I am sure you all know major art cities and travel destinations of Tuscany like Florence, Siena, Pisa, Lucca, Chianti, but have you heard of Lucignano, Monte San Savino, Castiglion Fiorentino?

There is a special excitement in discovering the unexpected beauty of places you have not known the existence of, and if you follow me (now virtually, hope soon in person) in the exploration of these off-the-beaten-path destinations of Tuscany, you will be impressed at how interesting, rich of character and history they are.

Do include in your next  trip to Tuscany a guided visit of Valdichiana, the green open valley that starts south of Arezzo and whose spectacular view one enjoys from Cortona. The hills around this beautiful plane are dotted with charming hill towns, ancient Borgos and medieval castles that bear that charm of times long past, still permeated by a special atmosphere and where small communities hold on proudly to their genuine lifestyle.

Lucignano bears one of the most characteristic medieval urban settings identified by windy concentric streets that focus on the centre of the settlement  - the highest point of town - where the symbols of religious and political power are, the Collegiata church and the Town Hall. A guided walk through this small jewel of Tuscany reveals the important role it had in the past centuries, and will make you admire a few unique pieces of art among which the famous Tree of Love, a medieval reliquary in the shape of a tree in front of which couples share their promises of everlasting love.

Also Monte San Savino has a characteristic walled historic centre that reminds us of the Middle Ages, when communities had to protect themselves from recurring attacks. Did you know that this small town boasted a huge Jewish community and that you can still see what is left of their Synagogue? And did you know that it was the home of Pope Julius III? The Town Hall actually is in the Pope’s country house, a beautiful palace in Renaissance style, with formal stone façade, central court and most of all amazing Italian gardens with open view of Tuscany hills full of olive trees.

Castiglion Fiorentino is only 10 minutes away from Cortona and, although it is not so famous as the town of “Under the Tuscan Sun”, it also boasts an ancient city centre full of extraordinary architecture and artworks that prove the importance of its role in the ancient times, and shows evident traces left by World War II battles that left deep wounds in the local community. Did you know that in the XIV century its name changed three times? from Castiglion Aretino, to Castiglion Perugino, and finally Castiglion Fiorentino – and with this you understand that Florence eventually had its hands here too.

And close to this town there is a small jewel on top of a hill surrounded by olive groves and overlooking Valdichiana that is open to visits on only few dates, the Castle of Montecchio Vesponi - now a private property, it is one of the most ancient fortresses present in Valdichiana whose austere stone walls speak of times long past reminding us of Medieval life so well.

Have I stimulated your “historical and cultural appetite” ? hope so and to see you here soon, ready to explore these new Tuscany destinations with me! Read on at this link to find out about my guided tours here!