Montalcino is a smallish hill town in southern Tuscany, and it's where we decided to base ourselves during our 5-day trip through the region. It's known to wine lovers as the origin of the delicious Brunello di Montalcino, or its less expensive sister, Rossetto di Montalcino. Needless to say, we basically had red wine running through our veins by the end of this part of the trip.
We'd read in our Rough Guide to Tuscany & Umbria about some private accommodations, which we decided to check out instead of staying at aproper hotel. I wish I could recall the name of the place we stayed; it was more like a few rooms in someone's apartment over a bakery - so I can't recall if it even had a name! But it seemed like most places to stay in Montalcino would be charming and very affordable - about $20-$40 per night total. But I'd suggest booking ahead, as there aren't many placesfrom which to choose. We called ahead from the side of the road on our way! :)
The town turned out to be a perfect base for lots of day trips, as it's centrally located between some of the most well-known and fun to visit hill towns of Tuscany, including Pienza and Montepulciano among other smaller towns, as well as nearby some wonderful sights including Monte Oliveto Maggiore and San Galgano (all written about more in this journal).
At night we'd come back to the town, freshen up and have dinner at one of the half-dozen informal, bustling little trattorias, which by day overlook the sweeping vistas of the Tuscan hills, and by night are filled with locals eating and chatting. And then we'd retire to the one main bar in the "center" of town where we'd play cards, practice our Italian with the bartender and customers, and of course drink the delicious vino rosso!