The 11 Most Beautiful Towns in Tuscany

Written by Rem Malloy, since 1995 Rem has been guiding and designing trips to Italy and all of Western Europe and is considered an expert in his field for over 30 years.

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Tuscany is a region of Italy that needs no introduction. Famous for its wine, culture and scenery, it’s one of the most-visited areas of Italy and has inspired artists and writers with its stunning, natural beauty for centuries.

Besides busy cities like Florence and Siena, there are hundreds of little towns and villages scattered around the hills that are full of historic charm, unforgettable local cooking and jaw-dropping Tuscan views. One of the best ways to see the region’s authentic charm is to visit its classic hilltop towns and medieval hamlets, which are among some of the most beautiful places in Italy.

To help you decide which Tuscan towns to visit on your next trip to Italy, here is our guide to 11 of the most beautiful places to visit in Tuscany.


Montepulciano boasts beautiful views and is also one of the most famous towns in the whole region. Its notoriety comes from the local varietal of grape named used to make the award-winning Montepulciano wine, known for its rich and full-bodied flavor.

Surrounded by vineyards that produce this signature Tuscan grape, Montepulciano is a rustic and medieval town full of Renaissance architecture that gives it a peaceful and historic atmosphere. Its hilltop location means that you can admire the surrounding scenery from the town’s many terraces and squares, linked together by steep streets and lanes that open out into classic piazzas.

The journey up to Montepulciano features some of the most beautiful scenery in Tuscany, so this is a destination that should be firmly at the top of your list if you’re looking for unforgettable views. With its mix of architectural styles and gorgeous surrounding landscape, it’s a quintessential Tuscan town. 


One of the most beautiful small towns in Tuscany is San Gimignano, found close to the city of Siena in the centre of the region. With medieval walls surrounding the settlement and forests and fields outside of this, it’s a historic location that has a charming and ageless beauty.

San Gimignano is one of the most popular Tuscan towns near Florence to visit either for the day or an overnight stay. It’s best known for the fourteen distinctive towers that were originally built by wealthy families who lived in the area to display their prosperity, one of which still allows tourists to climb and admire views from 54 metres up in the air.

This ancient town is pretty small, but it is this quaint size that makes it such a picturesque part of Tuscany to visit. With markets, shops, cafes, churches and museums all found within the winding streets, this is a classic rural destination that is not to be missed.


Volterra is another of the most popular towns to visit in Tuscany near Florence, built high up in the west of the region and surrounded by a historic wall that is thought to have been built in the 13th century. With classic red-tiled roofs and plenty of medieval architecture, this is a location for fans of Italy’s ancient history as well as those who like Renaissance buildings.

There are churches, museums, galleries and an Etruscan acropolis all to be explored in Volterra, but the wide range of attractions aren’t the only thing that makes this such a busy part of the region. It’s one of the most beautiful Tuscan hilltop towns because of its vantage point and the spectacular views of the countryside that can be seen from many parts of the historic centre.

The Tuscan landscape can also be admired from outside the impressive Medici Fortress, built to protect Volterra in the 15th century and an iconic part of the town’s skyline. Ancient Roman ruins are only a short walk away, along with many remains of the town’s Etruscan heritage.


A very popular town for travellers visiting this region is Lucca, which is well-regarded as one of the most beautiful places in Tuscany. With colourful white and yellow houses, over 100 churches and architecture from almost every historic era, it’s a fantastic part of Italy to visit and experience a classic medieval town. 

Lucca is surrounded by fortified city walls that were built in the 16th century and have been maintained so that they are still standing today. You can walk the fourteen-kilometre circuit provided by the walkways on top of these walls to truly experience the town and its surrounding scenery, admiring what makes it such a beautiful location.

This is a brilliant town to visit in Tuscany for the day, as it can easily be reached by car, bus or direct train from Florence. The best way to experience Lucca however is to stay for at least one night and enjoy the local hospitality and chance to stay in one of the town’s historic buildings.


Monteriggioni is more of a village or hamlet than a town thanks to its very small size, but it’s certainly a location with a lot to offer its visitors. This beautiful hilltop settlement is full of tiny little gardens, shops, houses and piazzas that are just as pleasant to look at as the miles of surrounding Tuscan hills and forests.

The most distinctive feature of Monteriggioni is that the whole village is enclosed in historic walls that were built to protect the settlement in the 1200s when Florence and Siena were fighting to overcome the other. There are watchtowers positioned amongst the walls and that provided the ancient inhabitants with places to defend themselves and catch sight of any potential invaders, which now provide brilliant vantage points for modern-day tourists to admire the area.

It’s the rich history of Monteriggioni that makes it such an interesting place to visit, and there are a surprising amount of different things to see and do inside the citadel walls, despite its small size. You should definitely put this Tuscan village on your list of beautiful places to visit if you’re after unique historic settlements with plenty of impressive architecture.


Located in the southeastern part of Tuscany, Cortona is one of the best Tuscan towns to visit if you’re looking for a location that won’t be overrun with tourists. Its position on the edge of the region means that it isn’t as frequently visited as other popular locations, but this lack of crowds is thought by many people to make the town even more beautiful.

With views of the Chiana Valley and Lake Trasimeno, Cortona is perched 600 metres above sea level and is a quintessential hill town in Tuscany that is particularly perfect for watching the sunset. There are plenty of wonderful things to see inside the town itself, with numerous churches, museums and towers as well as lots of winding streets of historic red-roofed houses.

Cortona is best-known for its inclusion in the famous book and film Under the Tuscan Sun, as well as the delicious red wine that is produced from vineyards near the town. Many people stop off in the hilltop town on their way to or from wine tasting experiences, completing their discovery of the region with a classic local meal accompanied by Tuscan views of the hills. 


Pitigliano stands right on the border between Tuscany and Lazio, built on a rugged tuff cliff that was first chiselled by Etruscan settlers and then finished by Roman troupes. It’s one of the most beautiful Tuscan towns because of this dramatic setting and the incredible views that it enjoys of a lot of the region’s countryside.

The forests and hills surrounding Pitigliano offer some of the most interesting and beautiful terrains for walkers and hikers in the whole area, with trails carved by the original Etruscan people who first chose this location for their homes. It’s also a prime location for history fans thanks to the Jewish community that was welcomed into the town in the 14th century and left its synagogues and stories to be discovered throughout the winding streets.

If you ask for recommendations of the most beautiful towns in Italy, many people will direct you towards Pitigliano because of its breathtaking architecture and landscape. With history, culture, outdoor adventure and inspiringly gorgeous scenery, this is a Tuscan clifftop town that has more than enough to delight every visitor.


Tuscany’s Chianti region is known for its stunning vineyards and beautiful medieval buildings, so it’s no surprise that the village of Montefioralle in the area is on this list. Surrounded by groves of olives and grapes, it’s the perfect place in the Tuscan countryside to come and disconnect from the busy pace of modern life.

Montefioralle is known as one of the most beautiful villages in Italy for the simple natural beauty of its surroundings and the quaint charm of the historic buildings that are surrounded by an ancient protective wall. There are hardly any cars in the village, but exploring the streets on foot is all part of the peaceful experience you’ll discover when you visit.

There’s a popular family-run winery in Montefioralle that is an ideal place for an afternoon of wine tasting and touring the cellars filled with classic red wines such as the famous Chianti Classico. Although this is one of the smallest towns in Tuscany, the views, food, wine and atmosphere make it a must-see if you’re searching for beautiful places in the region.


Many travellers refer to Suvereto as one of the ‘most perfect medieval towns in Tuscany’ so if you’re looking for a beautiful Renaissance destination in the region, it should definitely be on your list. Found amongst the forests of the Livorno Province, it’s another Tuscan hilltop town surrounded by historic walls and filled with old stone buildings.

Suvereto is thought to have been established around 1000AD, and you do truly feel as though you are stepping back in time as you wander the streets. It’s a brilliant destination for history lovers who can visit the 10th-century Suvereto castle, a 13th-century convent and plenty of classic Italian churches.

It’s also a prime location for fans of art and culture, with galleries, craft shops and both musical and theatrical performances hosted in the town. With charming streets, alleys and buildings everywhere you turn and gorgeous sweeping views outside of the ancient town walls, Suvereto is a hidden gem in Tuscany that you won’t want to miss out on. 


Fosdinovo is often thought of as the gateway to the region of Lunigiana and enjoys a wide range of scenery that features views of the mountains, hills, forests and Tyrannian Sea. It’s a stunning hill town in Tuscany that is perfect for enjoying clear views of the countryside for miles around and enjoying the surrounding hiking and cycling trails.

The most famous feature of Fosdinovo is Malaspina Castle, built in the 12th century and still beautifully preserved. It has a fascinating past that includes inhabitation by the Malaspina Marquises and a period of being used as a prison. It is open for visitors today and includes a museum where you can find out more about the town and the castle’s past.

If you’re looking for history, drama and fantastic local food, Fosdinovo is one of the best towns to visit in Tuscany to enjoy all of these. Its hilltop location means that there are beautiful views wherever you go, and along with the impressive castle there are plenty of other historic buildings and charming examples of ancient architecture and decoration. 


The final location on our list is one of the best-kept secrets in the region and a strong contender for the most beautiful small towns in Tuscany. Barga is nestled between the Tuscan-Emilian Apennine mountains and the Apuan Alps near Lucca and has been almost entirely untouched by tourism, which is ideal for travellers that are looking for authentic beauty.

The Cathedral of San Cristoforo lies in the centre of Barga and is surrounded by simple houses painted yellow, white and peach, making this town look particularly beautiful when the sun is setting. With winding streets and alleys leading to piazzas, churches and a castle, it’s best to forget trying to use a map and just wandering freely when you visit.

The lack of tourists in Barga means that you’ll have to brush up on your Italian before arriving, but it’s worth it for the peaceful atmosphere, friendly locals and stunning scenery that you’ll enjoy during your time in this Tuscan town.

For more information about visiting towns in Tuscany and to find out about how we can plan your dream tour around this famous region, get in touch with our team and speak to an Italian vacation expert.

About the Author

Rem Malloy started Italy4real back in 1995 with his mother, Deborah de Maio.

He specialises in Italian tours as well as customised tours to France, England, Ireland, Germany, Switzerland, Greece and Spain. He was also featured in the Travel Channel show Mysteries at The Museum in 2016.

Rem has family in Italy and his mothers home town is Cava di Terrani, near the Amalfi Coast. The family has a street named after them in Sorrento, Via Luigi de Maio; a relative who was mayor of Sorrento.

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