Last Updated on October 25, 2023 by Ingrid & Alex

While it is hard to choose, Tuscany might be one of Italy’s most popular and beautiful regions, and for good reason. Small villages scattered around hills and valleys, the home of one of the best wines, driving along vineyards and carefully alined cypress trees and olive trees, luxury historic villas, and mouthwatering food. 

But which are the prettiest towns in Tuscany you should consider stopping in? I’ve gathered here a list of places recommended by travel bloggers, based on their experiences, and the places they fell in love with. So you can easily pick and choose which Tuscany village to visit!

So that you can plan your trip accordingly, no matter if you only spend one week, 10 days in Italy, or even more.

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Important things to know for when you visit Tuscany

Where to fly into for visiting Tuscany?

While there are many options for getting to Tuscany, these are the 2 most important airports in the region, that will set you close to the Tuscan villages you’ll visit: Florence and Pisa

The Pisa Airport, Galileo Galilei, is larger than the one in Florence and is serviced by both low-cost and line companies such as British Airways, Lufthansa, Turkish Airlines, or Qatar. 

Check the best flights from your location here Kiwi.com!

How to travel around Tuscany

While Northern Italy has a great infrastructure and public transportation, the easiest way to get to all the beautiful towns in Tuscany is by renting a car. 

Just imagine yourself driving around in a small Fiat 500, passing by olive tree orchards and historical villas!

Discover Cars is my go-to tool for renting cars. It is a great aggregator that will help you find and book the best option for renting a car during your trip, helping you save up to 70% on your car rental. They have a pretty good Cancellation policy that would give you options in case your flight or travel plans change.

Get your offers here!

How many days to spend exploring Tuscany?

That depends a lot on so many factors.

From your travel style, to how much time you have to enjoy your Florence itinerary, to what budget you have allocated for this trip, 

You can easily spend a long weekend wandering around the winding roads of Tuscany, but you can also come here for a few months without ever getting bored!

The prettiest towns in Tuscany you must see

Siena

prettiest towns in Tuscany

By Inguaribileviaggiatore.it

Siena is one of the primary and most visited cities in Tuscany, known for its enormous historical, artistic, and landscape heritage and the famous Palio.

A full day in Siena is certainly not enough to experience the city in all its nuances and to visit and see all the heritage it offers, so it is better to spend two days in Siena.

The dominant color in Siena is the red of the Tuscan terracotta, of the houses and roofs, which makes the prestigious marble buildings stand out even more; above all, the black and white of the Cathedral, which stands out imperiously and visible from most of the city. But also the Gothic-style Palazzo Salimbeni is made of stone, in the beautiful Piazza Salimbeni.

However, the beating heart of the city is Piazza del Campo, where the three hills join.

Among the things to see in Siena is the beautiful Gaia fountain. The work takes this name because of a great party organized by the Sienese. The Gaia fountain was the first to allow drinking water up to Piazza del Campo, which is probably not very simple for that time.

The Piccolomini library was built in 1492 to house the books of Pope Pius II and decorated in the early 1500s by Pinturicchio and aides, including Raphael. The frescoes tell of the life of Enea Silvio Piccolomini, who became Pope with the name of Pius II.

When you enter this library, you don’t know where to look, if at the books, the ceiling, the frescoes it’s a jewel!

The best tours in Siena:

Monteriggioni

Monteriggioni_villages in Tuscany

By Travel with the crew

When you are traveling through Florence you must make sure to stop to see Monteriggioni. This charming Tuscan town is home to many historical monuments. Monteriggioni is located on a hilltop and had its “golden age” between the 14th and 15th centuries.

It started life as a fortified castle and became a town in 1630. It was also the stronghold for many noble families leaving an important heritage of art and architecture.

Although the town of Monteriggioni is quite small, it is iconic due to its unique fortress walls. The town is surrounded by a high, 5m thick wall that was built in the Middle Ages.

The main attraction within Monteriggioni is its castle. The castle was built between the 13th and 15th centuries and today hosts many cultural events such as concerts and festivals. The castle has 14 unique towers that give you an unimpeded view of the town and surrounding countryside.

Besides the Castle, there are some other places worth visiting while in Monteriggioni; Santa Maria and Piazza de Roma.

If you are visiting during July, you can see the Medieval Festival that takes place at Monteriggioni each year. Recreations of life during the Middle Ages, craftsmen, soldiers, and more give you a peek at life long ago.

The best way to get to Monteriggioni is by car as it is direct and parking is easy. You can also take the bus from Florence but the ride is a little longer as it stops along the way.

The closest airports are Pisa and Florence Airports

Best tours that will take you to Monteriggioni:

Lucca

Lucca cathedral

By Brainy Backpackers

Lucca is one of the underrated, yet impressive destinations in Tuscany you need to visit whether it’s a day trip from Pisa or Florence or if you’re on a Tuscany road trip visiting more of this amazing region in Italy.

Among the main attractions are the towers Torre Delle Ore and the Guinigi Tower for views of the old town. But you should also head to the cathedral, decorated with unique columns. But Lucca might be the most known for San Michele in Foro and the basilica of San Fernando.

Make sure you head to Piazza dell’Anfiteatro to eat pizza or at least for a drink. The unique square is built on top of the old amphitheater and the buildings outline the walls that are buried underground, forming an oval circle of pastel-colored houses.

While you can see most of Lucca’s attractions in a day, it is worth spending a couple of days in this charming town to get a good feel of it. There are public parking lots outside the town walls, but it is not allowed to drive inside the old town for unauthorized vehicles.

If you don’t drive, you can get to Lucca by bus or train both from Florence in less than 2 hours and from Pisa in only 15-20 minutes.

Best tours in and from Lucca:

San Gimignano

San Gimignano, Italy

By PlacesofJuma

One of the most beautiful towns to visit in Tuscany is certainly San Gimignano. This charming place is located in hilly Tuscany, 50 kilometers south of Florence, and is for many a must-see on any round trip. The best way to get there is by car, or you can book an excursion. It is also worth spending 2-3 days in this area to explore the surrounding destinations (e.g. Chianti, Siena, and Monteriggioni).

San Gimignano is often called the “Medieval Manhattan” and the old town is listed as a UNESCO World Heritage Site. In particular, the many tall medieval towers form an imposing backdrop. Some of these towers are up to 50 meters high and 14 of the former 72 are still well preserved today. Because of its good state of preservation, the entire town center of San Gimignano has been included in the UNESCO World Heritage List.

A walk through the old stone streets of the historic old town is truly romantic. At almost every corner you will discover a monument, a sight, and also find countless opportunities for beautiful photos. Don’t forget to try the ice cream at Gelateria Dondoli in the main square, Piazza Della Cisterna. It has been voted ice cream world champion twice!

If you want to spend a holiday here, we recommend the Castello di Fulignano – a beautiful castle with flats, a huge pool, and a magnificent panoramic view over the Tuscan hills.

Best tours in San Gimignano:

Panzano

Panzano hills Tuscany

By May Cause Wanderlust

Deep in the rolling hills of the Chianti region of Tuscany is a small town called Panzano. Its cluster of pretty red-roofed houses is surrounded by picturesque vineyards punctuated with poplar trees. It is charming and peaceful and idyllic, like many other towns in Tuscany. However, what sets Panzano apart is a complex of restaurants from a legendary chef, Dario Cecchini, known affectionately as the Butcher of Panzano.

If you watch Chef’s Table on Netflix you may have heard Dario’s story. He grew up loving animals and wanted to be a veterinarian, but was obligated to take on the family’s butchery business when his father died. He felt very conflicted between his desire to help animals and his desire to look after his family. After some time, he found a way to resolve this conflict: to respect the gift of the animal and to make use of every part of its body when it dies. His restaurants, which include Solociccia, right next to his butcher’s shop, practice nose-to-tail eating. His set menus include all parts of a cow, transformed into creative dishes and served in one sitting on communal tables, often to great fanfare and clapping, in honor of the food. The celebratory atmosphere is amazing!

It is definitely worth spending at least a day in Panzano, which is about an hour by car from Florence. If you don’t eat meat, skip Dario’s restaurants, but don’t skip the Il Palagio di Panzano wine shop opposite – they offer tastings of local wines and have glorious views over the rolling Tuscan hills.

Volterra

Volterra_towns in Tuscany

By Tourist to travellers

The old historic town in Tuscany is known for its numerous attractions and countless archaeological sites. Not only is this beautiful town a historic center but it is also popularly known as the “City of Alabaster” because of the alabaster processing that takes place here. Volterra is also known for its rich Etruscan heritage that dates back to the 4th century B.C. Tourists can come and soak in the history that this town has to offer.

Things to do in Volterra

Piazza Dei Priori – One of the must-see places in Volterra. It’s the main square of the medieval town. Enjoy a cup of coffee in one of the cafes and enjoy the view.

Etruscan Museum – This is one of the oldest museums in Europe. Beautiful ceramics and urns are on display here.

Palazzo Incontri Viti – A museum that provides an insight into the lives of the royals of Volterra. It contains the relics of the Viti family.

Roman Theatre – One of the most important archeological sites of Volterra.

How to Reach Volterra

The closest airport to Volterra is in Florence & Pisa. One can either rent a car or catch a bus or train to Volterra from the airport. One would be spending approx. 3 hours on the road to travel from Florence to Volterra.

Go on a tour:

Pienza

Pienza Tuscany

By Italy Foodie

There are so many wonderful towns to see in Tuscany, Italy, and Pienza is one of the best.

Located on a hill overlooking the stunning Val d’Orcia, Pienza is 117km (73 miles) south of Florence. It’s an easy and scenic one-and-a-half-hour drive, or if you’re staying in nearby Montepulciano, it’s just 20 minutes away and well worth the beautiful drive.

In 1996, Pienza was named a UNESCO World Heritage Site. Considered “the ideal city of the Renaissance” as the birthplace of Pope Pius II, the Pope had the town completely remodeled to reflect the height of the Italian Renaissance.

To see this amazing architecture, visitors should visit Piazza Pio II, the central town square. Here you will find the Papal Palace, town hall, the ‘well of the dogs’, and the Cathedral of the Assumption, completed in 1426, along with its octagonal bell tower.

One of the most compelling reasons to visit Pienza is the traditional Tuscan food and excellent wines. The village is at the heart of an area that has drawn foodies and wine lovers into the know for years. A must-try is Pecorino di Pienza, a hard cheese made from sheep’s milk that this region of Tuscany is famous for.

If you have the time, plan ahead and take advantage of a food and wine tour. Pienza is a great day trip to try wines and have an incredible dinner.

Tours that will take you to Pienza, and useful entry tickets:

Montecatini Terme

Montecatini Terme Tuscany

By Dymabroad

One of the best towns to see in Tuscany is Montecatini Terme. It is a small town in between Florence and Pisa. It is a lovely town with some interesting things to do and see.

Besides that, its central location makes it perfect as a base for exploring more of Tuscany.

One of the best things to see in Montecatini Terme and the sight for which it is known is the Parco Delle Terme. This is a spa complex that has beautiful architecture. Another one of the best things to do in Montecatini Terme is riding the funicular to the top of a hill where you can find Montecatini Alto.

From there, you have a wonderful view of the town. Besides that, another top sight in the town is the MO. C. A, Montecatini Contemporary Art museum. This is an interesting museum with modern art that is housed in a historical building.

Getting to Montecatini Terme is easy as there is a train station that connects the town to other places in Italy. Besides that, the town can be reached from other cities by car in a short amount of time. From Florence, it takes about 45 minutes by car to reach the town.

Get your entry ticket to the Thermal Pool!

Montepulciano

Montepulciano Tuscany

By Merryl’s travel and tricks

Montepulciano is an ancient countryside town in Tuscany known for the fine red wine and the beautiful countryside views. It can be reached easily by road from Florence or Rome in about 1.5-2 hours. It is definitely the perfect town to visit for anyone who loves authentic food, amazing local wine, and wants to experience the real Tuscan countryside.

The ancient city center of Montepulciano is filled with pretty squares, renaissance palaces, ancient churches, charming corners, and unmatched views of Val d’Orcia and Val di Chiana. Piazza Grande is the main square in the town and has plenty of bars dotted around it for a quick coffee stop. The town is also known for the typical red Montepulciano wine. You will find little cantinas dotted through the city offering free product tastings.

For food lovers, this town has plenty to offer. From pasta to steak and cold cuts and cheese, everything is fresh and locally produced. Osteria Acquacheta is the place to go for some local pasta and the famous Fiorentina steak. Make sure to try the Pici alla Cinghiale, a pasta with wild boar meat sauce, or the Pici all’Aglione for vegetarians. You can also try a variety of local cheeses and salamis at the cantinas in the town.

Here are the most popular tours you should take in Montepulciano: 

Pitigliano

Pitigliano

By Travel Connect Experience 

Pitigliano is a small town in southern Tuscany, a few kilometers from the border with Lazio. One of the most picturesque medieval towns in Italy, it is part of a geological, historical, and archaeological area called “Tuscia”. The towns of Tuscia stand on spurs of tufa rock surrounded by streams and thick, lush vegetation. In fact, from the small terraces at the edge of Pitigliano, you can enjoy a breathtaking view of the gorges that surround it.

But the landscape is not the only strong point of Pitigliano, which is rich in historical monuments.

In the first half of the 17th century, the noble Medici family of Florence built a monumental aqueduct with 15 arches to supply the town with water. The aqueduct culminates with the ” Fountain of the 7 Spouts” which is decorated with bas-reliefs of different historical periods.

Along the main street “Via Roma”, there are souvenir stores and artists’ workshops. Going all the way, you get to a small piazza dominated by the facade of the Cathedral of Saints Peter and Paul, dating back to the 13th century but then renovated. On one side of the square, from an arcade, you can access a stone staircase connected to the alley below, where there is the Jewish quarter, one of the oldest in Europe, with the Synagogue and a museum.

It takes about 3 hours to explore all the alleys, squares, and hidden viewpoints of Pitigliano.
The town is also immersed in the archaeological area “Cities of Tuff”, which includes miles of nature trails through the fascinating streets carved into the rock by the ancient Etruscans, in pre-Roman times.

How to get there:
Take a train to Viterbo or Grosseto and then a bus to Pitigliano.

Pisa

Pisa

By The Purposely Lost

Although most visitors only spend one day in Pisa, it’s one of the best towns in Tuscany. The city’s most iconic landmark is the Leaning Tower of Pisa. The magnificent edifice was constructed starting in the 12th century, but by the time the second story was started, it was already leaning.

Although some mistake it for a lookout, the Tower actually operated as the bell tower for the adjacent Cattedrale di Pisa. In addition to the Tower and Cathedral, there is a baptistry and a cemetery.

Because most tourists only come to Pisa to see the Tower, the remainder of the city is rather quiet. Walking along the Arno River, which runs directly through the city, and its side streets will give you a good sense of the local culture. The numerous distinct town squares are surrounded by fantastic coffee shops and small merchants.

Pisa also boasts a lovely shoreline, Marina di Pisa, despite the fact that the major city center is inland from the coast. Pisa is a fantastic city to visit while in Tuscany, with everything from huge, famous sites to smaller, local neighborhoods and a gorgeous beach.

Tours and tickets you must have when visiting Pisa:

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The prettiest towns in Tuscany you must see


2 responses to “The prettiest towns in Tuscany you must see”

  1. […] your home base in Florence, or choose one of the smaller pretty towns tucked away in the Italian […]

  2. […] trip itinerary isn’t simple, but it’s well worth the effort. In fact, with endless little cute towns in Tuscany as well as bigger cities that are home to hidden gems, staying a few days are sometimes not […]

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