Florianopolis or Sao Paulo?

Florianopolis is a beach destination first, and few cities offer this much variety. The north shore has warm, sheltered bays, Mole, Joaquina and Campeche face the open Atlantic with real surf, and wild coves like Lagoinha do Leste can only be reached on foot or by boat.

Sao Paulo has no beach of its own. Santos and Guarujá lie at the bottom of the Serra do Mar, an hour or more away, with warm water but city sand, and the lovely coves of Ilhabela and Ubatuba need a weekend. If you want to swim every day, only the island works.

Sao Paulo is one of the great eating cities of the Americas, and the gap here is wide. Immigration gave it Japanese food in Liberdade, Italian cantinas in Bixiga and Lebanese cooking everywhere, and the ambitious restaurants of Jardins and Pinheiros sit alongside cheap padarias and botecos.

Florianopolis does one thing well, and that is seafood. Oysters by the water at Ribeirao da Ilha and Santo Antonio de Lisboa and a long sequencia de camarao are worth having, but after a week the beach menus start to repeat themselves.

Sao Paulo has far more to see, though its heritage is mostly modern. There is MASP on Avenida Paulista, Brazilian art at the Pinacoteca, the Museu da Língua Portuguesa in Luz station, and buildings by Niemeyer and Lina Bo Bardi. The sights are spread out, so expect to travel between them.

Florianopolis has charm rather than depth. The Hercilio Luz bridge, Praca XV with the Palacio Cruz e Sousa, the Azorean villages and the old bay fortresses make a pleasant day or two between beaches.

Sao Paulo goes out all year and all night. It runs from pavement botecos in Vila Madalena to the grittier bars of Baixo Augusta and electronic clubs that stay open until morning, and it has one of Latin America's largest LGBTQ+ scenes.

Florianopolis can only compete in high summer, when the beach clubs of Jurere Internacional and the bars around Lagoa da Conceicao fill up. In winter the island's nights shrink to a few bars, so the time of year matters far more there.

On the island, nature starts right outside the door. There are Atlantic forest trails to Lagoinha do Leste, the path along the Costa da Lagoa that only walkers and boats use, kitesurfing on the lagoon, sandboarding on the Joaquina dunes and whales off the southern coast.

In Sao Paulo, Ibirapuera Park is the green escape. For real landscape you have to go to the Serra do Mar or Campos do Jordão, and traffic eats into the day.

Neither city is a great base for excursions, and the outings are different in kind. From Florianopolis you follow the coast or head inland to German heritage: the surf towns of Garopaba and Praia do Rosa, the high-rises of Balneario Camboriu, and half-timbered Blumenau and Pomerode.

From Sao Paulo the choices are small towns and the port: Santos with its old coffee exchange, the craft market at Embu das Artes and the wineries of São Roque. Getting out through the traffic is the main hurdle, so start early.

Florianopolis has the edge for a family beach trip. Canasvieiras, Jurere and Daniela have shallow, calm water, there is sandboarding for older children, and Beto Carrero World is about an hour and a half north. Beyond the sand there is little aimed at children, and summer traffic between beaches tests everyone's patience.

Sao Paulo has more indoor attractions, such as the Catavento science museum, the zoo with its safari and the aquarium. Crowds, long drives and the need for care in the centre make it harder going with small children.

Neither city is easy to get around, but Sao Paulo is less awkward. Its clean metro links Paulista, Liberdade, Luz and Pinheiros, and ride-hailing fills the gaps, even though the network is small for a city this size and traffic is heavy.

Florianopolis has no metro, and its buses run through hub terminals, so a hire car or ride-hailing is close to essential. Summer jams on the narrow island roads are severe. Staying near the beaches you care about matters more here than choosing a district does in Sao Paulo.

Sao Paulo is Brazil's place to shop. It has designer labels on Rua Oscar Freire, lavish malls, the wholesale chaos of Rua 25 de Março and independent design studios in Pinheiros and Vila Madalena.

Florianopolis covers the basics with malls and surf and swimwear boutiques. Its one real souvenir is renda de bilro, the bobbin lace made in the Azorean villages.

Overall costs are much the same, but you pay more for different things. In Florianopolis the expense is summer accommodation, especially around New Year and Carnival and in Jurere Internacional. For the rest of the year, rooms are far cheaper.

In Sao Paulo, everyday life is cheap: set lunches, padaria coffee and metro fares, and many museums have free days. The stylish hotels and celebrated restaurants of Jardins, though, cost close to what they would in Southern Europe.

Sao Paulo has a full programme on stage. The state symphony plays at Sala São Paulo, the Theatro Municipal stages opera and ballet, musicals run in Portuguese, and bars host samba, choro and jazz. The SESC centres add low-cost concerts and dance.

Florianopolis has the Teatro Alvaro de Carvalho, the Centro Integrado de Cultura and acoustic sets in the bars of Lagoa. That is enough for an evening out, but not a reason to come.

For rest, the island is the better choice, at least outside high season, when the southern villages and quiet corners of Lagoa slow right down. Yoga studios cater to the surf crowd, and the hot springs of Santo Amaro da Imperatriz are less than an hour inland.

Sao Paulo is built for work and appetite. It offers upmarket day spas and Japanese-style relaxation spots, and its calmest moments are a Sunday on car-free Avenida Paulista or an afternoon in Ibirapuera.