Tuscany is arguably the most popular region in Italy, and there’s everything you need for the perfect holiday, from medieval towns to some of the world’s best wines, and, you guessed it – the best towns to visit in Tuscany.
You see, Tuscany allows you to take it slow and enjoy the pleasures of life, and the best part is that it just feels so good. That’s the exact reason why so many people keep coming every single year.
In this guide, we’ll discuss the 15 prettiest towns in Tuscany – but that’s not even the most exciting part. That’s right, we’ll also discuss how long to stay and how to get there, among other points.
Make sure to read until the end before traveling around these villages in Tuscany!
15 Best Towns to Visit in Tuscany
One thing everyone knows about Tuscany is the rolling hills, Florence, and all the scenes from “The Tuscan Sun.” That being said, there are so many more things to know about this part of Italy, and these hill towns in Tuscany are just the beginning!
I was lucky enough to live in Tuscany for a few years near Florence, and it’s honestly one of the best places in the world for a holiday. Let’s get started, I can’t wait to tell you more about these small towns in Tuscany.
San Gimignano
San Gimignano is a small town not too far from Florence, Tuscany, Italy. However, it is known mostly due to the white wines called Vernaccia and due to the large number of medieval towers (and towers are the first thing that you can see as soon as you arrive at the town).
The picturesque streets of San Gimignano are lined with old-fashioned, colorful houses. And of course, they are located uphill on which San Gimignano enjoys incredible spreads over beautiful regions of the surroundings. For example admire the beauty of the countryside by wandering from San Gimignano to Monteriggioni.
In addition to this, you can see a few monuments including the cathedral, one of the best examples of Gothic medieval architecture. The Palazzo del Popolo, a building located on the town’s main square, Piazza Cisterna. Plus, count few other notable sights on your San Gimignano bucket list and enjoy a Mediterranean lunch inside your rental house.
Of course, you can spend some time shopping or enjoying a cafe or restaurant with a view of the town.
Around every corner there is something always different to see, it was almost weird at times like your in some beautiful dream. I think it is a must see city if visiting Tuscany as it is like something out of a story, some buildings even have wonderful murals depicting people etc. It’s definitely worth visiting a few buildings of interest.
I traveled to San Gimignano a few years ago while living in Tuscany, and this was one of the best trips from Florence I have taken. I couldn’t recommend it enough. Also, if you’re in Italy for a special occasion (read, proposal!) then San Gimignano is a fantastic option.
Activities in San Gimignano
- Piazza del Duomo
- Palazzo del Popolo
- Tower and Casa Campatelli
- Piazza della Cisterna and its Towers
- San Gimignano Museum of Torture
Pienza
Pienza is an idyllic Tuscan town located about 80 miles southeast of Florence. It is popular for its architecture, which was built during the Renaissance under the auspices of Pope Pius II.
And I’m not going to lie – Absolutely won me over with this one. The city has often been called the ideal city of the Renaissance and became a UNESCO World Heritage site in 1996. It was relatively undiscovered, but now it is a big attraction for movie productions.
Pienza is now a major tourist attraction since much of it was renewed. It can boast of various landmarks like the cathedral of Santa Maria Assunta and also for the visitors.
Also, as Pienza is perfectly located in the Val d’Orcia you have some of the prettiest towns in Tuscany like Montepulciano or Cortona quite near to create a base for your travels. Once you’ve seen the tiny 700-person village, a visit to Pienza today means getting here before the tour buses (generally by 10 am) and staying at least until lunchtime.
I also traveled to Pienza on my road trip around Tuscany (the best way to get there is renting a car and driving) and I spent about 3 hours here. These were some of the best 3 hours I had in the region!
Activities in Pienza
- Piazza Pio II
- Pienza Cathedral
- Bishop’s Palace
- Palazzo Piccolomini and its Gardens
- See the views from the Panoramic Terrace
Siena
To visit Tuscany and not see Siena is just not an option. It’s only a one-hour drive from Florence, which is a nice incentive.
Siena is known for its beautiful medieval red brick buildings, an imposing gothic cathedral and Piazza del Campo, the heart of the town as well as Palazzo Pubblico, the town hall.
The historic town center of Siena is another UNESCO World Heritage site, and you can see why it’s always on the list of the best Tuscan towns.
Siena Cathedral (Duomo) is stunning, given that it’s made in the Gothic style, striped in black and white, while the Duomo of Siena contains art by Pisano, Michelangelo, and Bernini. People typically come to Siena to look at the Duomo (cathedral) and the museums that are part of that or to explore the historic palaces that you’ll see all over the center.
Adding to this, every summer brings the sound of hooves thundering through the streets of Siena as participants come to race in the Palio of Siena.
Crammed with plentiful art galleries, museums, squares, palazzos and churches, Siena can compete admirably with Florence as one of the finest smaller towns.
Somewhere with the loveliest cityscape left in Italy, Siena is one of the most charming in Tuscany you really have to visit at least once in a lifetime.
Activities in Siena
- Fonte Gaia
- Duomo di Siena
- See the Palio of Siena
- Battistero di San Giovanni
- Piazza del Campo and Palazzo Pubblico
Lucca
To experience a real touch of medieval Italy, Lucca is one of the most important Tuscan towns in Tuscany. This beautiful, authentic town enjoys a preserved wall constructed in the 16th century.
The wall spans over 4 kilometers and is perfect for a relaxed walk or a bicycle ride. Once hunger strikes, be sure to eat some of the local fare, like ribollita (a vegetable and bread soup) as well as Panzanella, which is a mix of bread and tomatoes.
Lucca is spread along the Serchio River and is one of the very few Tuscans that aren’t perched high up on a hill – That is convenient because you get easily get there by train from pretty much anywhere in the country.
There are many streets, tortuously winding on to radio in the middle to form the square of Piazza dell’Anfiteatro – like the amphitheater itself; but now a graceful circle with some buildings projected beyond the portico into the area.
It’s possibly the perfect place for a bit of people-watching while sipping a nice cold glass of Limoncelli. Twice a year it comes alive with a kaleidoscope of concerts, exhibitions, sporting competitions and fairs, with regular performances from Gusto Mascotte.
There’s simply too much to say about it and I highly recommend spending at least one day in Lucca to visit without feeling rushed – Thank me later!
I stayed in Lucca for 3 weeks on my trip around the region (yes, that’s long, too long I would say) and I genuinely loved it – One of the best Tuscan cities to visit!
Activities in Lucca
- Guinigi Tower
- Lucca Cathedral
- Piazza dell’Anfiteatro
- Ponte della Maddalena
- Walk Around the Town Walls
- Church of San Michele in Foro
- National Museum of Villa Guinigi
Volterra
Volterra was a robust Etruscan city at one time, but it’s predominantly known for its Italian artistry and the vestiges of its medieval antiquity. The Duomo, a wide 13th-century church, is the most eye-catching bit, surrounded by palaces and fortresses that include the Palazzo dei Priori, the Palazzo Pretorio, and a 13th-century palazzo.
However, the city has a number of attractions that could be worth your viewing, including a geothermic pool and a 13th-century town gate decorated with carvings in relief that symbolize Volterra’s commerce.
As with any Tuscan city, there are churches lining the streets, most notably the Cattedrale di Santa Maria Assunta. You must visit this ancient building, rebuilt from a former round Roman temple, standing next to the ancient high road that led to the Porta Collina.
There is so much to see in Volterra – here are some of my recommendations! Besides the Etruscan Museum and the Archaeological Museum, you can’t forget can also explore the Etruscan Acropolis and its Roman Theater.
You’ll see ancient monuments, carved initials in the walls, museums of glass, ceramics, weapons, pictures, and the lovely 14th- century fortress.
For the above reasons, I like to see Volterra and its surroundings as well as the Etruscan museum. I also wouldn’t leave without visiting the famous Palazzo dei Priori!
Activities in Volterra
- Roman Theater
- Etruscan Museum
- Palazzo dei Priori
- Volterra Cathedral
- Baptistery and Diocesan Museum
Monteriggioni
Next up is Monteriggioni – it’s a cute little town twenty kilometers north of Siena, just a 25-minute drive away. You’ll see street after street of charming stone houses, adorable shops, and welcoming cafes where you can sip an espresso or a glass of Chianti is inviting you to become a part of its relaxing atmosphere.
Monteriggioni is a good base for excursions to other museums or religious heritage sites in Mizoram.
Built by the Sienese in the 13th century, Monteriggioni’s walls and 14 towers look like they come straight from a fairy tale. You’ll find charming stone houses, cute shops, and cozy cafes where you can grab an espresso or a glass of Chianti and soak up the ambiance.
A second preference for spending time is possibly to visit several other museums and religious sites in the vicinity of Mizoram. Furthermore, it is also home to some of the most celebrated Montepulciano vineyards.
The main square, Piazza Roma, is the perfect spot to sit back and people-watch, all while imagining you’re in an episode of “Game of Thrones.” Alternatively, climb up to the Monteriggioni Castle for panoramic views over the rolling hills. That’s what you’re in Tuscany for, right?
Some places in Monteriggioni have a lot to give. This medieval gem is so compact you can explore the whole town without getting lost. Monteriggioni might be small, but it’s packed with character and charm.
Another option is Monteriggioni Castle – bound to give you a panoramic view of the Tuscan sunrise over the rolling hills. Let’s face it: that’s why you came to Tuscany!
Activities in Monteriggioni
- Piazza Roma
- Museum of Arms
- Church of Santa Maria Assunta
- Have Lunch at Osteria Antico Travaglio
- Walk on the City wall and its 14 Towers
Montepulciano
Montepulciano is another hilltop town in the southeastern part of Tuscany which is about an hour’s drive from Siena. This town is famous for its vineyards, wineries, and Renaissance architecture.
The town’s heart is the Piazza Grande, where you take a glass of the local wine and admire the unfinished brick Duomo. If the high you get from letting the wine go down your throat isn’t enough, there are many more cellars and tastings available near the square.
The beautiful hilltop town of Montepulciano is another regular stop on the southern part of Tuscany’s tourist trail, and for good reason. Montepulciano is famous for its vineyards, wineries, and full-blown Renaissance buildings, where you’ll find a flat walking around the town.
There are many wineries in Montepulciano that offer tours of the winery and wine tastings – making it the perfect place for any wine enthusiast to visit. Plus, Montepulciano actually has a fine number of traditional restaurants that serve well-known Tuscan dishes such as bistecca fiorentina and crostini di fegato.
Isn’t this all enough for you to come and spend some time in Montepulciano?!
Activities in Montepulciano
- Piazza Grande
- Palazzo Avignonesi
- Church of San Biagio
- Have a drink at Caffè Poliziano
- Church of Santa Maria dei Servi
Cortona
This town very much embodies the best of Tuscany: hilltop destinations brimming with culture, history and architecture, sprawling vineyards and olive groves, and of course, deep, pungent wines.
Cortona, a quaint and entirely walled Etruscan town located in the southern Tuscan province of Arezzo, rises to just about 600 meters above sea level on top of the slopes overlooking the valley below and Lake Trasimeno.
Even though the town is tiny (and all places are walkable), it has plenty of charming places to visit, including Diocesan Museum, Museo dell’Accademia Etrusca (often referred to as MAEC), and Sanctuary of Santa Margherita across the town, many of them in beautiful, ancient churches.
If you’ve heard of the book and movie Under the Tuscan Sun, you’ll remember this town.
Naturally, as part of the Chianti Classico wine zone, these hills practically drip with red wine. After a long day of sightseeing, there is no lack of spots to unwind with a glass in hand.
Get out and see the town, and have a glass of Chianti in your own piazza at sunset (by now, you could be feeling a little like a cast member of the famous Chianti). At the very least, you’ll want a few minutes here.
Activities in Cortona
- Convento delle Celle
- Etruscan Archaeology Museum
- Santa Margherita
- Piazza della Repubblica
- Diocesan Museum
Suvereto
Suvereto is a small quaint village situated within Livorno province of Tuscany, Italy. It is located on a hill amidst scenic natural beauty, which explains its forest, vineyard, and olive spreads that overhang the Mediterranean.
Suvereto’s tower rises above them all. This ancient jewel not only testifies to the medieval origin of the village but, in its cellars and numerous courtyards, often becomes the stage on which all kinds of events take place, such as concerts, exhibitions, and markets.
You won’t regret wandering aimlessly in Suvereto — all along the way, you’ll see stone buildings that’ll make you fall in love with this place, churches that tell you the life of the town and vineyards stretching into the horizon.
At the same time, please also do not miss the food. Highly reputed for traditional Tuscan authenticity, the foodie scene even extends to artisanal gelato. Eateries and ristorante in Cortona serve the best traditional Tuscan dishes.
If you love food, it is reason enough to do a food trip here and also why not to anyone who just likes to enjoy excellent meals.
Suvereto is an underestimated gem in Tuscany, and there is no direct flight or transportation that will take you there; you have to rent a car for yourself, so keep that in mind.
Activities in Suvereto
- Convent of San Francesco
- Church of San Giusto Vescovo
- Rocca Aldobrandesca of Suvereto and Its Museum
Pitigliano
Set on the tufa rock (it always reminds me of Ronda in Spain), Pitigliano looks like it’s coming straight out of a fantasy novel. And it’s one of Central Italy’s hidden gems.
Pitigliano gets the nickname “Little Jerusalem” because of its extensive Jewish history. You can still appreciate the historical value of these old houses as well as the rustic cultural experience.
Besides that, each has its charm. If you want to learn more about this aspect, I recommend visiting the Historical Archive of the Jewish Ghetto Museum in which you will discover that the bond between the Jewish tradition and Pitigliano’s Christian culture still is alive in what is considered one of the most peaceful places on Earth.
At the entrance of town is the ancient theater containing an interesting historical complex. You can exit the historically engrossed zone and climb up the path to arrive at the impressive Palazzo Orsini.
The synagogue, the emblem of the Jewish quarter, is where an entirely different kind of pilgrimage takes place—the journey of cultural intermingling preserved under one roof.
Pitigliano also boasts of some incredible caves that are chiselled right into the rock. While there are countless Etruscan caves to be found here, there are many that date back to the same period of time, but it has been transformed into underground cellars and wine production sites today. The most famous white wine from the region is Bianco di Pitigliano, an appellation that varies according to the grapes used and the blend of the harvest.
If you’re struggling to decide where to go, Pitigliano is definitely a great option, and it’s one of the best towns to visit in Tuscany!
Activities in Pitigliano
- Orsini Palace
- Cathedral of Pitigliano
- Piazza della Repubblica
- Fontana delle Sette Cannelle Fountain
Arezzo
Another one of the top towns to see when you’re exploring Tuscany is Arezzo. This central Italian town has many well-preserved Renaissance monuments as well as a lively arts and culture scene.
Arezzo is situated in an idyllic landscape, plainly exhibiting the lovely valleys, vineyards, and meandering broad streets surrounded by thickly forested hills. Needless to say, this is the perfect backdrop for taking photos, and your friends will love the shots on social media!
Unlike anywhere else in Tuscany, Arezzo features a charm of its own derived mainly from a sea of small red-brick houses that cascade all the way from steep hills to the city center.
These intensely beautiful shades are visible practically everywhere. While you’re here, I urge you to check out Arezzo’s picturesque old town and try some of the local cuisine.
Nestled in a tranquil setting but with innumerable attractions around, Arezzo is indeed one of the most popular spots in Italy, let alone Tuscany.
Activities in Arezzo
- Piazza Grande
- Duomo San Donato
- Parco Sandro Pertini
- Archaeological Museum of Arezzo
- Church of Santa Maria della Pieve
Anghiari
This is one of the best Tuscan towns for all the foodies and art lovers! If you’re looking to explore the coolest and best city in Tuscany while you’re based in Arezzo, Anghiari is the obvious answer.
Sitting on top of a hill, Anghiary displays some of the most splendid views of the valleys nearby, This town is pretty much the Elysium of architectural landmarks and medieval buildings.
Start your journey at the Palazzo Taglieschi, a museum with plenty of medieval artifacts, quirky sculptures, and even some ancient musical instruments. It’s like a treasure hunt through Tuscany’s past.
Then, stroll down to the Anghiari’s main square, Piazza Baldaccio. Grab a gelato and people-watch as the locals go about their day. It’s the perfect spot to relax and soak up the town’s laid-back vibe.
By the time you’re done with the main square and the museum, you’ll probably feel peckish, and Anghiari’s food scene is as rich as its history. Make sure to try some local dishes like pappardelle with wild boar sauce or a slice of rustic Tuscan bread with fresh olive oil.
Before leaving, take a walk along the ancient city walls for the best views. You’ll get a panoramic look at the lush Tiber Valley below. It’s the kind of scenery that makes you want to whip out your camera and never put it away.
Activities in Anghiari
- Museum of the Battles
- Church of Santo Stefano
- Museum of Palazzo Taglieschi
- Chuch of Santa Maria delle Grazie
- Have a Meal at Cantina Del Granduca
Castelnuovo di Garfagnana
What to do when in the heart of Tuscany? Well, visiting Castelnuovo di Garfagnana is an excellent option, and it’s one of the best towns to visit in Tuscany for different reasons.
Once you get there, start your visit at Piazza Umberto I, the town’s main square. Here, you’ll find the Rocca Ariostesca, a medieval castle that has stood guard over the town for centuries. It’s a great spot for a stroll and some photos.
As you wander through the steep, cobbled streets, you’ll come across charming shops and cafes. Stop by a local bakery for fresh focaccia or grab a cappuccino and watch the world go by. The locals are friendly and always ready to share tips on what to do next.
That’s right, when it comes to food, Castelnuovo di Garfagnana has you covered. Try the local farro soup, a hearty dish made from an ancient grain. As always in this part of Italy, don’t forget to pair your meal with some local wine!
If you’re in town during the festival season, you’re in for a treat. There are multiple lively summer music festivals, and there’s even a cozy autumn chestnut festival that brings the community together.
It might not be prevalent on the tourist map yet, but Castelnuovo di Garfagnana is one of these places that are hard to forget, so make sure to add it to your itinerary.
Activities in Castelnuovo di Garfagnana
- Rocca Ariostesca
- Teatro Alfieri Theater
- Fortress of Mont’Alfonso
- Hike Up to One of the Trails
Montalcino
Montalcino is the heart of Tuscany’s wine country! Famous for its legendary Brunello di Montalcino, this hilltop Tuscan town is a must-visit.
Start your adventure at the medieval fortress, Fortezza di Montalcino. The fortress offers stunning views of vineyards and the rolling countryside, making it the perfect spot to kick off your visit.
Wander through the charming, narrow streets, and make sure to stop by local wine shops for tastings. Don’t miss Enoteca La Fortezza inside the fortress for a top-notch wine experience. It’s a wine lover’s dream come true.
For a dose of history, head to the beautiful Sant’Antimo Abbey just outside town. This serene, picturesque Romanesque church adds a touch of tranquility to your trip.
When hunger strikes, indulge in Montalcino’s hearty Tuscan cuisine at a local trattoria. Try the wild boar ragu or pici pasta, and of course, pair your meal with the town’s famous wines.
Montalcino is a delightful mix of wine, history, and scenic beauty. Whether you’re a wine enthusiast or just someone who enjoys a good view and great food, Montalcino offers a little slice of Tuscan heaven.
Activities in Montalcino
- Palazzo dei Priori
- Fortress of Montalcino
- Cathedral of the Holy Savior
- Church of Our Lady of Soccour
- Belvedere di Montalcino Viewpoint
- Have Lunch at Taverna del Grappolo Blu
Pontedera
If you’re looking for the best Tuscan towns to visit, Pontedera should be at the top of your list. Situated only 30km from Pisa, this charming town is located in the heart of Tuscany, and it’s the perfect destination for a day trip in Tuscany.
Explore the town’s medieval streets and visit its famous churches and museums when you’re here. If you’re a fan of Tuscan wine, you’ll also want to tour one of the many wineries in the area.
And, of course, no trip to Pontedera would be complete without enjoying a delicious meal at ArteGrill, one of the best places to eat around.
Of course, visiting the leaning tower of Pisa is a must, but I highly recommend you come visit Pontedera once you’re done with your visit.
Activities in Pontedera
- Piaggio Museum
- Misericordia Church
- Misericordia Church
- Parrocchia del Sacro Cuore
- Walk Around the City and Via I° Maggio
Famous Towns in Tuscany – FAQ
Now that you know a little bit more about these villages in Tuscany, let’s answer some questions that first-timers have and that you may have too.
How Many Days do You Need in Tuscany?
A week in Tuscany is the perfect amount of time to fully appreciate its beauty. Spend 6-7 days, and you can see the key areas for touring, like Florence and Siena.
You could also fit in some leisurely drives through the Tuscan countryside, a Chianti wine-tasting session, and possibly even a cooking class. This pace enables you to hit up both recognized landmarks and hidden gems.
How to Get Around in Tuscany?
The easiest way to get around Tuscany is by car. You can rent a car in Italy and drive around Tuscany, which makes your day trips around much more convenient. We suggest hiring a car as the most comfortable and flexible choice.
Alternatively, you can take public transport around the region – trains and buses serve major towns but are less frequent. Look up the bus and train schedules now so you can plan your route and avoid confusion.
Lastly, and this is the most convenient option, you can join a guided tour from Florence to different parts of Tuscany, which is quite affordable and includes the most beautiful towns in Tuscany.
What is the Best Town in Tuscany?
In Tuscany, San Gimignano is the most famous and from the towns, the best town of all. It’s on the hill, and that’s a great place to see the landscapes.
The walled medieval town is stunning and filled with art and architecture from the 13th and 14th centuries. There are towering testaments to the height of hubris in the medieval age—province houses turned into vertical status symbols.
Despite being the most picturesque town in Italy, it’s worth noting that Florence is magical too, with incredible architecture, countless museums, and delicious food to die for!
Which is Better – Siena or Lucca?
Both Siena and Lucca are lovely and historic towns in Tuscany, but their experiences are altogether different. Siena is a hilltop medieval city well-known for its striking cathedral and other medieval edifices as well as an annual horse race, the Palio di Siena.
The historic center of Siena is traffic-free and full of enchanting, maze-like lanes and magnificent piazzas. It is also home to some amazing art museums and galleries and superb food and wine.
With its well-preserved Renaissance-era walls and narrow, cobblestone streets, Lucca is another charming walled city. The city is also known for the Lucca Summer Festival, which has featured performances by some of the biggest names in music, including Elton John and Neil Young.
The city is very bike-friendly, with a network of tree-lined bike paths, some atop the city walls.
In the end, the choice between Siena and Lucca completely depends on what you’re interested in. If you would like to explore the historical, architectural and artistic heritage of Tuscany, then Siena is most definitely your type of place.
If you love the architecture of the Renaissance era, love music as much as I do, and you are more into biking rather than walking, then Lucca is a better place for you to live out your true self.
More Italy Travel Guides
- Pisa Tour from Florence – Travel Guide
- 10 Best Day Trips from Florence, Italy
- Plan the Perfect 3-day Itinerary in Florence
- This is the Best Time to Visit Matera
- How Much Does a Trip to Italy Cost?
- Unique Places to Travel in Europe – Italy
Conclusion – Best Small Towns in Tuscany
There you have it – 15 of the most beautiful towns to visit in Tuscany. Whether you’re looking for culture and history, delicious food and wine, or stunning views, there’s something for everyone in this part of Italy.
From the UNESCO World Heritage Site of Siena to San Gimignano and Cortona, these were the most beautiful towns in Tuscany, Italy.
So make sure to add these destinations to your trip to Italy, you definitely won’t regret it.
