Casole d'Elsa is around half an hour from Siena and 40 minutes from Florence, so ideally placed for exploring Tuscany. Should you decide to simply stay local and relax, there is plenty to explore and to enjoy. The village is structured around a single main road, with the main church at one end and the town hall at the other. The fortifications that once encircled the whole town are still largely visible; one of the old bastions and defensive towers has now been transformed into a delightful hotel, Torre dei Serviti.
The main church is the "collegiata di Santa Maria Assunta", consecrated in 1161;
damaged during the second world war, and later stripped of its 18th century decoration, only parts remain of the original Romanesque façade. The transept is from the 14th century and the interior has the tombs of Beltramo Aringhieri, by Marco Romano (early 14th century), and of bishop Tommaso Andrei, by Gano di Fazio (1303). Annexed to the church is a Museum of Sacred Art with works by Domenico di Michelino, Alessandro Casolani as well as a lovely collection of Etruscan artifacts from the many tombs found in the nearby tufa outcrops.
The church has a cloister that is often used for classical concerts and theatre:
In front of the church is "Bar Barroccio", the perfect place for breakfast, not to mention a spot of lunch - they do excellent bruschette, or large salads. It's also a great place for an aperitivo, sitting outside in the evening with an "Aperol Spritz" or simply a prosecco. Next door the Pizzeria/Ristorante "Il Porrina" has a large covered outdoor area and a very good menu.
Walk up the main street toward the Castle that house the town hall and you'll pass a number of galleries housing works by local artists as well as the Caffe Casolani, a fantastic restaurant with a fixed menu - it changes all the time but on any given day you'll just get that day's menu. There is something wonderfully relaxing in this era of choice, choice and more choice, in the experience of sitting down and allowing somebody to simply start bringing you dishes - each one delicious and each one a surprise.
At the other end of the village is the world-renowned Verrocchio Art Centre offering fine art courses, painting holidays, sculpture courses, studios and accommodation. Nigel Konstam is the resident director and a sculptor whose work is firmly based in the European tradition.
We have a number of villas for rent close to the village - many people's favourites are the simple apartments of Agriturismo Elvira: Pinolo for 4, Noce for 2 and Rustico for 4. They are a 10 minute walk from the village so a perfect combination of bucolic peace and close-by restaurants and cafes. For those who prefer to be right in the mix of things we have flats in the village, like Musicista, right on the main street.
A view of the alleyways in Casole d'Elsa - the tractor is parked outside the village olive mill, so I must have sketched this in November: