The place where you choose to live depends to a large extent on economic factors. After WW1 a lot of American artists and writers (Hemingway, Miller, Scott Fitzgerald, ...) went to live in Paris because the dollar exchange rate was favourable, and it was cheap for them to live there. When the economic circumstances changed, they left.
If I were rich, Manhattan’s Upper West Side would do very nicely for me. Somewhere like 70th St between Columbus and Central Park West. Nothing very grand, just a little apartment in some nice townhouse. Vargas Llosa used to have an apartment there. (Munoz Molina lives other side of park – no, thank you, too posh for me).
As I’m not likely to become rich, that’s out of the question.
Sarasota, Florida, might be nice. It has a theatre, an art centre, and an anual film festival. Too hot in summer, though.
San Diego, California, would be ok, but too expensive.
Then it’s southern Europe. Spain, perhaps.
San Sebastian. Beautiful place, great food, but too rainy and too expensive.
Barcelona. Great place, good food, very good bookshops – but too expensive, and too hot and sticky in summer.
Madrid. Good communications, good food, great museums, but it’s getting too noisy and it’s not cheap anymore.
Granada might be my favourite in Spain.
But I think I’d settle for Lisbon. It’s spectacularly beautiful, there is good food, there are some great museums, and it’s not as expensive as most southern European cities.
Somewhere near Rua Saraiva de Carvalho, or Rua Coelho da Rocha, where Pessoa lived at the end of his life. It’s a quiet part of the city, and it’s not far from the Prazeres cemetery: after all, it was going to be the city of my final destination...