The experiences we'll convey are from the several days we spent in the region on our honeymoon in October, 2005. The map should help get your bearings.

We'll focus on the roughly north-south axis running from Firenze (Florence) through Siena and down to wear it Ts-off with the east-west axis between Montalcino and Montepulciano. We'll focus on three areas that produce three wines which are deemed DOCG (Denominazione di Origine Controllata e Garantita): Chianti, Brunello di Montalcino and Vino Nobile de Montepulciano. All three of these wines use the Sangiovese grape (or one of its clones) as their majority ingredient. We'll save focusing on the wines themselves for our tasting.
The Chianti DOCG is divided into eight sub-regions. The autostrada from Florence to Siena bisects the Chianti Classico sub-region (where Chianti originated) with stereotypical Tuscan vistas on either side. Soon after passing the half way point between the two cities, there is an exit to the tiny town of Montereggioni whose towers are old enough to have had a cameo in Dante's Divine Comedy (Inferno, xxxi. 41-44).
Montereggioni lies near the border of the Chianti Classico and Chianti Colli Senesi regions. We stopped for lunch, a little exploration, and to enjoy the view from the hilltop.
That night we went on to our bed & breakfast just outside Siena.
The next day we explored beautiful Siena. The following day it was back to the hills, but this time south of Siena. By lunch time we reached Montalcino and found some proscuitto, pecorino cheese, and bread for a little picnic with a half bottle of Brunello just outside the town's castle.
From there we had a view of the hills descending down from Montalicino's perch.
Unlike Siena and Florence, wine is front and center in Montalcino -- a large map of area wineries is in the main square. Having just served a favorite from Banfi called Col di Sasso at our wedding, we decided to try to find its source. Heading south we quickly descended into the valley as the sun broke through the clouds. We drove past vines on either side from a variety of producers, and as we got closer to the valley floor began to see the logo indicating we had found Banfi's 7,000 acre estate. Banfi is a relatively recent American-owned addition to the Montalcino wine scene. (Montalcino itself has really only gained prominence in the last half-century or so.) Banfi's central "castello", however, dates from the middle ages, at least.
Unlike many Italian producers, Banfi has a consumer-friendly retail operation, though at the time it had no tasting facility other than its restaurant.
From Banfi we decided to head east, eventually ending up in Montepulciano around time for our evening meal. Montepulciano is a bit more imposing and engrossing than Montalcino, though its signature wine, Vino Nobile, is often in the shadow of its cousin Brunello. We enjoyed exploring it at dusk.
The restaurant we had our eye on turned out to be booked solid, so we tried a one-man trattoria next door. As dinner progressed (with a half bottle of Vino Nobile), we were pleasantly surprised to learn first that the pasta dishes were fairly tasty and second that our seemingly passive server/chef/barkeep was an aspiring opera singer.
He sang along energetically and quite capably with the great tenors on the stereo. That evening we returned to our B&B and the next day set out for northern Tuscany and eventually on to other destinations (see other pictures).
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Tuscan Wines we're tasting:
Castello Di Monastero, Sangiovese, 2004
Castello Di Monastero, Chianti Classico, 2004
Avignonesi, Vino Nobile di Montepulciano, 2004
Siro Pacenti, Rosso di Montalcino, 2003
Capanna, Brunello di Montalcino Riserva, 1999
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