Dotted across the whole region are, of course, many of Italy's most famous citta d'arte (art cities),  whose names everyone knows:  Florence, Siena, Volterra, San Gimignano, Perugia, Assisi and Gubbio.  But these are only the diamonds in the tiara (and perhaps suffering in recent years from the depredations of mass tourism - they are best seen out of high season unless your idea of a holiday is to stand in long queues for a three-minute ogle of David). 

Less well-known gems abound throughout the two regions:  Montefalco, known as Umbria's balcony for its remarkable outlook; Trevi, with its dramatic mountain-side location; Pienza, a delightful and unique remainder of Renaissance town planning; and San Piero a Sieve, in the Mugello, whose ugly outskirts belie its medieval heart.

Much of the delight of traveling this region lies in ignoring the standard tourist trails and just following the road.  Do this, and you will always be sure of arriving at some memorable destination which, may well not yet be 'discovered' - by the tourists, or the guide books.

In Tuscany and Umbria, like the rest of the country, most towns have their own local holidays, usually the feast day of the patron saint, often celebrated with a fair and fireworks.   In addition to these are traditional events and festivals peculiar to each locality: Siena has its famous horse-race in Piazza del Campo (the Palio); in Arezzo, they joust in full medieval costumes; in Florence, they still play a lethal version of traditional football (calcio in costume); in Gubbio, teams of young men run up and down a steep mountain carrying gigantic wooden 'candles', apparently just for the fun of it.  Religious pageantry is particularly rich around Easter and food and wine get their turn in the autumn with fairs ('sagre') devoted to tasting of local specialties: Chianti Classico, truffles (in Umbria), pecorino cheese (in the Pienza area), boar, and olive oil.  Details can be had from local tourist offices, or keep an eye out for posters.