This is the country's oldest wine growing area. Its numerous vineyards and wineries are famed for their excellent reds, each with its own distinctive features, despite the fact that they come from the same varietals.
Within the valley, the following establishments may be visited:
-Viña Santa Carolina, 
it was founded in 1875 by Luis Pereira Cotapos, who named it after his wife Carolina Iñiguez. Its wines come from French varietals from the Bordeaux area (Cabernet Sauvignon, Cabernet Franc, Merlot, Sauvignon Blanc and Chardonnay). Its old mansion house and original cellars are located at Rodrigo de Araya 1431, Santiago.
-
Viña Cousiño Macul, this is considered one of
the best wineries in the world, and is also Chile's oldest. In 1546
it started out making wines for the Eucharist, and since 1856 it
has been owned by the Cousiño family. The guided tour of its cellars
includes an explanation of the manufacture of both red and white
wines, the history of the winery and, of course, a wine-tasting.
Its mansion house, cellars and park are located at 7100 Quilin avenue in Peñalolen.
- Concha y Toro, it was founded in 1880 by Melchor
Concha y Toro. This is the country's largest vineyard and main wine
exporter. Notable here are the beautiful European-style gardens,
the "Casona de Pirque", an impressive 19th century building, and
the original cellars. The tour includes a wine-tasting.
It is located 40 km south of Santiago, in Pirque, at 210 Virginia Subercaseux street.
- Undurraga, it was inaugurated in 1885, and is
one of the few vineyards that still remain in the hands of the founder's
family. These pioneers of the Chilean wine industry combine French
and German varietals in their vines. The tour includes a visit to
the mansion house, the storage cellars and the beautiful park. It
is located in the Melipilla area.
VALLE DE RAPEL
Its excellent cellars and an exhibit of Chilean rural customs represented by population lifestyle, architectural features and vine-growing methods are the main attractions of this wine-producing area located 180 km from Santiago.
Rapel, south of the Maipo, includes the valleys of Cachapoal and Colchagua.
-Valle de Colchagua, 
, this is one of the valleys in Chile that is most renowned for the excellent quality of its red wines. Harvest Festival celebrations start in March with a wine-tasting in Plaza Santa Cruz.
On the tour of its vineyards (more than a dozen), the excursions include, in addition to the usual wine-tasting and explanations of the wine-manufacturing process, getting to know the lifestyle and traditions of the valley's inhabitants.
A visit to the following Colchagua vineyards is recommended:
- Viña Santa Laura, its first vines were planted in 1979. Its low-volume though high quality production is mainly destined for the European and U.S. markets. It is regarded as the showpiece of the valley's vineyards. The bottling process is well displayed.
- Viña Bisquert, considered a pioneer in fine wine production, this vineyard is over 150 years old, although it only began bottling its own brand of wine in 1991. Its modern production technology makes a picturesque contrast with its venerable dining room and the exhibit of horse-drawn carriages that are included in the tour.
- Viña MontGras, this winery was founded in 1992 to produce quality wines using state-of-the-art technology from grape reception up to bottling. Over 90% of its production is exported to European, North American, Latin American and Asian markets. The wine-tasting of its excellent production takes place on the slopes of a nearby mountain, affording a majestic view of the valley below.
- Viña Viu Manent, this winery features a French-style mansion house.
- Valle de Cachapoal, This is a novel tour including
a dozen wineries, in which a wide variety of varietals such as Merlot
and Carmenere are grown. The most important vineyards are those
of Chateau de los Boldos (the oldest in the valley), Gracia, Anakena,
Morandé, Hacienda Los Lingues, among others.