Santiago de Cuba, Cuba

Santiago de Cuba is the country's second-largest city and the capital of the southeastern province of the same name. It has been important throughout Cuba’s history—it’s actually older than Havana, albeit by only a month, having been founded on July 25, 1515, while the future capital followed on August 25. Its modern-day relevance, however, was cemented when Fidel Castro stood on Santiago's City Hall balcony on January 1, 1959, to proclaim the triumph of the Cuban Revolution. Santiago is also considered the cradle of the conflict: The famed (and failed) assault on the Moncada Barracks touched off the uprising in earnest. Today, many travelers make their way to Santiago to learn about that part of Cuba’s past, as well as to visit the graves of some of its most famous leaders, including Fidel Castro himself. His ashes are interred in the city's Santa Ifigenia Cemetery alongside the so-called father of Cuban independence, José Martí. Revolutionary history isn't the only reason to check out Santiago, however. There are UNESCO-inscribed sites, fascinating museums, popular venues for live music and—perhaps surprising to some—very good food.