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Timing your visit to the Central Valley really depends on what you want to do there. January and February are peak summer vacation months in Chile, so the parks are open and the beaches are full. The weather will be clear and sunny—cool in the mountains and on the coast, and quite hot in between, making this the best time for many outdoor activities. If winter sports are your thing, your safest bet is to come from June to August, although the snow may last into September.
If it's the wineries that draw you to the Central Valley, however, consider that grapes are picked from late February through early May, depending on the varietal and area. This is certainly the best time to visit a vineyard, since you can see everything from crushing to bottling, and if you visit on a weekend, you'll also stand a good chance of finding one of the many harvest festivals that take place throughout the region at this time of year. But don't overlook a visit at any other time of year; the wineries offer tastings and fun activities year-round.