Last Updated on 5th October 2023 by Sophie Nadeau
From tiny little medieval settlements tucked high on hilltops to busy modern metropolises where the hint of history is never too far away, there’s no shortage of stunning settlements to visit next time you’re in the Tuscan area of Italy. Here’s your ultimate guide to the most beautiful cities, villages, and towns in Tuscany you simply must visit on your next Italian adventure!
Known in Italian as ‘Toscano,’ Tuscany is to be found in the cental-western part of the boot-shaped country and covers an area of about 23,000 square kilometres.
Owing to its extensive wine production, not to mention that the Tuscany capital is Florence, one of the most vibrant and beautiful cities in Europe, Tuscany offers many adventures to be had for every kind of visitor.
For the ultimate guide to the best activities and things to do in the beautiful region, check out our Tuscany bucket list guide. For those looking to enjoy a sojourn in the region, be sure to check out our suggested itinerary for one week in Tuscany.
If you’re looking for even more inspiration about the boot-shaped country, then be sure to check out our best travel quotes about Italy. And if you need to know more information before heading to the South of Europe, check out our top Italy travel tips.
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Best villages and towns in Tuscany
Siena
Siena is Tuscany’s second largest settlement and, as a result, has plenty to see and do for even the most discerning of travellers. Best seen in the shoulder season (i.e. spring or autumn) in order to combat the sheer temperatures of the summer months but be able to enjoy the medieval city with good light and favourable weather conditions, the historic city centre of Siena is listed as a UNESCO world heritage site.
Once in the city, there are plenty of activities you’ll love, and as well as a fantastic Italian food scene, Siena offers plenty for culture and history lovers.
While the Piazza del Campo is the city’s main square, around which everything else in the town is situated, the Duomo di Siena (Siena’ Cathedral) is one of the most beautiful in the entirety of Italy. For more inspiration, be sure to check out the best things to do in Siena.
Lucca
Located alongside the Serchio river in the heart of Tuscany, Lucca is a must-see for architecture lovers, particularly those of the medieval kind.
After all, the Tuscan town boasts well-preserved Renaissance walls which encircle the town, as well as a plethora of churches. So numerous are the ecclesiastical buildings in Lucca, that the settlement is sometimes called ‘the city of a hundred churches’.
Much of the town is constructed around the Piazza dell’Antifeatro, which in turn is constructed on what would have been the central point for Roman life some two millennia or so ago. Other highlights and things to do in Lucca include the Delle Ore Tower and the Guinigi tower.
Florence
Of course, the most famous town in Tuscany is actually its capital city. Known as Firenze in Italian, Florence is a beautiful settlement characterised by its beautiful Renaissance architecture and fascinating medieval history.
Best-seen over the course of a long weekend, and even longer if you have the time to spare, highlights include the fantastic Duomo (officially known as the Basilica di Santa Maria del Flore), enjoying the art of the Uffizi Gallery, and admiring the Ponte Vecchio at sunset.
For more inspiration, be sure to check out our suggested one day in Florence itinerary and how to spend 3 days in Florence.
Cortona
A hilltop Tuscany town with a history dating back all the way to the time of the Eturscans, and perhaps even beyond, Cortona can be found in the province of Arezzo and is well worth visiting over the course of a day or two, provided that you have the time.
Once in Cortona, asides from wandering around the medieval town, one of the best things to do is to visit the Etruscan Academy Museum (Accademia Etrusca), which showcases collections of ceramic, bronze, and funerary artefacts from Cortona’s Etruscan past.
The museum also comprises of an archaeological park, which features the ruins of Roman roads and former city fortifications. In order to truly appreciate Cortona, you’ll want to book an overnight stay to be able to truly soak up the ambiance of the town.
Greve in Chianti
If there’s one area in particular in the Tuscan countryside you simply must frequent during your time in the boot-shaped country, it’s the wine-country area of Chianti. Known for its rich reds, the little villages that surround the swathes of vineyards are a must-see and that of Greve in Chianti is simply no exception.
Located around 30 kilometres to the South of Florence, Chianti offers little by way of tourist attractions, with the exception of its many wine-related activities.
Instead, the charm of Chianti lies in its laid back nature, not to mention the many beautiful castles which are just a short drive away and can be found set against the backdrop of the beautiful Tuscan countryside.
Volterra
Enthusiasts of medieval architecture will be delighted to discover Volterra, a hidden gem located a little off the beaten tourist track, but well worth a visit nonetheless. A tiny town located just a few hours away from the town of San Gimignano, the best of Volterra can be seen over the course of a long afternoon.
Once in Volterra, some of the best things to do include admiring the town walls, which include half a dozen gates allowing entry and exit from the city.
In the very heart of the Tuscan town, you’ll soon discover the Palazzo dei Priori, which features a belfry offering fantastic views over the town and beyond, as well as medieval frescoes dating back many centuries.
Other highlights of Volterra include visiting the Duomo (Cathedral) and baptistry, as well as delving even deeper into the past and looking at some Roman history.
After all, Volterra is home to the ruins of an impressive Roman theatre and the settlement is thought to have been continuously inhabited since at least the 8th-century BCE.
Pisa
If you’ve ever heard of famous Italian monuments, then no doubt you’ll have heard of the leaning tower of Pisa. Though it must be admitted that, of all the beautiful towns in Tuscany, Pisa is one of the most touristed, you simply must visit at least once… If only to say you’ve been!
Other highlights of the Italian town of Pisa include its cathedral (known as ‘Duomo’ in Italian), botanical garden, and more Medieval buildings than you could possibly count.
Easy to visit as a day trip from Florence, I recommend no more than an overnight stay in Pisa if you wish to make the most of your time in Italy. For more inspiration, check out the best things to do in Pisa.
San Gimignano
Though a little smaller and off the beaten path than some of the other Tuscany towns listed here, San Gimignano has the kind of charm which is hard to come by in today’s world, making it one of the most beautiful places to visit in the region.
Best-known for its fourteen well-preserved medieval turrets which rise high above the town’s landscape, and all dating back to the Middle Ages.
While the entirety of San Gimigano is encircled by 13th-century, other things to do include admiring the centrally located Piazza della Cisterna and frequenting the local market, which is open every Thursday.
For those wishing to glean a bird’s eye view from above, which offers a glimpse of the rooftops of this Tuscan town, as well as the possibility to gaze onto the rolling hills beyond San Gimignano’s city limits, a trip up the Torre Grossa is an absolute must.
The only tower which is open to the public, the structure dates all the way back to the 12th-century. Of all the towns in Tuscany, San Gimigano is most certainly one of the most beautiful!
Pienza
A charming hilltop town which remains a little off the beaten path despite the rise in popularity of Tuscany over the past few decades is that of Pienza.
Characterised by its location in the heart of the region of Val d’Orcia, Pienza is most famous for its pecorino sheep’s milk cheese which is sold in many of the shops across Pienza.
Other highlights of Pienza include discovering the central Piazza Pio II, around which the rest of the historic town is centred and admiring the architecture of the Duomo (cathedral) of Cattedrale dell’Assunta, which boasts some particularly fine works of art.
Montepulciano
Yet another charming medieval hilltop town that visitors will love discovering while in Tuscany is that of Montepulciano. This town is fairly substantial in size and boasts a population of around 14000 residents, as well as plenty of visitors during high season (i.e. in the summer months).
The town of Montepulciano is also the name of a red wine that is often used in chianti wines and so the Tuscany settlement is probably best associated with the rich red tipple.
Other highlights of Montepulciano include discovering the delightful historic square of Piazza Grande and the Renaissance ecclesiastical building of the Sanctuary of the Madonna di San Biagio.
Montalcino
Situated to the west of Pienza, the spot where Montalcino can now be found has been inhabited for thousands of years, and perhaps as far back as the Etruscans.
Like many towns in Tuscany, Montalcino is surrounded by olive groves and vineyards which are used to produce the famous red wines that now come from the region.
Rather interestingly, Montalcino actually takes its name from the fact that the area surrounding the town was once surrounded by a type of oak tree.
Today, highlights of this delightful settlement include discovering the glass and bottle museum which explores the history of glass and bottling in the area (Museo del Vetro).
Other highlights include snapping photos of the ancient cobbled lanes and façades, and visiting during the summer Jazz & Wine Festival which takes places in July every year.
Monteriggioni
This Tuscan settlement has around 9000 residents and is particularly worth a visit thanks to the fact that it’s surrounded by a well-preserved medieval wall. So beautiful is Monteriggioni that it’s often referred to as the ‘pearl of Tuscany’ and is even referenced in Dante Alighieri’s Divine Comedy.
The wall itself has encircled the village since the 13th-century when it was constructed by the Sienese during their war with the Florentines. Other than admiring medieval architecture, select highlights and things to do in Monteriggioni include sampling local cuisine and visiting local vineyards.
Arezzo
Yet another delightful Tuscan city which can be found in the East of the Italian region is that of Arezzo, which is home to a population of around 100,000 residents. The city is best-known for its shops and boutiques, with everything from art galleries to clothing stores dotted around the heart of town.
Those searching for beautiful antiques and vintage wares will also be delighted to discover that, on the first Sunday of the month (and the Saturday before it), there’s a fantastic antiques market that is widely considered to be the best in Tuscany.
On this day, up to 500 vendors from all over Italy head to Arezzo to tout their wares. Established in 1968, the Arezzo antique market is the oldest of its kind in Italy.
Other highlights of Arezzo include enjoying a coffee in the Piazza Grande, checking out the grand cathedral, and heading to the National Museum of Medieval and Modern Art.
Furthermore, if you’re looking for a base in Eastern Tuscany with plenty of food and accommodation options, then Arezzo is the place to stay.
Pitigliano
A little more off the beaten path when it comes to towns in Tuscany, Pitigliano can be found in the South of Tuscany. Situated to the south of Rome, most of the buildings in town are hewn from volcanic rock.
Once in Pitigliano, one of the best things to do nearby is to head to the nearby Vie Cave. These ancient pathways were carved by hand through rock faces during Etruscan times.
Some of these ancient roads are particularly impressive considering that some of the rock that was carved through is twenty metres high.
Pontedera
Unlike many other towns in Tuscany, Pontedera is more of an industrial town (many settlements in the region of Toscano actually make their money from tourism). Indeed, Pontedera is best associated with the Piaggio motor company and with wine production.
For those who want to discover more about the history of Piaggio vespas, there’s even a small museum in town that showcases exhibitions highlighting the history of the company. Elsewhere in Pontedera, there’s plenty of galleries featuring contemporary art.
Map of Tuscan towns
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Sophie Nadeau loves dogs, books, travel, pizza, and history. A Francophile at heart, she runs solosophie.com when she’s not chasing after the next sunset shot or consuming something sweet. She splits her time between Paris and London and travels as much as she can! Subscribe to Sophie’s YouTube Channel.