Country roads wind around cypress trees on hilltops that often appear to catch and hold onto the clouds. Planted vineyards, fields, and orchards turn those curving hills into a patchwork of colors and textures that have inspired artists and delighted travelers for centuries.
Sitting majestically in the midst of all this natural splendor is Siena, longtime rival of Florence and one of Italy's best-preserved medieval cities. Other hilltop towns will beckon you as well: San Gimignano, with its lofty towers; the ancient city of Volterra, once capital of a flourishing Etruscan state; and myriad charming villages dotting the rolling hills of Chianti. The rolling hills are the region's most famous geographic feature, and you can expect to do a lot of winding up and down on panoramic roads that link the area's hill towns. The narrow medieval streets of these old town centers are mostly closed to traffic. Park outside the city walls and walk in. Just keep in mind that roads often lack shoulders in these parts.
Siena fills to the brim in the weeks surrounding the running of the Palio on July 2 and August 16, when prices, crowds, and commotion are at their highest. Between May and late September, hotels and restaurants throughout the region fill up, and foreign license plates and rental cars cram the roads. There's a reason for the crush: summer is a glorious time to be driving in the hills and sitting on terraces.
If you want fewer crowds, try visiting during spring or fall. Spring can be especially spectacular, with blooming poppy fields, bursts of yellow broom, and wild irises growing by the side of the road. Fall is somewhat more soothing, when all those colors typically associated with Tuscany—oranges, warm ocher, mossy forest greens—predominate.
In the winter months, you may have towns mostly to yourself, although the choices for hotels and restaurants can be a bit more limited than when the season is in full swing. From November through mid-March it's fairly difficult to find a room in San Gimignano and Volterra: plan accordingly.
