The chaotic counterweight to Santiago’s orderly vibe, port city Valparaiso is a colourful mess of winding streets, ramshackle houses and sweeping coastal views. A World Heritage City, Valparaiso’s decidedly bohemian vibe has long inspired the poets, painters and writers who called the city home, and today it continues to draw artists from across the globe to adorn its crumbling walls. Visitors can enjoy some of the best street art in Latin America — the city took inspiration from Mexico’s growing muralism movement in the 1940s — before heading down the wharfs for some freshly-caught seafood and fish empanadas.