Valparaiso is perhaps Chile’s most fascinating port town and the former residence of the legendary poet, Pablo Neruda. Awarded a UNESCO World Heritage status, Valparaiso is a wonderful mix of steep hillsides (with near-vertical funiculars) and cobblestoned streets fenced by colorful colonial buildings, reflecting the influx of the European immigrants during the 19th century. Visit the iconic La Sebastiana, the former eccentric mansion of Pablo Neruda, which has now been converted into a museum that offers a keen insight into the poet’s life (the breathtaking Pacific vistas are a bonus). Not just Neruda, but many poets, painters and philosophers were fascinated by Valparaiso’s unique charisma and drew much inspiration from the port town. Wander through the old streets with its bohemian vibes and enjoy the serene seaside views coupled with a fast-paced nightlife and an appealing underground street art scene, which is said to be one of the best in all of Latin America.