Places to see
20 mins by car
Cortona: a hill town of very ancient origins with spectacular views over the fertile Val di Chiana towards the hills of Sienna, and to the south towards Lake Trasimeno. One of central Italy's most interesting towns, the streets have a medieval and Renaissance flavour and the central square is one of the finest to be found in the area. The museums and galleries house paintings by Fra Angelico, Signorelli, Lorenzetti and Duccio to name but a few. Cortona hosts a festival in August and is also a centre for antiques and many other cultural and gastronomic events.
1 hour by car
Arezzo: An ancient town, famous for the fresco cycle by Piero della Francesca. The Giostra del Saracino takes place on the first Sunday of September is less crowded than the more famous Pallio of Sienna and certainly worth a visit.
Sienna: A must.
Montepulcinano, Pienza and Montalcino Beautiful hill towns where you can sample some of the finest wines in Italy and pecorino cheese, whist looking at some of Italy's most stunning architecture and views.
Perugia: Home to the National Gallery of Umbria and an ancient university city.
Citta di Castello
2+ hours by car
Florence: it is worth considering visiting Florence by train. There is a regular service from Camucia, which is in the valley below Cortona.
Places to eat
Valle Dame: at the top of the lane to Cerretella, a family run restaurant usually open at weekends.
Portole: on the way to Cortona, a friendly family run hotel and restaurant.
Castel Girardi: on the way to Cortona, with wonderful views and cool breeze on a hot day.
Trattoria la Grotta: in the centre of Cortona, reliable good food from a family run restaurant.
Trattoria Dardano: in centre of Cortona, typical Tuscan cooking with local ingredients.
Osteria del Teatro: in the centre of Cortona, good Tuscan cooking in elegant surroundings.
Molesini Wine Store and Market in Piazza della Repubblica, Cortona. Not only a good place to buy wine with expert advice, but during the summer they arrange gastronomic wine tasting dinners at local restaurants, definitely worth trying.