This article, recently published on the BBC website describes how the little town of Montalcino has managed to grow and infact develop significant largess on it's exclusivity.
http://www.bbc.co.uk/news/
I came to Italy knowing nothing about Italian wine - I had heard of Chianti and that was about it. I will leave Italy, knowing a little more, but having only scratched the surface. Here I will try and encapsulate a few points.
1) Booze is cheap, super cheap. You can buy wine for less than 99c for a bottle. It's barely bearable. However, you can go to filling stations, along with your demijohn and fill up for significantly less than this and have perfectly drinkable table wine. This is blended wine that hasn't made it to DOCG and is just cracking. Local beers are very cheap, approx. 50c for a large bottle when on offer, mainly Moretti.
2) You can buy a really good bottle of wine for a very reasonable price. At around 4 EUR you have a good bottle of wine if you know what you're looking for.3) In Tuscany, noone knows about white wine. Caveat: In San Gimignano there is Vernaccia, which is kinda ok, but not great, and most wines are red in the region.
4) Proseccos are great and always cheap. But but but, avoid at all costs anything sweet (dolce). If you follow this rule and go for a prosecco superiore you can get a really really excellent bottle for about 6 EUR.
5) You get what you pay for. When you start paying more than 20 EUR a bottle you get some great wines, unlike in the UK where it seems a bit random.
6) I don't like Chianti. I lived for more than 3 years on 2 estates that made Chianti. Good Chiantis, to my taste are very few and far between - however, there are some crackers. I really like the Dievole Riserva (http://www.dievole.it/en/home/home.aspx).
7) Amarone is great, although I prefer the softer Valpolicella.
8) Brunello is overpriced.
Ooooh - wait a minute! Isn't this defying the point of my article. Well, yes it is - but yah boo sucks. Brunello is a 100% Sangiovese and if you pay 30 EUR or more for a bottle, from a shop (not from some restaurants) you will get a fantastic bottle of wine. Avoid cheaper bottles as you will be disappointed.
http://en.wikipedia.org/wiki/Brunello_di_Montalcino
However - when you taste a lot of Brunellos you start to appreciate the diversity therein. Although DOCG (Denominazione di Origine Controllata http://en.wikipedia.org/wiki/DOCG) it really varies a lot. If you don't know what you are buying or what you really want then I have some other suggestions.
Brunellos are grown in a certain way in a certain region in Montalcino. For a slightly cheaper price, you can go for a Rosso di Montalcino which I think, honestly, offers far better value for money in a restaurant if you don't know what you are looking for.
Just over the hill from Montalcino it Montepulciano. From here you find the fantastic Vino Nobile di Montepulciano (http://en.wikipedia.org/wiki/Vino_Nobile_di_Montepulciano) which in my mind are almost as good as Brunellos, but just because they do not have the cachet of Brunello, they are half the price generally so I will strongly recommend trying one of these. Of course, do not confuse with Montepulciano D'Abruzzo which is a different kettle of fish.
Montalcino itself is a cute little city, with a rather fantastic pentagonal fortress. The city has been involved in some of the older tuscan battles, as the strongholds of Florence and Siena smashed through the area.
However, beyond the scenery and the wine there is very little there. A couple of cute squares, a nice view - it is rather high up in the area - and of course one of the main towns on the route of L'Eroica (http://www.eroicafan.it/en/). Within the town you will find in every place the possibility to taste and sample the wines and especially the Brunellos. I see three main options:
1) Cafe - the cafes will set up a little wine tasting for you. Pick some wines from the list and they'll slap them on your table with some brief history. Replete with some classic tuscan food - you know the crotini misti, pecorino with honey, meats, yadda yadda yadda.
2) The restaurants. These will do something similar to the cafes. Typically you can choose a tasting menu of three wines and brunellos (isn't this also a wine?!) from a standard list to go with your food. I have had this with some cinghiale and polenta which really compliments the wine - as long as it's not stinking hot!
3) The shops. The shops are great. Particularly the ones that you can buy a charge card, take a glass, and help yourself to a tot of each one that takes your fancy. When I have been, if you buy some wine, they will subtract the cost of the card and the sampling. It's a great way in and these guys typically know the wine very very well. Of course, they are very Italian, so will be a little caged at first to foreigners, but if you can show some interest and some passion, they will reciprocate in buckets.
Also, we have had some success with them posting wines back to the UK, in good condition, for a very good price. Give it a go.
Attached I have a lot of photos. Some random, some less so. Some of the tastings. Some of the shops where you buy wine. Some of the local area, the Crete region, and also some of it in the snow. It's all good.
Every year when the new Brunello comes out there is a large festa. Each year there is a new plaque laid down celebrating the new Brunello. Here are a few pics of those plaques. 
This year the Robbie Coltrane was really in with the nonnas of the region. Really. Could not have told the difference in a line up between several of these women and Robbie Coltrane. A-maz-ing.
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