The twin spires of a neo-gothic church rise up into the sky amidst other less dramatic buildings.

The Catedral da Sé is large enough to hold 8,000 people. Photo © Bruno Padilha, licensed Creative Commons Attribution.

São Paulo has undergone immense transformations since its foundation in 1554. However, hidden away in its original downtown core are a few interesting vestiges of the city’s colonial past, which are all the more striking for being hemmed in by a forest of skyscrapers. Although you should always be on the alert for pickpocket types, wandering around Centro during the day is a fairly safe, if mildly chaotic, experience. At night, however, much of the area clears out, making taxis necessary. The geographic, historic, and symbolic center of São Paulo is Praça da Sé. By day, this vast plaza is filled with thousands of Paulistanos hurrying to and from somewhere, along with camelôs (illegal sidewalk vendors) hawking cheap wares and small clusters of street kids. It is here that many protests and demonstrations have been held—one of the most famous occurred in 1984 when 300,000 citizens demanded direct democratic elections following two decades of military rule.

Catedral da Sé

Dominating the Praça da Sé is the Catedral da Sé (Praça da Sé, tel. 11/3107-6832, 8 a.m.–7 p.m. Mon.–Fri., 8 a.m.–5 p.m. Sat., 8 a.m.–6 p.m. Sun., free, crypt R$5). The city’s main cathedral, this imposing mid-20th-century neo-Gothic building is large enough to hold 8,000 people. Architecturally, the church is not very alluring. However, the sculpted columns inside are unusual in that, along with the usual saints and angels, they feature tropical elements such as coffee beans, exotic fruits, toucans, and armadillos.

Edifício Sé

Directly across from the cathedral, at the far side of the praça, the magnificently brooding art deco Edifício Sé (Praça da Sé 111, tel. 11/3321-4400, 9 a.m.–9 p.m. Tues.–Sun., free) dates from the 1930s and serves as the São Paulo headquarters of Brazil’s federal bank, the Caixa Econômica Federal. The grandiose, marble-lined main floor and mezzanine have been renovated into a cultural center with interesting temporary exhibits. It’s really worthwhile to check out the bank’s offices and coffers. The wooden office furniture—gorgeously streamlined and made in Brazil—will delight design aficionados. Solar da Marquesa dos Sant os Just around the corner from the Edifício Sé is the pretty pink Solar da Marquesa dos Santos (Rua Roberto Simonsen 136, tel. 11/3241-6047, 9 a.m.–5 p.m. Tues.–Sun., free). São Paulo’s oldest residential dwelling, this 18th-century mansion’s former occupants included the Marquesa de Santos, who was the most famous mistress of Emperor Dom Pedro II. Today, it houses a small museum with temporary art exhibits devoted to different aspects of the city.

Páteo do Colégio

Around the corner from Rua Roberto Simonsen, you’ll find the Páteo do Colégio (Praça Páteo do Colégio 2, tel. 11/3105-6899, 9 a.m.–5 p.m. Tues.–Sun., R$5). This whitewashed Portuguese colonial edifice is actually a replica of the original 16th-century Jesuit college that was the first building in São Paulo. Founded by José de Anchieta and Manuel da Nóbrega, two priests who were bent on catechizing the region’s indigenous population, the college’s construction marked the beginning of the city’s history.

In the garden, where there is a pleasant café, you can see one of the college’s original walls, fashioned out of clay, leaves, and cattle blood. Part of the Páteo do Colégio, the small and rather modest Museu Padre Anchieta contains a few relics—such as the original 16th-century granite baptismal font—and documents that recount the history of São Paulo’s early years.

Mosteiro de São Bento and Vicinity

Continuing along Rua Boa Vista from the Páteo do Colégio brings you to Largo de São Bento. Amid a cluster of high-rise financial buildings is the Mosteiro de São Bento (Largo de São Bento, tel. 11/3328-8799, 6 a.m.–6 p.m. Mon.–Wed. and Fri., 6–8 a.m. and noon–6 p.m. Thurs., 6 a.m.–noon and 4–6 p.m. Sat.–Sun., free). Though it dates back over 400 years, the Benedictine monastery has received numerous facelifts over the centuries. Its basilica was built in 1912. Compared with the sober facade, the interior is more ornate. An interestingly subversive pagan touch is the painting of a red sun (representing God) with beams radiating the 12 signs of the zodiac. Most of the monastery is off-limits to visitors since its quarters are home to the Benedictine monks, who not only sing divinely (Gregorian chants are performed at 7 a.m. Mon.–Fri., 6 a.m. Sat., and 10 a.m. Sun.) but also bake well: Try the pão de mandioquinha (a type of sweet-potato bread) and the bolo Santa Ecolástica, a cake made with apples and walnuts, which are sold on the premises.

Near the monastery is a trio of more modern but equally striking landmarks. Built in 1901 to house the Banco do Brasil’s city headquarters, the Centro Cultural Banco do Brasil (CCBB) (Rua Álvares Penteado 112, tel. 11/3113-3651, 10 a.m.–9 p.m. Tues.–Sun.) is an opulent beaux arts building decked out with mosaic murals and crystal chandeliers that hosts a wide variety of cultural and artistic events. Close by, the Prédio do Banespa (Rua João Bricola 24, tel. 11/3249-7180, 10 a.m.–3 p.m. Mon.–Fri.) was São Paulo’s answer to the New York’s Empire State Building. Inaugurated in 1947, this grand skyscraper—headquarters of the Banespa bank—remains one of Sampa’s tallest buildings. From the panoramic deck on the 35th floor you are treated to impressive views of the city. Prior to the Banespa building, Sampa’s tallest building was the elegant Edifício Martinelli (Rua Libero Badaró 504), completed in 1929.

Viaduto do Chá

Going left down Rua Libero Badaró from the Edifício Martinelli brings you to the Vale do Anhangabaú, a narrow valley festooned with fountains and swaying palms and straddled by the Viaduto do Chá. Designed by 19th-century French architect Jules Martin, the Viaduto do Chá was the first of São Paulo’s many overhead passes. Its original purpose was to facilitate transport among the coffee plantations that occupied the valley. In more recent times, viaducts have mushroomed throughout the city in an attempt to ease Sampa’s crazy traffic flow.

From the Viaduto do Chá, you can get a sense of Sampa’s intense activity as well as a great view of two of the city’s most prestigious buildings. Inaugurated in 1939, the Palácio Anhangabaú (Viaduto do Chá 15) functions as São Paulo’s city hall. The shrubbery sprouting from the rooftop is actually a garden featuring over 400 native plants, among them coffee bushes, sugarcane, and even a mango tree.

More dazzling is the Teatro Municipal (Praça Ramos de Azevedo, tel. 11/3397-0300). Built at the turn of the 20th century at the behest of São Paulo’s coffee aristocracy, the theater reflects the opulence of the era (not to mention the art nouveau style of Paris’s Opéra Garnier). Venetian mosaics, Florentine sculptures, Italian marble, gold-leaf fixtures, and a chandelier with 7,000 crystals from Belgium are a few of the splendid trappings on display. You can take a free guided tour (10:15 a.m., 1 p.m., and 6 p.m. Mon.–Fri., 10 a.m. Sat.).

Largo de São Francisco

Returning to Rua Libero Badaró from the viaduto and continuing west, a short walk will bring you to the Largo de São Francisco. Crowning this square is one of São Paulo’s oldest churches, the Igreja das Chagas do Seráphico Pai São Francisco (tel. 11/3105-8791, 7 a.m.–5 p.m. Mon.–Fri.). It is one of the city’s finest examples of baroque architecture; construction began in 1676 and lasted for well over a century. The well-preserved interior features plenty of gold-leaf paneling, which adds shimmers of light to this otherwise dimly lit church. Also on the Largo is São Paulo’s highly reputed Faculade de Direito (Law Faculty) and the Igreja de São Francisco de Assis (tel. 11/3291-2400, 7:30 a.m.–7:30 p.m. Mon.–Sun.). Though it has suffered many alterations over the centuries, this church retains its original adobe walls from the 17th century.

Mercado Municipal

Within easy walking distance from Páteo do Colégio and the São Bento Metrô stop is São Paulo’s Mercado Municipal (Rua da Cantareira 306, tel. 11/3313-1326, 6 a.m.–6 p.m. Tues.–Sat., 6 a.m.–4 p.m. Sun.–Mon.), known affectionately by Paulistanos as the “Mercadão” (Big Market). Built in 1932, this vast neoclassical-style food hall featuring stained-glass windows with images of agricultural activities is a major mecca for the city’s restaurateurs and foodies. Each day, over 1,000 tons of fresh produce and delicacies imported from all over Brazil and the world are purchased from its 300 stalls. If you don’t feel like food shopping, simply feasting your eyes, nose, and taste buds on the variety of colors, aromas, and flavors is satisfying.

Should all the goods on display incite hunger pangs, head to the Hocca Bar (Rua G, Box 7), where you’ll have to line up in order to savor the pastéis de bacalhau (deep-fried pastries filled with salted cod) that have been a favorite snack since 1952. Other traditional snacks can be found at the market’s bars and lanchonetes, and at the recently renovated mezzanine, where a handful of restaurants offer a refreshing new slant on the food court concept.

Praça da República

At the tail end of the 19th century, Praça da República was hardly very republican—instead it was a posh downtown square around which São Paulo’s coffee barons built lavish city dwellings. However, as commerce—and its attendant trappings of noise, traffic, and riffraff—swept the city’s center, the barons decamped to a new and more bucolic neighborhood that came to be known as Higienópolis. Their former downtown mansions were quickly (and lamentably) destroyed, giving way to modernist buildings, some of them still quite striking, others sadly run-down. Today, Praça da República is a vibrant but somewhat forsaken square in need of a good renovation. On Sundays, it is the site of a colorful crafts and antiques market.

Two of the standout modernist buildings off of Praça da República have become Paulistano icons. Constructed between 1956 and 1965, Edifício Itália (Av. Ipiranga 344, tel. 11/2189-2929) was built with the mission of surpassing the reigning Banespa building in height. And indeed, for a long time, it proudly held the title as tallest building not only in town but in all of Latin America. Today, it is still top-ranked among the city’s skyscrapers. To take in the glorious view, ride the elevator up to the swank Terraço Itália restaurant, on the 42nd floor. If you don’t want to splurge for a mediocre meal or pay a cover charge at the bar, visits are free 3–4 p.m. weekdays. Quite remarkable from the outside is the Edifício Copan (Av. Ipiranga 200), a curling S-shaped building that could only have been dreamed up by Oscar Niemeyer. The building is as famous as a living space as it is for its design—boasting over 1,160 apartments and close to 6,000 residents, rare is the Paulistano who hasn’t known someone who has lived here at some point in time.

Excerpted from the Third Edition of Moon Brazil.