Havana

The colonial core, all cracked plazas and balconies dripping laundry, dense with tourists but still alive with real life.

Best for culture · photogenic

Leafy, mid-century, and more residential — think Art Deco towers, the Malecón at sunset, and university energy.

Best for local · nightlife

Wide avenues, embassies, and the city's better private restaurants tucked into old mansions.

Best for foodie · romantic