Paraty or Sao Paulo?

Paraty is the beach destination of the two, though not because of its own town beaches, which are shallow and murky. The real pleasure is a boat trip to the forest-backed coves around the islands of the bay. Trindade, about forty minutes away, adds open-sea beaches and the clear rock pool at Cachadaço.

Sao Paulo sits inland on its plateau. Its nearest sand, at Santos and Guarujá, is an hour or more away, and those beaches are wide and urban rather than pretty. The lovely north coast around Ubatuba needs a whole weekend, and the weekend traffic heading down to the sea makes even that a slog.

Sao Paulo is one of the main reasons to visit Brazil for food: the Japanese counters of Liberdade, Bixiga's pizza and cantinas, Lebanese and Syrian cooking, feijoada days, the Mercado Municipal and some of South America's most ambitious kitchens in Jardins and Pinheiros.

Paraty's table is narrower and coastal, with grilled fish, shrimp and the blue-green azul marinho stew served in candlelit townhouses. Its real speciality is cachaça, tasted at small distilleries in the hills, but there are no markets or street food to explore.

The two offer heritage of opposite kinds. Paraty is a single, intact UNESCO-listed ensemble of whitewashed colonial houses and baroque churches such as Santa Rita, built on the gold trade, and its charm lies in the whole streetscape rather than individual sights, which are covered in a day.

Sao Paulo has much more to visit, though almost all of it is modern: MASP's glass easels, Brazilian art at the Pinacoteca, the language museum in Luz station and the architecture of Niemeyer and Lina Bo Bardi. Colonial buildings are scarce and the sights are spread far apart.

Sao Paulo goes out all night, moving from pavement botecos to cocktail bars to clubs after 2am, with Vila Madalena, Baixo Augusta, Pinheiros and República each drawing a different crowd, internationally known electronic venues and one of Latin America's largest LGBTQ+ scenes.

Paraty's evenings are a long dinner and a drink with a guitarist playing. The centre stays lively late only at weekends and in high season, Trindade's beach parties suit backpackers, and there are no real clubs.

Paraty is surrounded by its landscape: Atlantic rainforest rising into Serra da Bocaina, the old Gold Trail, waterfalls and swimming holes, a bay of green islands for kayaking and snorkelling, and the fjord-like Saco do Mamanguá reached by boat.

In Sao Paulo, nature mostly means Ibirapuera Park and the Cantareira hills on the edge of the city. The Serra do Mar trails and Paranapiacaba are an hour or two out, and traffic turns most outdoor plans into early starts or weekends away.

Sao Paulo gives you a longer, if modest, list of outings: historic Santos and its coffee exchange, the craft market at Embu das Artes, wineries at São Roque and interior towns such as Itu and Holambra, all best done on a weekday to dodge traffic.

Paraty is more somewhere to stay put. Trindade is the easy trip, while pottery studios in Cunha and the beaches of Ubatuba each take a longer drive, and Ilha Grande really deserves its own night or two.

Sao Paulo has more organised for children: the hands-on Catavento science museum, a zoo with a drive-through safari, a large aquarium, Ibirapuera's playgrounds and theme parks near Vinhedo. The price is long car journeys, crowded pavements and staying alert in the centre.

Paraty's appeal for children is simpler and outdoors, with swimming stops on calm island beaches, the rock pools at Trindade and the waterfall slide. There is nothing built for them, and the old town's big uneven stones are hard work with a pushchair.

Both are awkward in their own way. Paraty's car-free centre crosses in ten minutes on slow, rounded stones, but the beaches, waterfalls and distilleries need a boat, bus, taxi or tour.

Sao Paulo has a clean, easy metro that is simply too small for the city, so ride-hailing fills the gaps through heavy traffic. Districts like Jardins and Vila Madalena walk well on their own, but walking between sights rarely works.

Sao Paulo is Brazil's shopping capital, from Brazilian labels and swimwear on Rua Oscar Freire and lavish malls to the wholesale chaos of Rua 25 de Março, the garment district of Bom Retiro and design studios in Pinheiros.

Paraty offers a pleasant evening browse instead: galleries, linen and jewellery boutiques in colonial shopfronts, and souvenirs such as hand-labelled cachaça, indigenous basketry and painted wooden boats, with no fashion shopping at all.

For visitors from Europe or North America both feel moderately priced, and the difference lies in where the money goes. Sao Paulo's everyday life is cheap, with set lunches, padaria coffee, botecos, metro rides and free museum days, while its smart hotels and acclaimed restaurants approach Southern European prices.

Paraty charges resort prices for old-town pousadas and its better restaurants, especially on long weekends and at festival time, but shared schooner trips, kiosks and simple fish places are good value, and staying just outside the centre saves noticeably.

Sao Paulo has a full calendar: the state symphony at Sala São Paulo, opera and ballet at the Theatro Municipal, Portuguese-language musicals, samba circles, choro and jazz clubs, low-cost SESC programmes and the all-night Virada Cultural.

In Paraty, music is samba and bossa nova played over dinner, with puppet theatre and festival street performance now and then. Its famous literary festival is about books and talks rather than performance.

Neither has a bathing tradition, but Paraty is far easier to unwind in. A quiet car-free old town out of season, garden pousadas with hammocks and pools, and forest or bayside retreats make it a place to switch off.

Sao Paulo offers polished day spas in Jardins and Itaim, salons and a few Japanese-style relaxation spots, yet the city's pace works against rest; a Sunday on car-free Paulista or under Ibirapuera's trees is the nearest it comes.