Santiago, Chile’s thriving capital, unites the best of modern city life with a prime geographical position between the Andes mountains and the Pacific Ocean. Mixed into the melting pot of colonial architecture and Latino flair, Santiago highlights such as Bellavista, thronged with street art and chic bars; San Cristobal Hill (Cerro San Cristobal); Plaza de Armas; and Mercado Central (Central Market) top the list for most travelers—and are easy to tick off, plus more, on a hop-on hop-off sightseeing tour. Just 1.5 hours west of Santiago, Valparaiso is a UNESCO World Heritage port city with a historic quarter full of winding alleys; colorful houses; and 19th-century funiculars (cable railways), which take you up Concepción and Alegre hills. Neighboring Viña del Mar, or the Garden City, boasts pretty parks and historic architecture—visit both in one day on a day trip from Santiago. And no visit to Santiago is complete without a jaunt into its valleys. Maipo Valley, or El Cajon del Maipo, is a beautiful natural spot for camping, hiking, and a variety of sports. Just as impressive as the gorge is its array of famous wineries: the vineyards and cellars of Concha y Toro Winery, Santa Rita Winery, and Undurraga Winery all offer wine-tasting tours.