Day 1: Poggibonsi. Arrival in Poggibonsi, where you will be met by our representative who will drive you to your villa in Staggia near Castellina where you will enjoy an excellent supper.
Day 2: Villa Lecchi - Colle Vald'Elsa - San Gimignano. Departing from villa Lecchi, first you encounter the fortified town of Monteriggioni, its round distinctive shape dominating the surrounding plain. Then Colle Val d' Elsa and its glass blowing artisans some of which you can visit. San Gimignano with its towers will request more time and a couple of hours of window shopping before starting back to Villa Lecchi.
Day 3: Villa Lecchi - Castellina - Siena. A nice day through winding Chianti roads, in a landscape of luscious, vineyards and superb wineries to end in Siena to have an ice cream on one of the most famous squares in Italy: Piazza del Campo.
Day 4: Siena - Buonconvento. A nice day through winding Chianti roads, while the landscape is changing from luscious, vineyards to the more linear cypress-crested hills of the "Crete" near Buonconvento. Murlo is a nice little village on your way to the nice farm where you are spending the night. In summer you will be glad to get a refreshing dip in the swimming pool or in autumn a relaxing massage and a sauna at their beauty farm.
Day 5: Buonconvento - Montalcino. Rather difficult start, with fairly steeps slopes until you reach the asphalt. Then you head for The Monte Oliveto monastery. You will spend the night in a nice hotel in Montalcino the Brunello home land.
Day 6: Sant’Antimo abbey. Enjoy this fortified town from the bastions of which you will enjoy of a 360° view. The descending trail road lead you to the beautiful and peaceful church of Sant’Antimo where you may be able to listen to Gregorian chants.
Day 7: Montalcino - Pienza - Montepulciano. A full day as from the thermal square of Bagno Vignoni, to Pienza, the renaissance jewel redesigned by the pope Pio the II to become a "livable" town. Visit the town which is also an agricultural center well known for pecorino cheese, and truffle production. A dirt road will take you to Montichiello a nice little village immersed in the "Crete". You can stop there for a nice lunch or just for a cappuccino before continuing to Montepulciano known for its "Nobile" wine.
Also see tour packages in:
Europe Italy Outdoor: Land Rambler Bicycle Touring Cultural Journey