San Gimignano is known as the Manhattan of Tuscany for its skyline of remaining defensive towers. At one time as many as 72 towers loomed above the valley surrounding this hill town. Residents knew the value of vertical space and surrounding the triangular town square are town houses of four and five stories.

Encircled by 13th-century walls, this town was a stopping place and reference point for anyone traveling along the Via Francigena road and pilgrimage route leading to Rome, serving as a protected place of respite. One can stroll the narrow streets to find chapels, fountains, frescoes, and beautiful detail in the stonework.

If you happen to be in the area in June, be sure to attend the Ferie delle Messi or Medieval Harvest Festival. Step back in time into a fertility festival, which dates back to 1255. Contests between four distinct neighborhoods compete to win favor of the fertility gods. Archery, tug of wars, exhibitions, entertaining shows, and tests of skill between knights lead to the most awaited moment of the festival: the Corteo delle Messi or Grand Procession, where over 500 people in medieval costumes parade through the streets.

The weekend festival culminates with the blessing of the horses that will carry their knights in a final battle of skill and bravery.