10 Pretty Small Towns in Tuscany

Tuscan towns are well-known for being among the most attractive places in Italy, and no holiday to Italy is complete without seeing at least a few of them.

There are so many charming little towns in Tuscany that it would be hard to compile a list of them all.

Also, it wouldn’t be very beneficial if you were trying to decide which Tuscany towns to visit first!

I choose to focus on a hand-picked selection of the most stunning Tuscany towns that you should aim to include in your Tuscany itinerary for the ultimate experience rather than compiling a big list of charming little towns in Tuscany.

I hope you find it interesting!

Pretty Small Towns in Tuscany 2024

1. Florence

Florence, the capital of Tuscany, is well known for its historical influence on Italian fashion, lifestyle, and architecture.

Two notable locations are the Neptune Fountain and the Galleria dell’Accademia, which houses Michelangelo’s David sculpture.

The centuries-old Ponte Vecchio Bridge highlights the Arno River, lined with rows of stores and vendors.

The Santa Maria del Fiore (or Duomo) Cathedral, with its 15th-century terracotta dome created by Filippo Brunelleschi, is the dominant structure in this city center. Enter to view the Last Judgment paintings by Giorgio Vasari; entry is free.

2. San Gimignano

My list includes San Gimignano because of its stunning appearance. 13th-century medieval walls surround the town and is teeming with examples of medieval architecture.

This town, often known as the “Town of Fine Towers,” is an excellent choice. The village is so remarkable that UNESCO has designated it as a World Heritage Site.

You may spend half a day seeing this historic town, but a longer stay is usually preferable if you have more time.

The great plaza, Piazza del Duomo, is encircled by the towers that give San Gimignano its name. San Gimignano features two principal squares.

One of the many tiny cafés encircling the plaza is a great place to grab coffee and sit outside. The second main plaza in San Gimignano, Piazza Della Cisterna, is shaped like an odd triangle with structures from the 13th century.

3. Cortona

Cortona is a classic Etruscan walled town in the province of Arezzo in southern Tuscany. Its 600 meters above sea level provides breathtaking views of Lake Trasimeno and the surrounding region.

The town may be small, but it has plenty of appealing places to see, such as the Diocesan Museum, which has a stunning panel painting by Beato Angelico, and the MAEC, which has interesting artifacts from nearby archeological sites.

Some lovely churches are scattered throughout the town, such as the Santa Margherita Sanctuary, which is definitely worth seeing.

It might be familiar to you from the movie and book Under the Tuscan Sun. There are plenty of locations in this area, which is well-known for its red wine, where you can unwind and have a drink after a long day.

4. Pienza

Pienza is a small Tuscan town that is unique because it had significant improvements in the fifteenth century that transformed it from an ordinary community into the ideal “Renaissance utopian town”!

Pope Pius II, whose real name is Enea Silvio Piccolomini, is the most well-known son of Pienza and the driving force for this change.

The Humanist Pope had a very clear idea of the ideal urban setting. As a result, Tuscany has some of the most exquisite towns.

I must say Pienza has an amazing center plaza, a magnificent promenade along the bastions with breathtaking views over the surrounding hills, and a plethora of charming streets that are well-maintained by the city’s contemporary residents.

Pienza, the Renaissance dream town and pinnacle of “beautiful,” has been recognized as a UNESCO World Heritage Site since 1996.

5. Lucca

Beautifully maintained Renaissance walls from the sixteenth century enclose the little Tuscan town of Lucca. You may travel the 4 km length of the ancient city walls on foot or by bicycle. The entire town is seen from the panoramic walkway.

Known as “the city of 100 churches,” San Michele al Foro, San Martino, and San Frediano Basilica are a few of the city’s most well-known cathedrals.

Other noteworthy locations include the Piazza dell’Anfiteatro amphitheater, the Museum of Villa Mansi, the Guinigi Tower, and the Torre delle Ore.

6. Montepulciano

Montepulciano, an aesthetic paradise just outside of Siena, is a visual feast. This medieval town is lined with Renaissance architecture, which was brought about in the sixteenth century by the wealthy Medici family.

Its architecture is so authentic that no significant construction has taken place here since 1580.

The Piazza Grande is the center of town, where you may savor a glass of the region’s Nobile wine and take in the Duomo’s ramshackle brick façade.

A plethora of cellars and tastings await you surrounding the plaza, should that first glass not satisfy the taste buds.

7. Siena

Tuscany’s southern city of Siena is recognized as a UNESCO World Heritage Site. The antique old town, with its narrow cobblestone alleyways and terracotta rooftops, is home to the massive Basilica of San Domenico, Palazzo Pubblico, Palazzo Salimbeni, and the Cathedral of Siena.

There are several museums with exhibits that transport you back to the Renaissance period and lovely courtyards that make for great places to have picnics.

Because Siena is tiny, it is simple to visit all of its ancient sights in a single day. Palio di Siena is a historical horse racing event in the town’s Piazza del Campo area twice a year, generally in July and August.

8. Pitigliano

It’s known as “Little Jerusalem” in Italy. Pitigliano, an ancient village in Tuscany, Italy, is a breathtaking site situated above a stony cliff.

Most of its structures and towers were constructed from the same cliff granite, among the primary attractions of Pitigliano, which has a long-standing Jewish population.

There are a number of historic caverns dug into the cliffside that were formerly thought to have been used as secret synagogues during the persecution by the Romans.

You can visit the historic Orsini Fortress and the old Santi Pietro e Paolo Cathedral.

9. Barga

Beneath the majestic Pania Della Croce, Barga extends over the Tuscan landscape. The town’s majestic Duomo and the ancient Renaissance manors’ beige and yellow walls stand out sharply against the surrounding alpine slopes.

The alleys and piazzas are full of rustic beauty, and the town’s annual Sagra del Pesce e palate exudes a curiously Scottish charm with its retro red phone boxes dotted around the block.

10. Monteriggioni

One of Tuscany’s best-preserved wall castles is in Monteriggioni’s ancient town. Monteriggioni is a bustling town square with tall watchtowers and cobblestone lanes and only a short drive from Siena.

Situated on a hill, you may access the town’s main Piazza di Roma by going via either the Franca or Romea gates.

Every July, Monteriggioni has its Medieval Festival. During one of Tuscany’s most well-known celebrations, crowds of people dressed in medieval garb perform falconry feats and eat customary Roman fare in the streets.

Conclusion

Tuscany is full of gorgeous towns, as you already know. I’ve covered the finest of the best, including a few Tuscan towns. Which of these stunning Tuscany towns is your favorite place to visit?

Once you’ve seen the towns of Tuscany, don’t forget to see the capital city of Florence. One of the finest things to do in Italy is to spend a day in Florence, which offers an abundance of activities. Enjoy your wonderful trip to Tuscany.