Libertador General Bernardo O'Higgins

The Colchagua Valley has become Chile's most prestigious red-wine destination, celebrated above all for Carmenère — a Bordeaux grape variety thought extinct after a 19th-century European blight, later found still growing, misidentified, in Chilean vineyards, and now the country's signature red. Around the wine town of Santa Cruz, a dense concentration of both historic and boutique estates — among them Casa Silva, Viu Manent, Montes and Lapostolle — offer cellar tours, tastings and destination restaurants set among the vines, with the Cordillera de la Costa hills providing a scenic backdrop. A narrow-gauge heritage train, the Tren del Vino, links several wineries for a relaxed, sociable way to taste without driving. Santa Cruz's excellent Museo de Colchagua, one of Chile's finest private museums, rounds out a visit with wide-ranging collections spanning pre-Columbian cultures, colonial history, horse-drawn carriages and even the capsule used in the 2010 rescue of the trapped Chilean miners. The valley rewards at least a full day, with the March–April harvest season an especially lively time to visit.

Pichilemu, on the O'Higgins coast, is Chile's best-known surf town and a magnet for wave-riders of every level. Its signature break, Punta de Lobos, a long, powerful left-hand point break beneath dramatic coastal cliffs, is ranked among the finest waves in the southern hemisphere and hosts international competitions, while the town's own beaches and several nearby breaks offer options for beginners and intermediates, with numerous surf schools and board rental shops. Beyond surfing, Pichilemu has a laid-back, youthful beach-town atmosphere, with a scenic clifftop walk, fresh seafood restaurants and a scattering of boutique hotels and hostels. The town's relative remoteness from Santiago (around three hours by road) has kept it less developed than Chile's more touristy beach resorts, part of its appeal for travellers seeking an authentic surf-town base rather than a polished resort.

Rancagua, the regional capital, is the ceremonial home of Chilean rodeo, a distinct sport from its North American counterpart, in which two huasos (Chilean cowboys) on horseback work together to pin a steer against padded boards in a crescent-shaped arena, all performed in traditional dress — the wide-brimmed chupalla hat, colourful manta poncho and ornate silver spurs. The city hosts the national rodeo championship each spring, a major cultural event blending competition with traditional food and the cueca, Chile's national dance — a courtship dance performed by a couple waving handkerchiefs in a circling, flirtatious pattern, danced socially between rodeo events rather than staged purely for spectators — and rodeo grounds (medialunas) can be found in towns throughout the region and country beyond the championship dates. Just outside Rancagua, the El Teniente mine ranks among the largest underground copper mines in the world, a reminder of mining's central role in the Chilean economy, though visits are generally limited to specialist tours. Nearby, the Rapel reservoir offers watersports, fishing and lakeside relaxation, a low-key complement to the wine and coastal highlights elsewhere in the region.