The Ultimate Chilean Wine Trip in 6 Days

Days 1 and 2: Santiago and the Maipo Valley

Start your oenophile adventure in the capital city of Santiago, from where some of Chile’s best wineries are only a cork’s throw away in the Maipo Valley. Look for bilingual tour availability and accessibility to public transit. The most fun time of year to visit is during the February to May harvest season, as many festivals and celebrations are held with unique opportunities to participate.

Book your winery tours at least 24 hours ahead to ensure the availability of an English-speaking guide. Private, personalized tours may be available depending on the establishment. Our top recommendations include Viña Undurraga, started and run by the same family since 1885; Viña Concha y Toro, Chile's largest wine producer and perhaps its most entertaining winery tour, with a visit to the Casillero del Diablo, the famed wine cellar where the devil supposedly dwells; and Viña Santa Rita, with an impressive on-site museum and Pompeiian-style manor.

Days 3 and 4: Casablanca Valley

From Santiago, it's a mere 45-minute drive to the Casablanca Valley. Just three decades ago, the land here was considered inhospitable for vineyards, but now winemakers have discovered that the valley's proximity to the sea is its main asset, because cooler temperatures give the grapes more time to develop flavor as they ripen.

The three can't-miss vineyards in this area are Casas del Bosque, which offers a vineyard tour in an old wagon; Viña Matetic, whose stunning bodega resembles a bunker worthy of a James Bond villain; and House of Morande, which is one of the valley's oldest wineries and a superb place to stop for lunch during your tours.

If you grow tired of vineyard-hopping, make your way to Viña del Mar, a mere 30 kilometers (18.6 miles) away from the heart of the valley. It's a great place to spend the night while exploring the Casablanca Valley. You can walk along the beach in the morning and then indulge in the vibrant nightlife when you've returned in the evening.

Days 5 and 6: Colchagua Valley

From Santiago, drive 90 minutes south to the Colchagua Valley. Stay overnight at an inn or B&B in Santa Cruz, the main town of the valley, with an attractive central square and several craft shops. There are numerous vineyards to visit throughout this valley, but one of the better ones to start with is Viña Montes. It's known for its deep reds, crisp whites, and feng shui design principles. Nearby, Viña Lapostolle-Clos Apalta is housed in one of the most handsome pieces of architecture in Chile: the barrel-stave-shape beams rising impressively above the vineyards create a wooden nest for the winery, which is built into a hillside to facilitate the gravity-flow process.

Be sure to make time to visit Viña Santa Cruz, which is really an entire wine complex. It features a cable car, astronomical center, and indigenous museum. Plan to spend several hours here.

Transportation

There are a variety of options available. If you prefer the independence of a self-guided tour, rent a vehicle in Santiago and pick up a map of the Chilean wine region, which is available at many bookstores and wine shops. From Santiago to Casablanca, you can take a public bus and then a taxi from the terminal to your wineries of choice.

Most organized tours are offered as either half- or full-day, and include guides as well as meals. There are alternatives to the tedium of bus tours; options can combine horseback riding, bicycling, and even zip-lining along with your wine tastings.