The sloping streets of gritty-arty Valparaíso, a UNESCO World Heritage city 75 miles west of Santiago, are best traversed by a network of a dozen-plus funicular elevators, or ascensores, dating to the late nineteenth century. In minutes and for less than $1, the rickety ascensores bounce riders from sea level to some of the 45 hilltop neighborhoods (called cerros), each a world of its own. (The one-way tickets are sold at station entrances; check ascensorevalparaiso.org for maps.) Base yourself at Cerro Alegre’s newly overhauled Palacio Astoreca (from $230; hotelpalacioastoreca.com), a 23-room mansion now kitted out with a slate-lined spa and heated pool. From here, you’ll be in the thick of Valpo’s dining-and-nightlife scene, not to mention directly above El Bullí–trained Spanish chef Sergio Barroso’s restaurant inside the Palacio, Alegre (Calle Montalegre 149; 56-32-327-7700), where seasonal menus include plates like spicy merkén-crusted conger eel. Stroll down the promenade to take in the work of Porteño painter Thomas Somerscales at the renovated Museo de Bellas Artes in the Art Nouveau Palacio Baburizza (Paseo Yugoeslavo 166; 56-32-225-2332), and later, explore the buzzing boutiques and galleries of nearby Cerro Concepción. For handwoven rugs, clay cookware, and other artisanal souvenirs, Concepción’s Kipu (Paseo Gervasoni 408; 56-32-259-1149) is a must.
The thrill-o-meter: Minor buzz.