1. Trinidad, Cuba
Founded in 1514 by Diego Velaquez, Trinidad was declared a UNESCO World Heritage site in 1988. During the 17th and 18th centuries, the city was a wealthy slave-trading centre and hub of sugar production and its wealthy landowners and merchants erected fine homes and mansions. The cobblestone streets lined with pastel coloured houses have barely changed since the colonial era; Trinidad feels like an attraction that time has passed by. Unlike most cities in Cuba, Trinidad sits on a hill and is cooled by near-constant breezes.