All of Tuscany is dreamy, so choosing ten magical towns from the entire region is an arduous task. These are all places worth taking the time to visit slowly, and enjoying their hidden charms. Let yourself get lost in the narrow streets of the town, walk among ancient buildings and enjoy the unspoiled landscapes. Discover the enchantment of the past. This is a personal list – please leave us your opinions in the comment space and let us know which ones are your favorites!
1 – Pitigliano, Grosseto – A town carved out of tuff – both mysterious and fascinating. One of the most interesting places in Maremma, and maybe all of Tuscany. Stay until evening because nighttime is strangely wonderful here.
2 – San Gimignano, Siena – This enchanting city of towers is one of Unesco’s World Heritage sites. There used to be 72 towers but now only 13 remain, giving their special character to this little jewel of a city in the province of Siena.
3 – Montepulciano, Siena – If you’re looking for the classic Tuscan hill town with beautiful fields and vineyards, this is it. Situated at the intersection of two valleys, this beautiful town looks like the natural continuation of the hillside on which it was built. If you love good food and wine, be sure to visit Montepulciano!
4 – Volterra, Pisa – A typically medieval city but with many Etruscan characteristics, this is a unique place. Its austerity is puzzling, and the best way to see it is by taking long walks to discover its hidden areas. 5 – Pienza, Siena – The ideal city of Pope Pio II was built in only three years and celebrates the principles of Italian Renaissance. Perfectly beautiful. Don’t miss Pienza. 6 – Montecarlo, Lucca – A tiny town hidden away in the hills of Lucca. It seems to have appeared out of a children’s book, with its well-preserved town and the stunning natural landscapes.7 – Buonconvento, Siena – Situated in the area known as the Crete Senesi – an ocean of hills that make up a starkly harmonious landscape – this small town is utterly charming. Surrounded by brick walls, it is a destination in the Val d’Orcia that shouldn’t be missed.
8 – Cortona, Arezzo – Inspiration for the novel “Under the Tuscan Sun”, by Frances Mayes, which then became a film by Audrey Wells. An amazing place with an unspoiled landscape and a slow, easy rhythm of life. The lifestyle seen in the film can be witnessed on the small streets with its medieval palazzi, still inhabited by artisans, and trattorias with traditional menus.
9 – Castelnuovo Berardenga, Siena – Nestled among the rich hills of Chianti, this town is a perfect example of Medieval architecture, with amazing churches, monasteries, castles and villas.
10 – Castagneto Carducci, Livorno – At the heart of the Etruscan coast lies Castagneto Carducci, an amazing corner of Tuscany which is constantly recognized on both a national and international level for its extraordinary beauty. Don’t miss a visit to Bolgheri with its fantastic boulevard of cypress trees.

























Love my wonderful Volterra <3 and love Bolgheri more than Castagneto Carducci…
I love Tuscany, Its little towns are always breathtaking and there are so many little places to discover…. How about wine tastings off the beaten path around there?
So many more places to visit in Italy! Beautiful!
Stayed in Lago di Trasimeno, Umbria but did trips to Sienna, Cortona, San Gimignano, Pienza, and wine tasted in Montepulciano. Tuscany is wonderful!
I love Pienza, Monterigionni, San Gimignano, Fiesole, Firenze, Greve in Chianti, Siena, Lucca and every other place we visited in Tuscany last July! Would love to see Cortona, Montepulciano, Volterra and many other towns next time.
I’m in love with Siena! One of the most beautiful cities I’ve ever seen.
I believe you when you said that was an arduous task choosing ten magical towns of Tuscany but congratulations, interesting choices!
I’ve been to 6 of the towns and I agree that they are magical! genia
j’aime la Toscane, ma préférence va à Sienne si belle et qui a gardé son cachet médiéval, mais j’aime aussi Lucca l’amphitéatro et la promenade sur les remparts, Castellina in Chianti, Monterrigiano,Volterra,tous ces paysages magnifiques et bien sûr Florence, Fiésole…c’est pour ça que j’y retourne tous les ans.
Anghiari in east towards Umbria is very picturesque and well worth a visit too
I propose also Castiglione della Pescaia as magical town!!