Meet your guide and then head out of Siena, going south to Montalcino, a hilltop town of medieval churches and cobblestoned streets that is famed for the wine it produces: the lauded Brunello di Montalcino and its more affordable sibling Rosso di Montalcino.
On the way there, learn about the history of the town from your guide, as well as, about the wine production around the town. Hear what makes Brunello one of the world’s best varietals. Upon arriving in town, spend some time on your own, strolling the streets and popping into one of the many enoteche, the wine shops that double as bars, where you can drink wine right there on the spot or purchase a bottle or two to drink later. Or stroll up to the 14th-century fortezza, the imposing castle at the top of the city, where you can get a stunning view of the the classic Tuscan countryside: the rolling hills, the villa-crowned hills, the vineyards.
At a pre-arranged time, meet up with your guide again and go to nearby Abbazia di Sant’Antimo, an incredible Romanesque church made with Travertine stone that is set in a tranquil valley. The abbey is a typical stop for pilgrims who are walking the Via Francigena, a long medieval pilgrimage route that stretches from Canterbury in England all the way down to Rome.
Inside the the abbey, gawk at the early Renaissance-era frescos and the sunlight that shines in from the windows. If luck is on your side, the may be a live Gregorian chant happening by the monks who live in the abbey.
After lingering around the abbey for a while, board the bus and head to a nearby winery to conclude the trip on a ruby red-colored note: sample some of the local wines including Brunello di Montalcino and a few other locally produced wines.
Go back to Siena in the early evening having just had a satisfying day exploring southern Tuscany.