Chile’s underrated capital of Santiago  offers fine hotels and restaurants, plus a surrounding landscape where (at some times of the year) it’s possible to ski in the morning and surf in the afternoon. Wine-oriented visitors can almost simultaneously enjoy the port city of Valparaíso  (a UNESCO World Heritage Site) and its neighboring beach resort Viña del Mar , the ski centers of Portillo  and Valle Nevado , and rafting on the Río Maipo. Complex logistics make a rental car desirable, if not quite imperative, for winery visits.
Depart midmorning for Viña Concha y Toro , Chile’s largest winery, in the suburb of Pirque. After tour and tasting, drive up the Cajón del Maipo  for lunch at San Alfonso , followed by white-water rafting down the Río Maipo. Alternatively, hike to a glacier at Monumento Natural El Morado , with a late afternoon return to Santiago.
Leave in the early morning, by rental car, for the Aconcagua valley . Plan on tours and tasting at Viña San Esteban (Los Andes ) and/or Viña Errázuriz (San Felipe ), continuing to the Pacific coast for Maitencillo’s luxury Marbella Resort  or other more economical accommodations. In wintertime, stay in Los Andes for a day’s skiing at Portillo .
Start a leisurely day at Maitencillo , with a midday excursion to Zapallar  (take binoculars to view the Humboldt penguins at nearby Monumento Natural Isla Cachagua ). A longer and more strenuous alternative could be an excursion to Parque Nacional La Campana , climbing its namesake peak for Andes-to-the-Pacific panoramas.
Take an almost equally leisurely drive south through Viña del Mar , Chile’s traditional summer vacation destination, to Valparaíso ; in winter, come directly from Los Andes to Viña and Valparaíso . Take an afternoon to explore the historic hills and backstreets of Chile’s main port, a UNESCO World Heritage Site that includes Neruda’s La Sebastiana  residence.
Departure midmorning for the Casablanca valley, southeast of Valparaíso , home to Chile’s finest white wines. Lunch at a winery restaurant such as Viña Indómita or House of Morandé before a late afternoon return to Valparaíso . Alternatively, stay at Viña Matetic’s secluded neocolonial guesthouse.
Leave early for Neruda’s Isla Negra  home, now a museum. It’s a fairly slow drive by paved back roads or a longer one by four-lane freeway to the Colchagua valley wine district. Look for accommodations in San Fernando , the gateway to Colchagua, or Santa Cruz ; if it’s not too late, take the day’s last tour at Viña Montes to enjoy the sunset over the valley.
Plan on a full day for Colchagua valley wineries, with a possible extension to the surfing capital of Pichilemu .
Sightsee for a full day in Santiago , with options such as the Museo Chileno de Arte Precolombino , including lunch at the Mercado Central  or in Barrio Bellavista . Depart in the evening from Aeropuerto Internacional Arturo Merino Benítez.