From northern Italian cities the two most popular routes for pilgrims and others on the way to Rome by car or train are either following the coast through Livorno or inland via Florence. But it wasn’t always Livorno or Florence: Siena in Southern Tuscany was once an important staging point on the way south or north to or from the capital and it stuck in the memories of travellers more than most places. It is the best of the best places to visit in this section, alongside the cluster of convents, monasteries in the vicinity which propsered on the passing trade of travellers.

Southern Tuscany is a pleasant contrast to northern Tuscany, less manicured, more countrified but full of gems such as the hill-top town of Pienza. In the north of the area, San Gimignano is a tourist hotspot, whereas neighbouring Volterra is just as interesting, but less overrun.

To stay, check out La Foce, a family-run estate with panoramic views. Or try Castello di Potentino, an old watchtower-turned-hotel, producing artisan wine on site. In Pienza, just outside of Montepulciano, La Bandita Townhouse is a comforting refuge. Further north in Volterra, we recommend Villa Rioddi – a spacious villa with incredible views. Castello di Gargonza in Arezzo is also a good choice.

TRANSPORT

There are no aiports. Two railway lines run south-east from Siena, one to Chianciano Terme and the other to Monte Amiata. Siena’s sation is below the city, a 10-minute bus ride fromn the centre.  Frequent and prompt country buses link all the towns and villages marked on the map.