5 Towns in Tuscany To Visit

Carolina Casini 10/01/2024
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 famous Renaissance cities of Siena and Florence, but my personal favorites are the smaller towns where time seems trapped in a bygone era. One of the best parts about visiting Tuscany is the ability to explore all of the small, lesser-known, towns that are scattered throughout our rolling hills.
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 is 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 in Tuscany to visit that should be on your radar for your next trip to Tuscany.

1. Montebenichi

The first of my five favorite towns in Tuscany to visit is Montebenichi. 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.

Castelletto di Montebenichi

Castelletto di Montebenichi

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 at TuscanDream.
We have the charming 11 bedroom Villa Felciai, the lovely air conditioned 8 bedroom Villa Fabbri, and 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. This location in Tuscany is 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. Other Tuscan towns that neighbor Trequanda are 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 is full of mouth-watering restaurants and is home to some of the best truffle hunting in Tuscany.
Trequanda’s monuments that can’t be missed include the Cacciaconti Castle and the main Piazza Cacciaconti.
Trequanda, Tuscany, Italy

The Church of Saint Peter and Andrew – Trequanda, Italy

Another spot in Trequanda that one must see 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 from May to October.
Local restaurants in Trequanda include La Romota and Ristorante Conte Matto. These local restaurants are both 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.

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. It is the rumored birthplace of Amerigo Vespucci. I highly recommend adding this to your list of must-see towns in Tuscany to visit.
Small town Montefioralle in Tuscany, Italy
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 were 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.

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 Tuscan houses, and a 12th century castle (Duomo di San Cristoforo) offering a breathtaking 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.
Barga at Sunset
The area of Garfagnana itself is known for it mountainous rugged terrain, and fantastic food. Activities here are for the sporty sort, including hiking, cycling, river-rafting, to name a few. During the summer months, the village is home to a superb jazz festival.

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. Cetona is a fantastic town in Tuscany to visit and it has a wide variety of things to do within the town and nearby. This town sits 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 the title of Marquis to Chiappino Vitelli, who made the medieval fortress, la Rocca, his residence.
Magnificent view of the ancient hilltop village of Cetona, Siena
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. Located near Cetona are the Belverde caves in the Monte Cetona Natural and Archaeological Park. Cetona also serves as an ideal base for visiting the nearby towns of Pienza, Montepulciano, Chiusi (with its great Tuesday market), Arezzo and Orvieto. Trasimeno lake, near Cetona, is perfect for water sports. Take a dip in the thermal springs at Bagno Vignoni. With so much do to within and around Cetona, it’s absolutely impossible to get bored here.

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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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