Known for its spectacular Duomo di Orvieto and Giant Cistern, this hilltop also has lots of great Michelin star restaurants, fantastic shopping, and a world-famous Jazz Festival.

Almost every town and city will have a nice cathedral, but Spoleto also has the impressive Ponte delle Torri Roman Aqueduct, 1st Century Roman Amphitheater and 14th Century hilltop fortress Rocca Albornoziana. If you come in the summertime enjoy the Spoleto Festival featuring concerts, Italian opera and dance troupes.

The birthplace of St Francis of Assisi is a UNESCO World Heritage Site whose crown jewel is the Basilica of St Francis, visited by millions of pilgrims yearly.

The regional capital of Umbria has a charming medieval center with lauded restaurants and shops, but come for their famous Perugina chocolate. It also hosts a Jazz Festival; I guess Italians love their jazz music.

You might be familiar with this Etruscan town if you came in by train from Rome, but its old town centre has fascinating underground tunnels and an archaeological museum.

Renowned for its wine, the Vino Nobile di Montepulciano, this hilltop town also has stunning views of the Tuscan countryside and a large Christmas market. The way up to the top is a little steep but very charming, and if my 80 year old mother can make it, so can you.

Lovely Pienza is a UNESCO World Heritage Site for being the ideal Renaissance city. That it makes the world famous Pecorino di Pienza cheese is a bonus!

This is the city featured in “Under The Tuscan Sun” with Diane Lane that popularized Tuscany to the world, but we found it touristy and charmless. Nice views though.

A charming town in the beautiful Val d’Orcia, famous for its cypress lined avenues and beautiful scenery. My only warnig if you go, you might not want to come back.

Everyone loves Siena. The whole medieval centre is a UNESCO World Heritage Site, including the Piazza del Campo where the Palio di Siena horse races are held every July and August. If you go, the Taverna di San Giuseppe makes the best ribollita (Tuscan bean soup).

Known for the Fiera Antiquaria, the oldest flea market in Italy held every first Sunday of the month. The historic centre is charming, but then all of them are.

This “Dying City” is perched on a hill accessible only by a pedestrian bridge. It is slowly crumbling to oblivion, which you can see by building facades with nothing behind them but chasm. See it before the whole thing falls down.

This medieval city is known for its thermal baths and a well preserved Papal Palace.

This lakeside town has a cute historic centre but also the opportunity for water activities on Lake Bolsena in case you’re tired of the green (but how can you be?)