If you really want to learn about a region, as opposed to learning about the most expensive wines of a region, you'll have to start from the bottom up. Well, you don't necessarily have to start there, but you'll have to go there and you might as well make it your first stop.
For example, you can learn about Montalcino and Brunello by drinking Brunello, but a better approach is to begin with Rosso di Montalcino. Why you ask? Three reasons.
They are less expensive.
The are generally ready to drink on release and not in need of cellaring.
They have less of a winemaking influence.
This last point is a doozy. Because of law or effort, more expensive wines often show more of a winemaker's hand. If you really want to learn about a region, start with the simpler wines.