Tuscany stirs the heart and mind like nowhere else. It’s a feeling that can really only be satisfied by experiencing the history, art, culture and cuisine for yourself – and, if you do, it’s guaranteed to be the beginning of a lasting love affair.

The sunburnt patchwork of Tuscany’s landscape is defined by its scattering of fortified hill towns; the following five are often on the itinerary of the best small group holidays to the region. Each has a unique personality, but all are characterised by the beautifully preserved medieval architecture, warm-hearted locals and, of course, the unparalleled food and wine culture for which this region of Italy is so renowned.

Montalcino

Situated in the central province of Siena, Montalcino’s reputation for producing exceptional wines – including the world-acclaimed Italian red, Brunello – makes it a valuable addition to the itinerary of small group holidays with a focus on food and wine. It’s the perfect place to reacquaint or enjoy a first encounter with this superb wine at its source.

With far-reaching panoramic views over the countryside, the ancient streets and charming architecture of Montalcino reveal its history and culture in a very tangible way. For lovers of jazz, the annual Jazz & Wine Festival held in the town every July is another compelling reason to visit.