Two countries, one bold week. This 7-day Brazil-and-Cuba itinerary stitches together São Paulo’s culture and coffee, Américo Brasiliense’s small-town warmth with nearby nature in Brotas, and Havana’s spellbinding history, music, and cuisine. You’ll taste pastel and mortadella sandwiches in São Paulo, sip sugarcane juice inland, then toast sunset on the Malecón in a 1950s convertible.

São Paulo is Latin America’s culinary laboratory, a city of museums, murals, and markets. Inland, São Paulo state softens into rolling farms and river-cut canyons perfect for rafting and waterfall hikes. Américo Brasiliense sits by Araraquara and within easy reach of Ribeirão Preto’s legendary chopp (draft beer) scene and Brotas’ adventure playground.

In Cuba, Havana’s Old Town is a living museum—baroque plazas, music from every doorway, and paladares crafting ropa vieja and rum-forward cocktails. Bring cash (USD or EUR), expect spotty internet, download offline maps, and savor the pace: Havana rewards flâneurs and night owls alike.

São Paulo

Brazil’s biggest city thrums with energy—concrete and green, graffiti and galleries. Start with Ibirapuera Park and Paulista Avenue, then zigzag into pinball-bright alleys in Vila Madalena’s Beco do Batman. São Paulo’s food scene is a world tour: Japanese in Liberdade, Syrian-Lebanese in Pari, Northeastern Brazilian in Pinheiros.

• Top sights: Ibirapuera Park, MASP (art museum), Beco do Batman street art, Mercado Municipal, Historic Center (Pátio do Colégio), Liberdade district.
• What to eat: mortadella sandwich and pastel de bacalhau at Mercado Municipal; modern Brazilian at Bar da Dona Onça; specialty coffee in Pinheiros.

Where to stay: Search stays on VRBO São Paulo or compare hotels on Hotels.com São Paulo. For flights into Brazil, check Trip.com flights or Kiwi.com.

Américo Brasiliense

A friendly town west of São Paulo city, Américo Brasiliense puts you close to classic São Paulo state experiences: cane fields, coffee, hearty countryside cooking, and neighboring cities with lively dining. It’s an easy springboard to Araraquara, Ribeirão Preto, and the waterfalls and rafting rivers around Brotas.

• Nearby highlights: Ribeirão Preto’s iconic Pinguim choperia; Brotas for rafting, zip-lines, and canyon hikes; Araraquara’s bakeries and sunny plazas.
• Good to know: Limited hotels in town—consider overnighting in Araraquara or Ribeirão Preto and day-tripping to Américo.

Where to stay: Try VRBO Américo Brasiliense or Hotels.com Américo Brasiliense. If options are scarce, look at Hotels.com Araraquara or Hotels.com Ribeirão Preto.

Havana

Havana is a mood—salsa echoing through 18th-century plazas, classic Chevrolets cruising the Malecón, and sunset light pooling on pastel facades. Old Havana (Habana Vieja) is dense with UNESCO-listed treasures and intimate paladares serving home-style Cuban cooking.

• Top sights: Plaza de la Catedral, Plaza Vieja, Castillo de la Real Fuerza, Museo de la Revolución, Paseo del Prado, Malecón, Fábrica de Arte Cubano (nightlife).
• Good to know: Bring cash (USD/EUR), as many cards don’t work; expect intermittent connectivity; taxis from HAV airport to Old Havana are typically USD 25–35.

Where to stay: Browse VRBO Havana or compare hotels on Hotels.com Havana. Two tried-and-true options: boutique Casa Vitrales (Old Havana charm) and classic Iberostar Parque Central (rooftop pool, central location).

Day 1: Land in São Paulo (Arrival Day)

Afternoon: Arrive at GRU or CGH and settle into your hotel in Jardins or Paulista for easy dining and transit. Shake off jet lag with a lap of Ibirapuera Park—Oscar Niemeyer’s pavilions gleam between lakes and jacarandas.

Evening: Start at Coffee Lab in Pinheiros for a Brazilian terroir flight—barista-led tastings spotlight Cerrado and Mogiana beans. Dinner at Bar da Dona Onça near Copan: order moqueca or oxtail with pirão; it’s a love letter to Brazilian comfort food. Cap the night with skyline views at Terraço Itália’s piano bar.

Day 2: São Paulo’s Icons, Street Art, and Market Eats

Morning: See the city’s greatest hits with a private guide: MASP’s floating gallery, Paulista Avenue, historic center, and Beco do Batman’s murals.

Book it on Viator: Amazing São Paulo overview in 4 or 5 hours with a private guide

Afternoon: Graze at Mercado Municipal: split the skyscraper-sized mortadella sandwich and the pastel de bacalhau (salt-cod turnover) at Hocca Bar, then juice from tropical fruits you’ve never met. Walk Liberdade’s lantern-lined streets for Japanese-Brazilian sweets and matcha soft-serve.

Evening: Dinner in Vila Madalena—try modern Northeastern fare at Fitó (sun-dried beef escondidinho; cashew-nut sweets). Hop between craft-beer bars along Rua Aspicuelta, or keep it coffee-forward at Sofá Café’s evening brew bar.

Optional add-on (6 hours): Visit a historic coffee farm 80 km from São Paulo for stories of Brazil’s coffee boom and a home-style lunch.

Book it on Viator: São Paulo Coffee Tour: Farm, Culture & Lunch Included – 6h

Day 3: São Paulo to Américo Brasiliense (via Araraquara/Ribeirão Preto)

Morning (travel): Depart São Paulo for the interior. Options: drive (~4 to 4.5 hours, BR-364/Anhanguera; tolls ~R$50), intercity bus to Araraquara (4.5–5 hours; ~R$120–160) then short taxi/Uber to Américo, or fly CGH/VCP to Ribeirão Preto (RAO) (~1 hour; from ~$60–140 one-way) and pick up a car for the ~1.5-hour drive. Search fares on Trip.com flights or Kiwi.com.

Afternoon: Check in around Araraquara or Ribeirão Preto, then visit Américo Brasiliense’s central square and Matriz São João Batista. Sip caldo de cana (fresh-pressed sugarcane juice) and try a pastel stuffed with carne or queijo at a local pastelaria.

Evening: In Ribeirão Preto, raise a chopp at Pinguim—an institution since the 1930s famed for frosty tulip glasses and German-Brazilian snacks (linguiça with pão francês, bolinho de bacalhau). For dinner, go rodízio-style at a churrascaria (picanha, fraldinha, grilled pineapple) or sample regional plates like tutu de feijão and torresmo at a mineira canteen.

Day 4: Adventure Day in Brotas (Waterfalls, Rafting, and Springs)

Morning: Drive ~1.5 hours to Brotas, São Paulo’s adventure capital. Tackle a guided rafting run on the Jacaré-Pepira River (Class II–III rapids) or opt for canyoning/zip-lines through forest canyons. Bring water shoes and a dry bag.

Afternoon: Lunch at Brotas Bar—raft-themed décor, crispy tilápia, mandioca fries, and house caipirinhas. Then cool off at Recanto das Cachoeiras for waterfall swims and short trails, or book a visit to Areia que Canta, an emerald spring whose sand “sings” underfoot.

Evening: Return to base. In Ribeirão Preto, sample local craft at Invicta’s taproom (IPA and wood-aged specialties) or sip a caipirinha made with cachaça from nearby sugarcane country. Early night—tomorrow is a big travel day.

Day 5: Brazil to Cuba — Havana Arrival

Morning (travel): Head back to São Paulo (or connect via RAO/VCP) for flights to Havana (HAV). Typical routes are via Panama City with Copa or Bogotá with Avianca; total travel time ~10–15 hours depending on connections. Compare options on Trip.com or Kiwi.com (one-way fares often ~$500–900).

Afternoon: Arrive in Havana and check into Old Havana. If you like boutique intimacy, Casa Vitrales has vintage tiles, balconies, and a gracious breakfast; for pools and centrality, Iberostar Parque Central is a classic choice.

Evening: Take a 1950s classic car along the Malecón at golden hour, looping past the Capitolio and Hotel Nacional. Dinner at San Cristóbal Paladar—where President Obama dined—serving ropa vieja, lobster, and guava-and-cheese desserts. Nightcap on La Guarida’s rooftop with a daiquirí.

Day 6: Old Havana’s Plazas, Museums, and Music

Morning: Breakfast at El Café (sourdough toasts, eggs, strong espresso). Wander Plaza de la Catedral, Plaza de Armas, and Plaza Vieja; peek into independent galleries along Calle Obispo and watch woodworkers at Plaza de Armas’ bookstalls.

Afternoon: Lunch at Doña Eutimia (reserve if possible) for ropa vieja or grilled octopus. Then the Museo de la Revolución in the former Presidential Palace lays out turbulent 20th-century history—finish with a stroll down Prado’s tree-lined promenade to the sea.

Evening: Fábrica de Arte Cubano (FAC) blends galleries, live bands, and dance floors inside a repurposed factory—arrive after 8 pm, bring cash for entry and drinks. Prefer classic vibes? Catch son and bolero sets at a casa de la música near Old Havana.

Day 7: Beach and Farewell Havana (Departure Day)

Morning: Quick escape to Playas del Este (Santa María del Mar) ~25 minutes by taxi—calm turquoise, chair rentals, and beachside mojitos. If you’d rather stay in town, tour the rum history at a tasting bar and pick up coffee and cigar souvenirs.

Afternoon: Last bites at El Chanchullero (tapas, cold beers, cheeky chalkboard slogans) or Habana 61 (seafood and citrusy mojo). Swing by Almacenes San José for crafts, then transfer to the airport for your afternoon departure.

Evening: In transit—scroll through photos of street murals, waterfalls, and candy-colored Buicks. Até logo, y hasta pronto.

Accommodation quick links:

• São Paulo stays: VRBO | Hotels.com
• Américo/Araraquara area: VRBO | Hotels.com
• Havana stays: VRBO | Hotels.com | Boutique: Casa Vitrales | Classic: Iberostar Parque Central

Transport booking: For all flights (Brazil domestic and Brazil–Cuba), compare on Trip.com and Kiwi.com.

In a week you’ll collect a surprising range of memories: São Paulo’s art and market flavors, inland Brazil’s rivers and small-town pace, and Havana’s luminous nights. It’s a compact itinerary with real texture—history, food, nature, and music—tailored for travelers who like contrast and momentum.