São Paulo, the largest city in Brazil, is a cosmopolitan hub that boasts a dynamic blend of cultures, art, and cuisine. With a dizzying array of activities to choose from, it can be overwhelming for visitors to decide where to start. In this journey, we will try to help the traveler achieve an historic and also spatial understanding of how the city developed from a small village in the 16th century, to the largest metropolitan area of the southern hemisphere.

Day 1

Centro: From the city's founding grounds to latin music at a cozy cabaret

Start your day at the historic Padaria Santa Tereza, the oldest bakery in São Paulo, serving locals since 1872. I wouldn't miss their hearty version of "Bauru", a São Paulo traditional ham, cheese and tomato sandwich that is Brazil's response to a BLT. As you enjoy your breakfast on the 19th century mezzanine, take in the view of the iconic Catedral da Sé and feel the energy of the bustling city waking up around you.

Step outside and explore the surrounding area, starting with Catedral da Sé, a towering neo-gothic temple that is one of the city's most iconic landmarks. Built in 1913, showcasing the defining design elements of Gothic architecture, Catedral da Sé features sculptures of Brazilian animals such as armadillos, toucans, lizards, herons and plants such as the passion fruit, coffee and jabuticaba. It seems like they are playing hide and seek looking down on us humans from the column capitals.

Take a five-minute walk and land on Pateo do Collegio, the birthplace of the city founded by Jesuit priests in 1554 in a mission to convert native Brazilians to christianity. Chief Tibiriça was the first of them and his baptism is considered the founding act of the city. Whenever you are ready for more history take a stroll to Mosteiro São Bento. A great idea is to check the monastery's schedule as it is known as both a place of faith, art and music but also every other weekend is a place of feast for all senses as the dedicated Benedictine monks host a luxurious brunch featuring a different local chef in each event. The six-hour experience starts with a Gregorian chant mass, then a bountiful brunch followed by a tour through the museum and sumptuous rooms of the historic building. The brunch (R$357 per person) is usually sold out one month in advance, so plan ahead to enjoy the most of this experience.

Still in the city center, another mandatory stop is Pinacoteca do Estado de São Paulo, the city's oldest museum, and its impressive collection of Brazilian art from the 19th century to the present day. Don't miss the chance of being in the presence of iconic paintings from the Brazilian Anthropophagic Artistic Movement such as ‘Mestiço’ by Cândido Portinari, ‘Antropofagia’ by Tarsila do Amaral and ‘Bananal’ by Lasar Segall. Continue your journey at Pina Contemporânea, a brand new building with spacious galleries, a library and a majestic hall showcasing big names of contemporary Brazilian art, such as Tunga, Carmela Gross, Adriana Varejão and Emanuel Araújo. With this new addition, Pinacoteca has become the second largest museum of Latin America.

Not too far from Pinacoteca is Bom Retiro. This diverse neighborhood is considered the 25th coolest in the world by Time Out Magazine. Bom Retiro, located in the heart of São Paulo, is a vibrant and diverse neighborhood that represents the multiculturalism of Brazil. Known for its fashion district and busy street markets, Bom Retiro is home to a diverse population that includes Jewish, Korean, and Lebanese immigrant communities, and more recently, attracted Bolivian, Paraguayan and African people who opened shops, bakeries and restaurants. A must-try gastronomic experience is the Korean barbecue as there are dozens of restaurants offering the Asian version of a carnivore feast. Our favorite spot is Cho Sun Gal Bi, where the friendly staff helps you prepare your own barbecue on a charcoal grill in the center of the table and keeps bringing spicy side dishes such as kimchi, tofu, and rice to your table until there's no more room for dessert.

Another lunch option in São Paulo City Center is located in the iconic COPAN Building: the trendy restaurant Cuia by Chef Bel Coelho where you can shuffle books at Megafauna bookstore and take in the stunning views of one of architect Oscar Niemeyer's most audacious designs. Indulge in a cup of locally roasted coffee at Floresta, a specialty coffee shop known for its quality beans. But don't come expecting obnoxious baristas and latte art. This family-owned café has been run by Regina and her uncles for 45 years and they never bothered to update the facade or hire hipster baristas. Thank goodness! Just get your strong coffee, a cheese roll, get down to business and move fast.

For some retail therapy, stop by the Cassia Cipriano hat shop and Korova for the coolest t-shirts you can possibly find featuring São Paulo landmarks, then cross the beautiful Avenida São Luiz towards Galeria Metropole. A modernist building that used to be packed with travel agencies and walk through its terraced corridors to see several new stores owned by young local fashion and home designers. The welcoming gallery still blends some old school businesses, botecos where paulistanos enjoy watching soccer matches after work, cafés, wine shops and vintage clothing boutiques.

To take a breath from all the concrete, head to Parque Augusta, a favorite of the local LGBTQIAP young families to bring their toddlers and pets. You will be pleased to come across jolly groups of local beauties sunbathing and gathering for picnics.

One of our favorite post-pandemic new openings in the city center is Cineclube Cortina, built where there used to be a parking lot. This multicultural place has a movie theater that can be morphed into a dance floor in its basement and a restaurant and bar on the ground level. The signature drinks are created by the very talented Chula barmaid, from Argentina, and the food menu, crafted by chefs Daniela França Pinto and Fernanda Camargo, feature the fusion of cuisines that make São Paulo's restaurant scene one of the most diverse and exciting in the world.

Day 2

Paulista, Jardins and Ibirapuera

Start your day with a breathtaking view of the city from Mirante Sesc Paulista. Marvel at the modern architecture and feel the energy of the busy Avenida Paulista - where local workers, tourists, families and rioters meet and mix on their way to the many offices, stores, shopping malls and cultural centers.

To have a glimpse of the cultural significance of Paulista, start at Japan House, an art center dedicated to showcasing eminent contemporary Japanese artists, designers, and tech innovators. With its beautifully designed spaces and engaging programming, Japan House is a must-visit destination for anyone interested in exploring the fascinating world of Japanese culture and its influence in São Paulo.

Walk across the avenue to Itau Cultural and visit the Brasiliana Collection, one of the largest corporate collections in the world and the largest in South America, featuring the history of Brazilian Art and how the country was portrayed by French, Dutch and German artists in the three-century time-span of Portuguese colonization in Brazil. Continuing the art stroll, make a stop at MASP, to admire its bold architecture that stands out among the city's skyline. As impressive as its architecture, the MASP collection includes works by artists such as Rembrandt, Van Gogh, Picasso and Brazilian modernist and contemporary artists.

To conclude your art journey on Avenida Paulista, stop by IMS (Instituto Moreira Salles) for pictures on the rooftop and check out the photography exhibitions the museum offers the whole year. At the back of the lobby, you will find renowned restaurant Balaio, by charismatic chef Rodrigo Oliveira and his elevated yet innovative Brazilian cuisine.

Jardins, the upscale neighborhood offers shopping and dining options for all tastes, but a visit to Havaianas Oscar Freire is mandatory if you want to bring souvenirs back home. The stunning flagship store of this iconic Brazilian brand sells exclusive and customized flip-flops you won't find anywhere else.

For some sweet treats, visit Amma Chocolates, a boutique chocolatier famous for their beautiful chocolate bars made in Bahia with cacao from Bahia and flavored with ingredients from the Amazon.

Late in the afternoon is time to take a stroll at Ibirapuera, where thousands of locals get their workout done every day. This sprawling park, designed by Oscar Niemeyer, boasts a stunning array of natural beauty and cultural attractions. Visitors can wander through the serene gardens and wooded areas, taking in the sights and sounds of birds chirping and leaves rustling in the breeze. The park is also home to numerous art installations and museums, showcasing the rich cultural heritage of Brazil. From the striking Modernist architecture of the São Paulo Museum of Art to the thought-provoking exhibits at the Afro Brazil Museum, Ibirapuera Park offers a truly unique and enriching experience for travelers of all ages and interests. The park also offers eateries and dining options. One of our recent outings at the park included a late lunch at Selvagem, a beautifully decorated restaurant surrounded by gigantic trees and tropical plants. The cashew caipirinhas are among the best ones in the city along with their grilled octopus.

Day 3

Vila Madalena: Graffiti and heavy strokes of bohemia

Considered the 13th coolest neighborhood in the world for its many bars, restaurants, music venues and street art, Vila Madalena attracts many paulistanos, Brazilians and international tourists visiting São Paulo.

Start your day at the vibrant and ever changing Beco do Batman, a street filled with vibrant graffiti by renowned Brazilian street artists such as Kobra, Tupys and OsGemeos. The several streets that compose this alley are packed with laid back bars, galleries and shops selling vinyl records, jewelry and street fashion.

Stop at Boteco do Edy and try one sip (yes, one is enough!) of Cachaça Jambu before indulging in a delicious lunch at Lobozó or shopping for ingredients from Brazil's six major ecosystems at Mercado de Pinheiros, where seafood lovers can indulge in oysters and ceviche at Comedoria Gonzales by Bolivian-Brazilian chef Checho Gonzales.

After lunch, indulge in some house-made gelato at Pinguina, and then head to Galeria Millan, Instituto Tomie Ohtake or MUBE to explore contemporary art. Later in the afternoon take a walk on Rua Mateus Grou for Brazilian modern jewelry and trendy fashion shops, followed by a visit to Feira na Rosenbaum. One of our favorite shopping experiences is offered at Calma São Paulo, by designer Kelly Kim and her gender-neutral tropical kimonos that, thanks to their flowy shapes, make people in all body sizes look gorgeous.

For dinner, try Preto Cozinha, which offers an authentic taste of Brazilian cuisine focusing on seafood. End the night with some Brazilian jazz at Julinho's Club or samba at Bar Samba, and then dance the night away to forró at Bar do Baixo.

By the end of your three-day tour, you will probably feel that you’ve missed something, as São Paulo is such an effervescent and vibrant city and it is impossible even for locals to stay up-to-date with the city's constant transformation. So yes, you will definitely feel like coming back.

Content contributed by Janaina Hvass and Flavia Liz di Paolo from Flavia Liz Personal Tour Specialist. Image credits: Catedral da Sé photo by Nathalia Segato on Unsplash. Pinacoteca photo by Rodrigo Soldon on Flickr. COPAN photo by Pablo Trincado on Flickr. Paulista photo by Bianca Monteiro on Unsplash. MASP photo by mari_aquino on Flickr. Ibirapuera Park photo by Rosa Menkman on Flickr. Beco do Batman photo by ckturistando on Unsplash. Mercado de Pinheiros photo by jACK TWO on Flickr. MUBE photo by paulisson miura from Cuiabá, Brasil (CC BY 2.0) via Wikimedia Commons.