5 Small Towns In Tuscany That You Probably Never Heard Of (But you should!)

Carolina Casini 04/01/2016
The best part of life in Tuscany is discovering just how dynamic this central Italian region really is – it continues to amaze me, even after years of living here.  Tuscany encompasses a beautiful and diverse natural landscape with numerous UNESCO World Heritage sights. Many travelers are only aware of the Renaissance cities of Siena and Florence, but my personal favorites are the smaller towns where time seems trapped in a bygone era. Imagine tiny cobble-stoned streets where a three-wheeled car can barely pass and curious older ladies are  gossiping on stone benches while the tiniest aroma of roasted meats wafts through the entryways of small doorways. The simplicity of these villages are the reason that so many of us long to visit and make this area our home, if even for a short time. Here is a list of five towns that most have never heard of but definitely should be on your radar for 2016.
A tiny castle town in the Valdambra region, only 20 minutes northeast of Siena and an hour south from Florence, Montebenichi

is a place where one can truly unwind in this hidden gem of a village thanks to its proximity to three fabulous villas that we offer for rent, the charming 11 bedroom Villa Felciai, and the lovely air conditioned 8 bedroom Villa Fabbri  – as well as the gorgeous, five bedroom air conditioned Molino del Chianti. The two closest towns are Ambra and Bucine (which has a train station). It is also possible to stay at the stunning ancient 12th century ‘Castelletto di Montebenichi’ where owners Marco and Arnoldo have a personal art collection, well-worth a visit. For nibbles, we suggest Osteria l’Orciaia for lovely Tuscan fare like ribollita and thick pici pasta.  Easy day-trips include Montalcino, Urbino, Greve, Gaiole or visit one of the many nearby premium wineries and vineyards.

2. Trequanda
Trequanda is another charming town you probably haven’t heard of, in the province of Siena nearby Asciano, Pienza, Rapolano Terme, San Giovanni d’Asso, Sinalunga and Torrita di Siena. The town has several panoramic points from which you can enjoy a breathtaking view of the surrounding countryside. Trequanda’s monuments that can’t be miss include the Cacciaconti Castle and the main Piazza Cacciaconti. Also well worth a visit is the church of Saint Peter and Andrew, a Gothic-Romanesque beauty built in the 13th century with the interesting architecture of the municipal palace. The nature train also passes through here every Sunday May to October. Local restaurants include La Romota, Ristorante Conte Matto both spots are ideal for simply Tuscan traditional dishes.  There are some great nearby accommodations including  TuscanDream’s fabulous 10 bedroom 17th century Villa Boscarello, a vineyard estate which sleeps up to 22 people. It is perfect for family vacations or elegant Tuscan wedding parties.
Church in Trequanda - trequanda-tuscany-toscana

Village of Trequanda – church

3. Montefioralle 
Who would have known that such a jewel  could be just a mile west from the famous Greve In Chianti. This well-preserved medieval town that was once the stronghold of the Greve valley is located in the heart of Tuscan Chianti wine country and is the rumored birthplace of Amerigo Vespucci.  I only recently stumbled upon this place full of stone houses with doorways lovingly kept-up with plenty of plants and sweeping views of the countryside. It used to go by the name ‘Monteficalle’ for the fig trees that once abundantly grew around the castle and mentioned in a poem by the famous Bocaccio. This is the ideal town to explore wineries and local hearty cuisine,.  We recommend coming for the feast day of St. Joseph in mid-March when the town people fill the street for freshly-made ‘fritelle’ (sweet rice fritters). Before heading to Greve, stop at the excellent osteria (Taverna del Guerrino) inside the town’s walls.

Aereal View of Montefioralle

4. Barga (Garfagnana) 
You might have heard of Lucca, but don’t miss this medieval hilltop town in the Garfagnana area with its maze of cobble-stoned streets, pretty houses and a 12th century castle (Duomo di San Cristoforo) offering a panoramic view. Its much less touristy than other places in Tuscany and the atmosphere is deliciously sleepy and laid back. The views here offer a green window into the Serchio valley and Apuan Alps.
The area of Garfagnana itself is known for it mountainous rugged terrain, and fantastic food. Activities here are for the sporty sort, hiking, cycling, river-rafting to name a few. During the summer months, the village is home to a superb jazz festival.
Village of Barga

Village of Barga, Lucca Province

5. Cetona
Not to be confused with ‘Under the Tuscan Sun’s’ Cortona, Cetona oozes charm on the border of Umbria and Tuscany in a very strategic location. Sitting pretty, perched on a hill overlooking the valley of cypress and pine trees. After passing through the hands of many powerful nearby factions, in 1556, Cosimo I de’ Medici who was the Grand Duke of Tuscany granted Cetona and the title of Marquis to Chiappino Vitelli, who made the medieval fortress, la Rocca, his residence.
Start from Piazza Garibaldi and stop at the Church of Sant’Angelo where you can spot a special wooden statue of the Madonna and Child before heading to the Museo Civico per la Preistoria del Monte Cetona. Nearby Cetona are the Belverde caves in the Monte Cetona Natural and Archaeological Park. Plus it is an ideal base for visiting the nearby towns of Pienza, Montepulciano, Chiusi (with its great Tuesday market), Arezzo and Orvieto. Perfect also for water sports at the nearby Trasimeno lake, or a dip in the thermal springs at Bagno Vignoni.  Its absolutely impossible to get bored here!

Village of Cetona, Tuscany

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  • Fred Schumpert
    11th January 2016 at 2:52 pm

    Thanks for your post. The Tuscan region is one of our favorites for return visits in Italy since I represent a manufacturing company in Veneto (near Cittadella, and Padua). We have stayed in San Gimignano several times and visited nearby Siena, Montepulciano, Montalcino, Cortona, and the Chianti Road attractions, etc.; along with weekend stay at the Renaissance IL Ciocco Resort, near Barga, and visited nearby Barga, Gallicano, Lucca and Castelnuovo. We most often take a train from Padua, or Venice, to Florence and then hire a car to drive through Tuscan area.

    • 20th January 2016 at 1:02 pm

      Hello Fred, thank you for taking the time to comment. There are truly so many special spots in Tuscany, it’s hard to pick between them!


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