Helpful links for Visit Chile

Google Maps Chile
Airport Shuttle in Santiago

Wine Train & Wine tasting in Chile

Photo title:Red Wine Grapes
via Flickr

It's very easy and feasible to do a wine tasting day trip or overnight trip from Santiago. The roads are very nice in Chile - you'll have no problem and they're nothing like the awful roads you read about in Bolivia where accidents happen.

There's also a wine train from Santa Cruz. Be careful that you check in advanced with your hotel, as it only runs on weekends in the low season.

In the Colchagua Valley the Vina La Playa Hotel is most highly recommended for it's central location among wineries and a vineyard. The drive is about forty minutes from Santa Cruz and there are wineries along the way.

Also, a day trip to the Maipo Valley is very feasible as well. You can get a van tour to handle multiple vineyards in a day, which makes things a bit easier so you don't have to worry about driving drunk.