Montalcino is part of the provincia of Siena. You can get there without a car by using the bus service that leaves from the Siena train station , number 114, or in several places along the utside walls. One of the best places to get it is at the base of the moving staircase that goes to and from Piazza San Francesco, at the end of via dei Rossi. Or Porta Pispini, or Porta Romana. Get your ticket before from a tobacchaio, as they never have them on the bus. The bus also stops at Buon Convento, where the trains also go, both from Siena and Grosseto (your connection to Roma).
You can enter the city through its orginal fortified wall in several places.Be prepared to walk up a steep incline, unless you use the threee moving staircases, one near Porta Ovile, that goes to San Francesco and via dei Rossi, one near Porta Fontebranda that goes near Piazza San Giovanni, near the Campo, and a third that leaves from the Train Station and goes to the entrance at via Camollia.
Montalcino is home to one of the rare pentangle fortresses, which, in all the wars between Firenze (Florence) and Siena, was never taken.
There is also an exquisite Museum, with an extremely beautiful and lifelike Madonna that has become one of the city's symbols, carved in the 15th centruy by the famous anonymous..noone knows who. It is in part of an original convent , with the traditional central courtyard and orange trees. Concerts and the first tasting of the year's Brunello are held here, as well as lectures and other events.
It is well worth the time to see the four museums of the Sagre, the traditional Archery contest that is held twice a year in Medieval-Early Renaissance dress. The four "Quartieri" compete with all their heart, soul and voice in a challenging contest with small cutouts of a wild boar, at 25, 30, 35 and one of the team's choice up to 45 meters away, often with a stiff wind blowing, at the back of the Fortezza. The concentration of the archers is impressive, among shouts from all sides trying to disconcert them. Some of the archers have gone on to the Olympic tryouts and National competitions. The Sagra, also a time to eat local specialties and drink the various forms of the great wines, both the Rosso and Brunello, and the Moscadello, for which Montalcino has been famous throughout the centuries.
Montalcino includes five other smaller towns, the 'Frazioni', which each have their charm and breathtaking views. Sant'Angelo in Colle,known for its two excellent restaurants, Torrenieri, which used to be known for its difficult turns and twists and the bike and motor competitions, and the biggest of the five, Sant'Angelo Scalo, also known for its simple restaurants which have surprising and excellent food, Camilliano, tiny and sweet, Castelnuovo dell'Abate, where the quietly qnd utterly amazing Sant'Antimo Abbey lies nestled among the vineyards and ancient olive trees. At one time one of the most famous Abbeys of Tuscany, it was built by Carlomagno,in gratitude for having been spared the Pesta, the Great Plague of his times. The Cisternian Monks sing all of the several sevices in Gregorian chant. And of course, the history of that place goes long before the Christian religion was ever born. A sacred site to the Etruscans and before, a place where there is a sacred Source, each generation has reverberated to the mystical and potent peace that the place emanates. It is not to be missed.
Nearby is another Tuscan wine town and Montalcino's rival, Montepulciano.