Ilhabela, Brazil

Ilhabela's ferry-dependent access creates a double-edged sword. The 15-minute ride from São Sebastião keeps mass tourism at bay, but also means grocery runs require planning when storms cancel boats. Between December and February, the population swells with Brazilian vacationers—expect packed beaches and higher short-term rental prices.

This isn't a place for urban conveniences. The cobblestone streets of Vila (downtown) flood during summer rains, and healthcare options are limited to basic clinics. But that isolation preserves Atlantic Forest trails and empty coves you'll share with toucans. Digital nomads thrive here with Starlink, but retirees need Portuguese to navigate bureaucracy.