San Gimignano
To reach San Gimignano we will pass through the most wonderful Tuscan countryside — classic rolling hills, neatly-rowed vineyards and silvery-green olive groves, a living picture postcard!

San Gimignano, “the Manhattan of Tuscany”, is best known for its watchtowers that were a display of power and prosperity in Medieval times. Although only 14 of San Gimignano’s original 72 towers remain the effect is still dramatic and will give you lots of great photo opps.

Take your time strolling the narrow cobbled streets and open piazzas, and be prepared to step back in time. Art lovers may wish to spend some time in the church of Sant’Agostino to see the charming cycle of frescoes by Benozzo Gozzoli as well as a substantial selection of paintings and sculpture by some of Italy’s major Medieval and Renaissance artists. San Gimignano is also home to award-winning gelato; look for it in the main piazza.

Montepulciano
Nestled in a particularly lovely and much-photographed area of Tuscany, Montepulciano is a classic Medieval village with a refined edge.

Montepulciano is known for its Vino Nobile, but there are many other things to enjoy if you prefer art and architecture to wine. Stroll the sloping, narrow streets and you will inevitably end up at one of many lookout points giving you spectacular views of the rolling countryside.

The main piazza, Piazza Grande, is a beautiful composition of the elegant Renaissance palazzi of important families, the brooding Gothic figure of Palazzo Comunale, the unadorned facade of the cathedral, and Pozzo dei Grifi, a fancy well decorated with lions, griffins, and the Medici family crest. Fans of the Twilight books might recognize Piazza Grande -- it was a shooting location for the New Moon film.

A novelty in town and an emblem of the city is the Torre di Pulcinella. The clock tower is topped by a puppet character from 17th century Neapolitan commedia dell'arte who strikes the bell on the hour to mark the time.

There are a good many churches to visit, for either their architectural beauty (such as San Biagio) or the important artworks they contain (Sant'Agostino).

CHURCH DRESS CODE
Proper attire is required to enter churches (bare shoulders must be covered and shorts/skirts must come down to your knees).