36 Hours in São Paulo, Brazil

A CITY of high-rises and traffic jams in a country of rain forests and beaches, São Paulo, South America’s biggest metropolis, is a Brazilian freak of nature, except without the nature. But the city’s flaws — high prices, street crime, incessant drizzle — are no match for its strengths — artistic and business energy, relentless night life. Sometimes, it even manages to turn its flaws into assets, as when celebrated architects take ugly concrete and create post-Brutalist masterpieces, like Isay Weinfeld’s sleek bookstore Livraria da Vila on Alameda Lorena. São Paulo’s 11 million-plus inhabitants do their part by infusing the din with contagious Brazilian energy; those flashing smiles and thumbs-up signs are among the few things the city shares with the rest of the vast country whose booming economy it anchors.

Friday

3 p.m.
1) GRIMY GLORY

The elite may snap up luxury apartments as far from the heart of the city as possible, but São Paulo’s historic center still bustles with government employees and other office workers who have a nice secret on their hands. Sure, parts of the center could use a rinse in a giant urban bathtub, but much of the former glory is intact, including the city’s most beautiful art museum, the Pinacoteca (Praça da Luz, 2; 55-11-3324-1000; pinacoteca.org.br), housed in a former high school. Don’t miss the adjacent sculpture garden before hopping a subway to São Bento to get lost in the busy street commerce on Rua 25 de Março (25demarco.com.br) and stroll the pedestrian-only streets near the Centro Cultural Banco do Brasil (Rua Álvares Penteado, 112; 55-11-3113-3600; bb.com.br/cultura), a glorious old bank building turned exhibition space, where “Islam: Art and Civilization” is currently showing.

6 p.m.
2) COCKTAILS OR CAFFEINE?

When the business bustle dies down, make your way past the grand old Teatro Municipal (Rua Líbero Badaró, 377) toward one of the classic works by Brazil’s best-known architect, Oscar Niemeyer: the marvelously undulating 38-story Copan apartment building (Avenida Ipiranga, 200; www.copansp.com.br), now home to a diverse community of residents. Choose your pick-me-up at the ground floor shopping center: a creamy espresso at the old-school, standing-room-only Café Floresta, or a creative caipirinha cocktail at the classy and ballyhooed two-year-old Bar da Dona Onça (55-11-3257-2016; www.bardadonaonca.com.br).

8 p.m.
3) VERTICAL JUNGLE

Enough grime. Find the nearest ponto de táxi (taxi stand) and flee to upscale Vila Olímpia to dine with the elite at Kaá (Avenida Juscelino Kubitschek, 279; 55-11-3045-0043; kaarestaurante.com.br). Stepping through the barely marked entrance into the Arthur Casas-designed restaurant is like entering an alternative universe. The showstopper is the 4,300-square-foot vertical garden, a wall draped in plant species from the Mata Atlântica — the rapidly disappearing rain forest São Paulo used to be a part of. The contemporary menu — Brie tortellini with fig jam in sage butter, squid stuffed with crayfish and black risotto — is worth the steep price. (Dinner for two with drinks and dessert can approach 300 reais, about $185 at 1.63 reais to the dollar.)

11 p.m.
4) HOUSE PARTY

In Vila Olímpia, high-end nightclubs come and go, but the conspicuously consuming playboys and the surgically enhanced women they buy Champagne for are, alas, forever. Instead, head to Casa 92 (Rua Cristovão Gonçalves, 92, Largo da Batata; 55-11-3032-0371; casa92.blogspot.com), a new nightspot in what surely must have been the home of someone’s grandmother. As you wander from room to room and through the pleasant outdoor spaces, you might find yourself crashing a birthday party, striking up a caipirinha-fueled conversation or hitting the upstairs dance floor where recently formed couples make out.

Saturday

4 a.m. or 9 a.m.
5) BREAKFAST AND BED

Ending a long night on the town or starting a big day on the town at a padoca (the informal term for bakery) are two mutually exclusive São Paulo traditions. You can do either at Bella Paulista (Rua Haddock Lobo, 354; 55-11-3214-3347; bellapaulista.com), a padoca on steroids where the late-night crowd feasts on everything from pastries (very good) to oversize hot sandwiches (good) to salads (decent) to pizza (not so much). Starting at 7 a.m., there’s also a 26.90-real breakfast buffet, with breads and pastries, fruit, eggs and cold cuts. For a cheaper option, ask your hotel for directions to a neighborhood padoca and order fresh orange juice and a pão na chapa, a roll buttered and grilled until crisp.

11 a.m.
6) ART RUN

Plan a tour through São Paulo’s energetic gallery scene using the widely available, excellent Mapa das Artes. You might start at funky Choque Cultural (Rua João Moura, 997; 55-11-3061-4051; choquecultural.com.br), a crumbling old house that always has something surprising or provocative, then walk to the slick six-month-old Zipper Galeria (Rua Estados Unidos, 1494; 55-11-4306-4306; zippergaleria.com.br), which features 23 young Brazilian artists. A step up in class is Nara Roesler (Avenida Europa, 655; 55-11-3063-2344; nararoesler.com.br). Then hop a taxi just across the Pinheiros River to Galeria Leme (Rua Agostinho Cantu, 88; 55-11-3814-8184; galerialeme.com), housed in a contemporary São Paulo structure designed by the architect Paulo Mendes da Rocha. Note: those prostitutes hanging out on the nearby street corner are not a performance art installation.

2 p.m.
7) BIA AWAITS

Saturday is for feijoada, the classic Brazilian dish of black bean stew brimming with every part of a pig you can imagine. Feijoada da Bia (Rua Lopes Chaves, 105; 55-11-3663-0433) is hidden away in a homey setting in the Barra Funda neighborhood (but within walking distance of the Marechal Deodoro subway stop). It’s 62 reais for all you can eat — not cheap, but that includes an easygoing chorinho band, and possibly even free booze: recently, the owner, Bia Braga, has been doling out samples of her new house cachaça, produced by a family distillery in Minas Gerais state.

8 p.m.
8) THEATER SCENE

The language barrier may make seeing a play untenable, but that doesn’t mean you can’t dive into the hip alternative theater scene around Praça Roosevelt. Mingle with the pre- and post-theater crowd at nearby bars like Rose Velt (Praça Franklin Roosevelt, 124; 55-11-3129-5498; rosevelt.com.br), a cozy spot with quirky décor, like the patch of tiled São Paulo sidewalk on one wall. It carries Colorado-brand pale ale (brewed in São Paulo state), a nice change when the corporate swill you’ll get at most bars around town grows old.

Sunday

10 a.m.
9) ALL’S FAIR

Weekends bring out lovers of all things vintage to antiques fairs. One of the best starts at 8 a.m. on Sundays at Praça Dom Orione in the Italian neighborhood of Bixiga. It attracts a São Paulo mishmash of gay and straight, old and young, families and couples, all checking out old-fashioned cameras, antique walking canes and posters, and rummaging through piles of bossa nova LPs and vintage clothes. Several antiques stores also line the park to satisfy indefatigable shoppers.

12:30 p.m.
10) ARTFUL CUISINE

From afar, the red-striped skyscraper known as the Instituto Tomie Ohtake (Avenida Faria Lima, 201; 55-11-2245-1900; institutotomieohtake.org.br) resembles a contemporary tribute to the candy cane, though from street level, its oddball curves and colors become mesmerizing. And the creative range of exhibits inside — including paintings by the nonagenarian Brazilian-Japanese Ms. Ohtake herself — are well worth the trip. But the nearly 10-year-old institute just scored a game-changer: Santinho, a restaurant from the well-regarded chef Morena Leite. Ms. Leite, whose Capim Santo (capimsanto.com.br) has long been a stop for upscale Brazilian cuisine, has put together a super-fresh lunch buffet of gorgeous salads and cold dishes (from quinoa to banana and raisin to tuna tartare mixed with tapioca pearls), main courses (wild duck in blackberry sauce, the Brazilian classic dried beef with abóbora squash) and such desserts as crepe-like tapioca filled with the decadent cocoa-and-condensed-milk dessert called brigadeiro. It’s pricey (58.50 reais on Sundays), but the art is free.

IF YOU GO

Stay away from business hotels in South Zone neighborhoods like Vila Olímpia or Brooklin — they’re too far from the excitement. Big spenders will be taken care of at the Emiliano (Rua Oscar Freire, 384; 55-11-3069-4369; emiliano.com.br), a top boutique hotel, on luxurious Oscar Freire Street, home to some of the city’s best restaurants and shops. Rooms start at $570 — and there’s that convenient roof helipad.

An unconventional choice for those wanting to stay near the city center (but in a safe neighborhood) is the Hotel Pergamon (Rua Frei Caneca, 80; 55-11-3123-2021; pergamon.com.br), in Baixo Augusta. Pergamon, originally a boutique hotel, has morphed into a spot for small-scale business conferences. But its DNA is unspoiled: the lobby features Brazilian art mostly by artists from the northeast; the rooms have stylish touches, and many have skyline views; and the restaurant serves traditional dishes. Doubles start at 260 reais (about $160).