This wonderful Tuscan hillside village is particulalry special as it's where I grew up and went to school so it has a place in my heart.
Set on a ridge west of the Elsa valley, still framed by the medieval walls, Casole d'Elsa has several good restaurants, cafes, a couple of grocery stores, a butcher and an excellent ice-cream shop. There is one main street that runs the length of the town (town's a big word but go with me) and during the summer it's closed to traffic, so that everybody can walk up and down - particularly the teenagers - checking each other out. This is know as doing 'le vasche' or doing lengths. You walk from the the old town hall all the way down to "Luciano's Bar" (Bar Barroccio) and then back again. As an encouragement Antonella, close to the Town hall, sells excellent ice-cream, and Bar Barroccio at the other end of the village makes very good Aperol Spritzes.
During the summer there are often concerts and events - we even have our own Palio, as horse race up the hill in front of the village. The race is usually on the second Sunday of July and after the race there's usually an excellent outdoor roast dinner with long tables set up for all the village. There are often concerts organised, from open air opera, classical music and more, as well as exhibitions and markets.
It's a lovely village for getting a taste of Tuscan village life - children will be feted and enjoyed, all the restaurants are good, some more than others and the village swimming pool is great if you have teenagers to amuse.
We have plenty of houses in the area and some in the village itself - these can be perfect for an out of season escape, a relaxing autumn stay or even a May half-term trip with the kids. Have a look atPinolo for a place with a pool nearby, or at Poeta or Rondine if you'd rather be in the village itself...
Below is a drawing of mine from 1995 of the small cloister of San Cristoforo where concerts are sometimes played.