Six Beautiful towns in Tuscany to avoid crowds

Is it too late to enjoy peace in Italy? Not if you know where to go.

Beautiful Italy has a tourism problem. There are too many visitors. Or at least, too many visitors in the same places at the same time. Venice is the poster child for overtourism in Italy but the rest of the country faces similar challenges. In Tuscany, the city of Florence and to a lesser extent Pisa and Siena attract more tourists than the narrow medieval streets and number of hotel rooms can handle.

So why not check out some beautiful towns in Tuscany that offer the same great food and wine and fascinating history but with more elbow room?

I’m not suggesting you’ll be the only tourist in town, especially if you’re travelling in high season summer. All of Tuscany is on the tourist trail, with good reason. But in these places you won’t struggle to find a place to sit and eat your gelato, or have to stand in line for hours to enter a church. And you can contribute to responsible tourism instead of overcrowding. Did I mention they are also beautiful?

These places between Rome and Florence make excellent lunch spots or day trips. But also fine places to overnight or spend the weekend when you want to slow down.

Here are my favourite beautiful towns in Tuscany that are worth a day trip, and more.

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Montepulciano

This may be the hilltop medieval town of your dreams. If you dream of stunning views of the Val d’Orcia, wine tastings, winding cobblestone streets…and vampires.

Montepulciano (pop: 14,000) was a filming location for Twilight: New Moon, which is not why we came, but it did give our visit extra Goth Points. This compact car-free town also has romantic Renaissance vibes.

Like most beautiful towns in Tuscany, there’s a lot of history here, dating back to the 14^th and 15^th centuries, when Montepulciano was a hometown to many rich noble families including the Medici. The main square is Piazza Grande. Look up at the clocktower and you might catch a clown-like figure called Pulcinella striking the bell on the hour. You can pay to climb up for sweeping views or pay a visit to the Fortress (now a cultural centre) which also has gorgeous views from their back terrace. Go inside the Gothic St. Augustine’s church to see altars and frescos by artists such as Orvieto, Pomaracio and a wooden crucifix from the 1400s attributed to Donatello. Ask around if you want to see the relics of Pucci-Franceschini.

Montepulciano loves festivals, so you might catch a wine festival, an olive festival, a chocolate festival, or the traditional Bravio dell Botti, a barrel race where locals roll (aka push) a 80kg barrel along an uphill route, going strong since the 14^th century. If you’re looking to avoid crowds in Tuscany, pick another date for your visit here.

This place is steep. Depending on your mobility, you may want to park at the Porta al Prato and walk up to the main square, or you can drive up and park just outside the town limits. Either way, see most of Montepulciano involves walking up and down and up again. It’s worth it if you can. For a small place, they had a surprising amount of cool shops, including clothing and quality crafts. And, of course if you like wine, there’s wine tasting every few steps, including some cool underground wine bars.

Don’t miss the beautiful Church of San Biagio, located outside the main town at the bottom of the hill. (You can park nearby.) Some say Michelangelo was inspired by the style when creating St. Peter’s Basilica.

Montepulciano is located 124 km southeast of Florence, and 186 kilometres north of Rome. There’s enough here for a full day and night and if you want to enjoy all the wines there are many cute villas located just outside the city walls to make it a weekend.

Something unusual to do in Montepulciano: The Torture Museum

Pienza

Say cheese! This tiny town (pop: 3,000) is known for its sheep cheese called pecorino, which is a perfectly fine reason to visit if you ask me.

Pienza’s name means Pius—as in Pope Pius II, who was born here and decided to revamp the otherwise village of no note into “the ideal Renaissance town.” according to “humanist urban planning” concepts. Building started in 1459 and today the UNESCO World Heritage Site looks pretty much the same as it did then.

The main Pienza piazza has a gorgeous Gothic Cathedral with masterful religious paintings and floor tombs (similar to the Basilica Santa Croce in Florence). The Archeological Museum displays Etruscan and Roman artifacts and explains the history of the town.

But back to the cheese….. We lined up to enter the tiny La Bottega del Cacio and then had to quickly choose from dozens of different kinds of pecorino. I had never tried any before, and it didn’t seem like the kind of place you can linger tasting while others wait outside, so I just went for things that looked and sounded interesting. One of them was covered in some kind of grass. I choose Pecorino with Pear, not sure why! I probably should have just picked the most famous—the one with black pepper—because this was not my favourite thing I ate in Italy. I don’t regret it though, these were cheeses I cannot get at home!

Pienza is located 180 km north of Rome, and 50km south of Siena. I found it easier to navigate than some of the other small towns in Tuscany on this list. You can park fairly close to the centre, and it’s flat. But the ratio of visitors to locals was noticeably higher. And apart from pecorino we mostly saw souvenir shops. Still, if you like specialty cheese or study urban planning I would try to grab lunch here.

Chuisi

How much do you know about the Etruscans? Whether you’re like me and never heard of them before, or you’re already fascinated by this civilization who ruled Italy before the rise of Rome, the town of Chuisi (pop:8,500 ) is a beautiful town in Tuscany that you need to visit.  

This historic place was one of the first and most important Etruscan cities, and the Civic Museum will tell you all about it. This is more like an underground city of tunnels with the largest collection of Etruscan funeral urns and tombs in Italy, around 3,000. It’s also one of the coolest places to retreat to if you’re suffering from a summer heatwave.

A few km outside of Chuici, the Catacomb of Santa Mustiola is one of only three catacombs in Tuscany, and the only one open to tourists—by guided tour. I absolutely loved exploring the ruins of this Christian burial place dating back to the 3^rd century. Our tour guide did his best in English for us although everyone else spoke Italian but I didn’t mind just wandering and letting my imagination tell me the story of the symbols carved into tombs and walls. This is not a catacombs filled with bones (although we did see one skeleton poking out of a crack) it’s more about the structure itself. It was absolutely a highlight of my trip to Italy and felt quite off-the-beaten tourist trail but so, so fascinating!

Visits are by guided tour only and limited to one group per day. Enquire in the town of Chuisi at the Cathedral Museum. (As far as we can tell, you can’t buy these on-line, so you have to visit the town, get your tickets, and then drive back out to the site. If your Italian is good, you can also try emailing them.)

Chuisi is located 160km north of Rome. About 10 minutes-drive from the town centre is picturesque Lago di Chuisi.

Chianciano Terme

Chianciano Terme is a true hidden gem. It’s situated on thermal waters and is home to several spas, including Theia, where I had one of the best nights ever at a night spa with live music and delicious dinner.

Time has not been the kindest to Chianchiano as a tourist hot spot—you might not feel it’s one of the most beautiful towns in Tuscany from the look of main street—but in exchange for that you get an authentic small-town Tuscan experience. We were staying in a farm nearby and made rituals of long morning walks into town for fresh baked goods or of driving to the gelato spot after dinner to watch locals socialize or take their walks. Oh, and of course it also has gorgeous views.

A short drive away is La Foce, a magnificent estate with landscaped gardens that are a must-see for all flowers lovers.

Chicanciano Terme was an affordable homebase to visit the rest of Tuscany on day trips. If you want to truly get away from crowds in Tuscany you should consider it. It’s located 160km north of Rome, about halfway to Florence if you’re headed that way.

Bagno Vignoni

Fancy a spa day? This charming village (pop: 30. Yes, 30!)  is built around natural hot springs. You can’t miss the hot pool—where most beautiful towns in Tuscany have a piazza, this one has an ancient pool. It’s for looking only. Sometimes there is artwork on display in the pool—we saw this lovely reflecting floating iceberg.

A short walk away you can dip your feet into some very hot thermal springs. If you want to get into the natural waters, follow the locals to a free bathing spot along the riverbanks called Parco dei Mulini. I’d describe this as a rustic, no frills experience and there are no facilities here, so pack what you need.

On the other hand, if you want to splurge there are full-service spas and hotels all around Bagno Vignoni. This spot does attract crowds so staying on site may be the best option so you can get out and enjoy in the morning before day trippers arrive.

Bagno Vignoni is located less than an hour’s drive south of Siena.

Prato

I never tire of the Renaissance glory of Italy. But! If you want to explore more modern art you can do it in Prato. It’s a city, not a town (pop: 195,213) but it seems to escape the overtourism despite being so close to Florence. So I put it on my list of beautiful places in Tuscany to visit if you want to avoid crowds.

Two great museums here punch well above their weight. The futuristic looking Luigi Pecci Centre for Contemporary Art houses the best of the avant-garde. And the Textile Museum, which celebrates the textile history of this region, Italian fashion and everything in between, is located in a converted 19^th century factory.

Don’t worry Prato has its traditions too: visit its Santo Stefano Cathedral on Christmas, Easter, May 1, August 15 or  September 8 when they bust out their prized artifact: the Holy Girdle of the Madonna—believed to have been worn by the Virgin Mary herself.

Getting Around the small towns in Tuscany

If you want to visit the most beautiful towns in Tuscany and you don’t have a car, I recommend asking your hotel or other accommodation for directions by public transportation. Some of these places can be reached by rail. There is also an extensive and affordable bus network. But with multiple companies, getting a local to explain the best way to go is a good idea.

I hope this list of beautiful towns in Tuscany has inspired you to travel outside of the most popular places and see more of what this part of Italy can offer. If you have a favourite I missed please let me know in the comments below!