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Travelling south from Arezzo you pass through the rather flat and uninspiring Valdichiana (this is drained swampland, reclaimed along with the Maremma by the Etruscans, and now prime cattle country), flanked by numerous hilltop towns, the finest of which is undoubtedly Cortona. Visible from all around, a five kilometre drive through vineyards and olive groves, passing the splendid Renaissance church of Santa Maria delle Grazie en route, will take you up and up towards the town, dominated by the ubiquitous Medici fortress.

Cortona is surrounded by ancient fortified walls, and this built in planning restriction has meant that nearly all new development has occurred lower down the hill, leaving Cortona as a delightful mediaeval town to explore on foot.

Cortona is blessed with numerous very good restaurants, many of which are just a moment or two from the main focus of Cortona, the central Piazza della Repubblica, dominated by the Town Hall and the steep steps leading up to it - the ideal grandstand for watching the busy little town pass by. Unless they're relaying the ancient flagstones, as they were when we were last there, that is.

A short hop from here is Piazza Signorelli, home to the theatre and the Museo dell'Accademia Etrusca, which in turns leads into the Piazza del Duomo, home to the Cathedral and yet another panoramic vista from the town walls.

If you truly want to be monarch of all you survey then you'll need to trek up to the top of the town and the Medici fortress, where you'll be afforded some incredible views of the surrounding countryside and down towards Umbria and lake Trasimeno.

and some history:

Legend has it that Dardanus, founder of Troy, was also the founder of Cortona. Already a sizeable settlement, then in Umbria, it fell to the Etruscans around the eighth century. Next came the Romans and then the Goths, who destroyed Cortona for the first time. The town became independent, constantly battling with Perugia and Arezzo, the latter being responsible for another destruction in 1258.

Next came the patronage of Siena, giving rise to a quick revival of fortunes. Fast forward to the fifteenth century and the Kingdom of Naples stakes a claim, only to sell Cortona to the Florentines and hence a return to Tuscan tutelage, a state of affairs that was never again to change. So, whereas there are Etruscan tombs and an Etruscan museum, it is the air of mediaeval times that accompanies as you stroll around Cortona. Well, OK, you won't always exactly be strolling - hilltop towns have hilltop streets, some of which are quite steep.