Tuscany is brimming with beautiful towns and cities – whether it’s the iconic grandeur of Florence’s Duomo or the teetering towers of San Gimignano, there’s plenty to explore. These 15 striking destinations should be at the top of your list.
Tuscany is one of Italy’s most beautiful regions. With rolling hillsides sprawling inland from the beautiful Mediterranean coast and taking in incredible historic towns and cities, including Florence, Siena and Pisa, there is so much to see and do in this beautiful location.
Whether it’s tasting wine from the Chianti, Brunello or Nobile regions, or taking in historic sites dating from the Etruscan era through the Roman dynasty, Middle Ages and Renaissance to today, visitors to Tuscany are spoilt for choice when choosing what to see or do.
I’m speaking from experience, having recently come back from yet another visit to the region where I completely fell in love with the rich cultural, artistic and architectural splendour and the stunning landscapes.
So, without further ado, let’s dive in and help you find out where to go on your visit to Tuscany.
Must-Visit Cities and Towns in Tuscany
Florence
Anyone who’s read my guide to Florence knows just how much I love this city. Its incomparable architecture, stunning art galleries and food markets that attack the senses in incredible ways are only part of the reason Florence does it for me.
Explore the stunning gardens dotted around the city and visit the world-famous Duomo di Firenze.
Of course, no visit to Florence is complete without taking time to explore the awe-inspiring unmatched collection of Renaissance Art at The Uffizi or Galleria dell’Accademia that includes Michaelangelo’s most famous works, including his sculpture of David.
Lucca
Lucca is less renowned than some of its Tuscan siblings, which makes it a fabulous hidden gem. And others’ loss is your gain.
Surrounded by Renaissance-era walls, the city has gorgeous tree-lined streets where you can stroll, cycle, or jog (if you’re so-minded) while enjoying the stunning city views.
Attractions include the historic Duomo di San Martino the Palazzo Pfanner, which was used as a location for the Nicole Kidman film Portrait of a Lady and contains frescoes by Scorsini.
While there, visit the superb 18th-century restaurant Buca di Sant’Antonio to try their rabbit pate and tortelli Lucchese! I’m still dreaming about my meal in that restaurant.
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Siena
The highlight of any visit to Tuscany for history fans, Siena is one of the most beautiful Medieval cities in the world.
Historically a power that went head to head with Florence, Siena’s pedestrianised city centre instantly transports you back to the Middle Ages. Access to the city centre from the outskirts is via foot or cannily placed elevators.
Some of the city’s charms include the Piazza del Campo, where the historic Palio horse races occur twice a year, the Cathedral, and the awesome Santa Maria Della Scala gallery in the old Hospital.
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Pisa
Think Pisa and you’ll no doubt think about the famous Leaning Tower unless you’ve been visiting other planets until now. And while that is a must-visit, there is a bucket-load of other things to see and do in this beautiful city.
The Camposanto was founded in 1277 to house graves and is devoted to the dead, while the Sinople Museum is decorated with frescoes and cartoons.
Grab a ticket that allows you to visit the Cathedral and Baptistery before heading to a local restaurant to taste Pisano focaccia, called cecina, and the ribollita stew.
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Volterra
Famous for its alabaster stone, Volterra, one of Tuscany’s most ancient cities, was part of the Etruscan confederation at the beginning of the 4th Century BCE. Some hints of that age remain visible today, such as the Acropolis and Roman Amphitheater.
I’m not going to lie, I only got a chance to visit Volterra on my visit to Tuscany last month and it has catapulted itself to the top of my list of favourite towns in Tuscany. It doesn’t garner nearly the same number of crowds as some of the other towns but it really is beautiful.
Some of the many highlights include the Civic Hospital, which consists of a small Etruscan Museum, the Cathedral of Santa Maria Assunta and Baptistery and the Medici Fortress.
If you have a strong stomach and enjoy the weird, visit the Torture Museum before grabbing an alabaster souvenir at one of the many cute boutique stores.
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San Gimignano
I was something of an E.M. Forster obsessive for much of my teenage years, and I always wanted to visit San Gimignano, the town on which he is thought to have based the town of Monteriano in Where Angels Fear to Tread.
Nicknamed the medieval Manhattan of Tuscany, the towers that dot the skyline were built by the town’s affluent families that competed to produce the biggest and best one.
The views from the Torre Grosse are stunning, arguably the best in Tuscany, which is quite a claim! Other highlights include the Palazzo Comunale, Galleria Continua and Cathedral. When you’re hungry, the Locanda La Mandragola is the place to eat.
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Montalcino
Often overlooked by Tuscan tour guides, Montalcino was a real personal highlight from last month’s Tuscan jaunt.
Don’t miss it; do add it to your Tuscan itinerary. Home to the famous Brunello wine, that’s just one of the many highlights of this gorgeous town.
Visit the Locanda Demetra and Montalcino Cooking School to learn how to create some Tuscan masterpieces to wow your friends back home, and indulge your historical soul with trips to the Temple of Brunello Museum and Montalcino Fortress.
The hidden terrace at Il Moro is a beautiful spot for your evening meal.
San Quirico d’Orcia
If you want to strip back the tourist veneer of Tuscany, then San Quirico d’Orcia is one of the best places to do so.
The perfect location to explore a Tuscan town that isn’t inundated with tourists, I loved taking a relaxing stroll through the Leonini Gardens.
Of course, no Tuscan town is complete without a beautiful church, and the Church of Santa Maria Assunta delivers, as does the Collegiata of San Quirico D’Orcia.
Meanwhile, take yourself to the scenic point lined with Cypress Trees before exploring the endless array of restaurants lining the town’s streets.
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Cortona
Perched near the Umbrian border, Cortona is where some beautiful towns and villages blend. Sat atop a hill, Cortona was catapulted into the public consciousness by the film Under the Tuscan Sun.
With beautiful Etruscan heritage, one of the town’s biggest attractions is MAEC, which shows glimpses of this long history.
Much of the buildings are made of Cortona grey stone rather than Tuscany’s terracotta or golden hues. Take in the Cortona Cathedral, Fortress of Girifalco and Piazza Della Repubblica before eating the Bison Tartare at the Ristorante Il Preludio.
Montepulciano
Montepulciano is one of the busier towns in Tuscany that is exceptionally hilly even by Tuscan standards. So, make sure you have sturdy, comfy walking shoes!
This town dates back to the 4th century BCE and remains one of the most beautiful places to add to your Tuscan itinerary.
Big attractions include the Poliziano Winery (a short 5-minute drive outside of town), which opened in 1961 and now contains 170 hectares of organically maintained vineyards.
Otherwise, head to the Medici Fortress, which has beautiful botanical gardens, and the clocktower at the Palazzo Comunale, which offers breathtaking, Instagrammable views across the town and surrounding area.
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Monteriggioni
Monteriggioni is a tiny town around 10km from Siena that was built in the 13th century by the Sienes to protect the city from attacks from the Florentines.
The Medieval fortress at the top of the hill offers stunning views across sweeping Tuscan hills, while the city walls are well worth walking.
The Arme Museum has plenty of old armour and swords, which didn’t grab my fancy. Instead, I enjoyed browsing the artisanal stores along the two main streets.
For food, the Ristorante Le Torri Monteriggioni is a beautiful traditional Tuscan restaurant in the central Piazza well worth spending a leisurely couple of offers.
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Pitigliano
A small hilltop town south of Montepulciano, Pitigliano is carved from volcanic stone and within easy reach of the thermal waters of Bagno San Filippo.
Dating back to the Bronze Age, there is evidence of remains in local museums and an Etruscan community dating back to the 6th century AD.
The San Pietro e Paolo church dates back to at least 1061 and is a beautiful fusion of medieval and baroque styles. Le Vie Cave, or excavated roads, is a fascinating archaeological site.
There is a Jewish Museum, Synagogue and Ghetto that traces the town’s history with Judaism from 1556 through to World War II, where it was a haven for persecuted Jews.
Top Tip
Pienza
Pienza is a small village in Southern Tuscany in the stunning Val d’Orcia. Located amidst gently rolling hills and stunning natural landscapes, the town became the “ideal city of the Renaissance” thanks to the money of its most famous son, Pope Pius II.
The beautiful Pieve di Corsignano is a delightful Romanesque church with three naves that contains the original font where Pius II and his nephew Pope Pius III were baptized.
If you’re in town in early September, the Fiera del Cacio is unmissable, a festival devoted to pecorino cheese! Yes, please!
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Livorno
Although you don’t necessarily associate the beach with Tuscany, Livorno lies on Italy’s west coast and is well-known for its vast modern harbour and medieval fortifications.
Seafood plays a big part in Livorno’s culinary life, while the city is full of vibrant nightlife as well.
Head to the old fortress on the harbourside built to defend the city from invasion by regional rivals or attacks from foreign enemies. The maritime theme continues at the fabulous Natural History Museum, including skeletons of whales and botanical gardens.
The Old English Cemetery is worth a visit to see the final resting places of some famous travellers of yesteryear, including Scottish writer Tobias Smollet.
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Arezzo
Anyone familiar with the beautiful Oscar-winning film “Life Is Beautiful” will recognize Arezzo, which makes this Etruscan-era beauty a well-worthy addition to this list.
The wonderful Medieval Square is the perfect spot to sit quietly, sip a coffee or glass of wine and let the world go by.
Visit the Church of San Francesco and see some fabulous frescos by Piero della Francesca. At the same time, the Medieval Church of Santa Maria della Pieve and the city’s Cathedral are also great visits.
The first weekend of every month sees an excellent Antique Fair pop up in Piazza Grande, well worth a visit if you’re in town.
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Practical Tips for Exploring Tuscany
- You can explore many of the towns and cities in a day. Some of the smaller ones can be explored in a couple of hours. However, I recommend taking things leisurely rather than rushing to cram too much into a short time.
- You can use buses and trains to access most of the towns and cities in this article, but to fit in with the leisurely pace, I think the best way to explore Tuscany is by hiring a car and going at your own pace.
- Make sure you have sturdy and comfy footwear to explore the best towns and cities in Tuscany on foot. Some streets and town centres weren’t built with cars in mind, so it’s worth parking in the outskirts and walking in.
Towns and Cities in Tuscany: Map
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