, which Guimaraes insists "has the best sound system and best DJs," while the sexy Bar Secreto (barsecreto.com.br) pulls in the fashion crowd. But Lollapalooza Brazil manager Jonathas Vargas recommends just heading to the Baixo Augusta neighborhood to enjoy one of the many nightclubs of Augusta Street. Among those, Inferno Club (infernoclub.com.br) has great live music, while Studio SP (studiosp.org) is the place to dance.