Siena

Siena is undoubtedly one of Tuscany’s loveliest medieval cities. The UNESCO World Heritage listed medieval center overflows with striking gothic buildings and you can fill an entire day just losing yourself in its narrow winding streets and hidden squares. Its cathedral is one of the most spectacular within Italy, and the Piazza del Campo, build on the site of the Roman marketplace, is perfect for indulging in people watching and Italian café culture. For something different, the Siena Jazz School (which is in the Medicean Fortress) runs concerts all year round.