There is a list of the official prettiest towns of Italy, I Borghi più Belli d'Italia, a title that is formally bestowed on the cleanest, best-preserved, most charming, and most quaint towns and villages all across the country. Tuscany, known to be an especially pretty region, is home to many of the big-hitters on this list with twenty-nine entries in total hailing from Tuscany alone. It is, therefore, quite hard to name one example as the uncontested prettiest town in Tuscany. In fact, depending on your perspective and your tastes, there are many excellent contenders with different selling points and atmospheres. If you are thinking of booking one of our astounding villas in Tuscany and you were dreaming of seeing the most charming and picturesque parts of this famously beautiful place then here are a list of just some of those contenders and some of our favourite towns to visit in Tuscany...
1. Anghiari
Starting off in the hilltop town of Anghiari, in the Province of Arezzo, surrounded by its old walls and retaining a strong and charming medieval character. Looking like something from a fairy tale, it rises atop lush green surroundings, a few kilometres from the town of Arezzo itself. Made famous by a lost painting by Leonardo da Vinci, Anghiari is full of character and boasts a beautiful and preserved historic core, architectural gems, castles and fortresses, little museums, and amazing views over the Tuscan countryside. The town also hosts an annual recreation in costume of the battle da Vinci famously painted, a renowned craft market each spring, theatrical events, and an excellent food festival each November. A wonderful spot for those who love places that feel as though time as stopped, for anyone looking to shop for antiques, and to eat well, it is an ideal day-trip destination if you book a vacation rental in Tuscany.
2. Cetona
Another gorgeous and historic hilltop town, Cetona is a preserved gem and an archaeological site set on the slopes of a mountain of the same name with olive and cypress trees all around in the Sienese Valdichiana. With charming streets that spiral up towards the citadel, Cetona boasts a pretty centre made up of architectural wonders, a fascinating museum of prehistory, a contemporary art gallery, and a whole host of interesting events throughout the year. Among the events in this calendar there is Cetona In Fiore, which turns the whole town into one great garden each spring for three days and sees florists and artists gather to create amazing displays, trails through the town, and various attractions and gatherings. Fairs, an olive oil festival, a summer schedule of cultural offerings (including cinema events, concerts, and exhibitions), traditional celebrations, and art and foodie festivals also take place throughout the year. Plus, those leafy slopes around town are popular for hiking and produce delicious things to eat and drink. So, for hikers, foodies, and art-lovers, Cetona is a great place to spend a day on holiday in Tuscany.
3. Montaione
Located in the heart of Tuscany, in the middle of a triangle between Florence, Siena, and Pisa, Montaione is perched high on a lush hill with sweeping views across the gorgeous surrounding countryside. While little remains of the old town walls, the centre is incredibly well-maintained and features cobblestone streets, beautiful old churches and palaces, and various spots to take in the most incredible panoramas across the lush scenery all around. Known for, “green tourism,” the peaceful and lovely landscape around the town and the rich agricultural output means that this is a place to take things slow, breathe in fresh air, enjoy beauty, and eat well. In the summer, you can attend a variety of events from jazz concerts to craft markets to dinner in the town square and, come autumn, you can sample the renowned and prized truffles found in the forests around town or attend the truffle festival that takes place each October. For those looking to get away from it all and slow things down on vacation in Tuscany, it is ideal!
4. Porto Ercole
Heading now to the Tuscan Coast, we have the beautiful seaside town of Porto Ercole, which combines the preserved historic charm seen in the other towns on this list with the gorgeous surroundings and sea views of its location. With the striking Forte Filippo, an architectural gem and unique fortress, looking down over the lovely natural bay that is full of bobbing boats, the excellent beaches, and the historic centre with its old walls and gates and little cobbled streets, it is a beyond picturesque gem. In addition, it is a place where you can enjoy all sorts of outdoor pursuits on land and in the water from hiking to sailing, an annual pirate festival, a July celebration with food and fire-eaters, a procession at sea each June, and a living Nativity scene each Christmas, as well as a host of seafood dishes with the incredible local white wine, Ansonica. So, enjoy the beauty of a typically Tuscan town and the delights of being by the sea in gorgeous Porto Ercole by booking a villa on the Tuscan Coast.
Don’t simply come and just enjoy a holiday in Tuscany but come and see the most beautiful towns in the region with your own eyes and put a dent in the list of I Borghi più Belli d'Italia on your next getaway!
