No Spanish-colonial town in Cuba is quite as beguiling as UNESCO-listed Trinidad, whose pastel-hued, terra cotta–roofed buildings lie in the verdant foothills of the Escambray Mountains. Cowboys from the surrounding countryside regularly roam on horseback through the cobblestone streets, past churches and well-preserved colonial mansions financed by the booming sugar cane industry (and slave trade) in the early to mid-1800s. Beyond the neo-Baroque monuments fronting Plaza Mayor, Trinidad’s beating heart, local residents dance to salsa and son cubano music into the early morning hours. The merrymaking reaches its peak during the annual Fiestas Sanjuaneras, a four-day celebration held around the last weekend of June: expect rodeos, traditional games, and an eye-popping parade of masked revelers and floats that nod to the Afro-Cuban roots of much of Trinidad’s populace.
Late afternoon at picturesque Plaza Mayor, the main square in Trinidad.