6 Best Places to Stay in Tuscany: Cortona, Lucca, Montepulciano & More

Florence is great, but sometimes you need to get outside of the big city! Luckily, you have the Tuscan countryside just waiting to be explored. Renowned for its breath-taking landscapes, the best places to stay in Tuscany often enjoy the benefit of being nestled amidst rolling hills, vineyards, and olive groves.

The views from these towns can be stunning and provide a sense of serenity and natural beauty. And, luckily, they are typically less crowded and less influenced by mass tourism, preserving their original charm and beauty. The architecture, narrow streets, and quaint squares often retain their traditional character, providing an opportunity to step back in time.

Have a look at our recommendations for the best towns and places to stay in Tuscany:

The colourful view from the hilltop town of Piazza San Pietro, Tuscany.

Lucca

Just a half-hour’s drive from Pisa you’ll find Lucca, a town dating back to Roman times. Unlike larger tourist hotspots in the region, Lucca has managed to maintain a more intimate and laid-back atmosphere. And its historical heritage is well-preserved, making it perfect place to stay and explore over the course of a few days.

Walking through the town’s narrow streets, you’ll encounter beautifully preserved medieval architecture, ancient churches, and Renaissance-era buildings. Don’t miss landmarks like the stunning Lucca Cathedral (Duomo di Lucca), the Guinigi Tower with its oak trees on the top, and the Piazza dell’Anfiteatro, a unique circular square built on the remains of an ancient Roman amphitheater.

Lucca is perhaps most famous for its well-preserved city walls, which encircle the entire historic center. The walls are wide and provide a lovely promenade with beautiful views of the town’s rooftops and surrounding countryside. It’s an excellent place for a stroll, bike ride, or our favorite activity – a picnic!

San Michele in Foro, one of Lucca’s many beautiful buildings.

Pisa

Yes, Pisa’s got the Leaning Tower, but that’s not the only reason to go.

Just a half-hour’s drive southwest of Lucca, Pisa reached the height of its dominance in the 11th to 13th centuries. Thanks to the stunning churches, palaces, streets and squares of the era, Pisa still feels like a medieval powerhouse today. Come on the last Sunday of June to see the Gioco del Ponte, a series of battles staged in medieval costume every year since at least the 16th century. And, okay, the Leaning Tower is pretty cool, too.

Another great reason to stay in Pisa? The city has a fantastic dining scene! Don’t miss the best restaurants in Pisa, brought to you by our food-loving friends at Devour Tours.

Insider’s tip: Visit the Leaning Tower in the evening, as the sun’s just setting and after the tour buses have gone.

An estimated 5 million visitors make their way to the Leaning Tower each year!

Montepulciano

Are you a wine-lover? Add this place to the list. If you´re not a wine-lover then we think that you will be after visiting this place.

Montepulciano is another one of our picks for the best places to stay in Tuscany. It’s biggest claim to fame is its Vino Nobile di Montepulciano, a DOCG-rated wine that’s been consumed since the Middle Ages and is considered one of Italy’s best. You could spend a whole afternoon here wandering the small town’s medieval streets and taking advantage of the free wine, meat, and cheese samples offered in the stores, but don’t miss the town’s smattering of lovely palaces and churches, either.

Then again, if you do spend your whole time in a wine shop, you’re in good company: After Henry James left Montepulciano, he said he struggled to recall the details of the town… because he’d spent all his time drinking!

Montepulciano and its wine are representative of Tuscany.

Montalcino

Another town on our list of the best places to stay in Tuscany is Montalcino. It is smaller than Montepulciano (at some 5,000, its population is about a third of Montepulciano’s), and so it is also less touristy, even though its claim to fame is similar: It produces Brunello di Montalcino, often considered to be Italy’s best wine.

Other than that, the town’s top boast is its Museo Civico e Diocesano d’Arte Sacra, with a wealth of medieval and Renaissance works surprising for the town’s size. There’s also a majestic 14th-century castle, still complete with a public park and walk along the ramparts.

Small towns are full of history and secrets to be discovered.

Arezzo

This town served as the backdrop for scenes from Life is Beautiful, and when you come here, you see why: The historic center of Arezzo is lovely and unspoiled. Its tranquillity belies a powerful past that included being one of the 12 Etruscan capitals and then, in the Middle Ages, a wealthy independent republic. Now home to nearly 100,000 people, it’s a hot spot for art and culture lovers.

Arezzo’s Church of San Francesco boasts a great cycle of frescoes by 15th-century master Piero della Francesca. Vasari’s frescoes in the Casa Vasari (Via XX Settembre, 55) depict an artist’s life journey, and the Archaeological Museum (Via Margaritone, 10) displays numerous ancient finds.

Perhaps it’s not surprising that Petrarch, the “father of humanism,” was born here in 1304.

Piazza Grande, the main square in Arezzo.

Cortona

After Frances Mayes wrote about living here in Under the Tuscan Sun, Cortona, home to a population of around 22,000, wound up indelibly on the tourist map.

We think this town, located smack in the middle of Italy, is well worth a stop for a day or an afternoon. The views alone are gorgeous, spreading from this dramatic hilltop town over the rolling countryside and Lake Trasimeno. And there are lots of worthwhile sites, like the Museo dell’Accademia Etrusca, chock-full of ancient Etruscan gems from the nearby area.

The views alone are worth exploring Tuscany far and wide.

FAQs – Best places to stay in Tuscany

How much time should I stay in each Tuscan town?

It depends on your pace and interests. Smaller towns like Montalcino or Cortona can be enjoyed in half a day, while Lucca, Pisa, or Arezzo are worth at least a full day or an overnight stay to explore their history, art, and food scene. Wine lovers may want to linger in Montepulciano or Montalcino for tastings and cellar tours.

When is the best season to visit Tuscany’s smaller towns?

Spring (April–June) and early autumn (September–October) are ideal. The weather is mild, vineyards and olive groves are lush, and local festivals are often in full swing. Summer is beautiful but can be very hot and crowded, while winter offers quieter streets and a more local atmosphere.

Are these towns expensive to visit or stay in?

Generally, they’re more affordable than Florence or Siena. Accommodation, meals, and wine tastings in places like Montepulciano or Montalcino can be good value, especially if you book locally-run agriturismi (farm stays). Pisa and Lucca, being more popular, may be slightly pricier, but you’ll still find plenty of budget-friendly trattorias and family-run hotels.

How do I get around between the towns?

The easiest way is by car, which gives you flexibility to explore the best places to stay at your own pace and stop at vineyards or viewpoints along the way. Trains and buses connect bigger towns like Pisa, Lucca, and Arezzo, but hilltop towns such as Montepulciano and Montalcino are best reached by car or organized tours.

What local specialties should I try in each town?

Every Tuscan town has its own flavor! Lucca is famous for farro soup and olive oil; Pisa for cecina (chickpea flatbread) and fresh seafood; Montepulciano for its Vino Nobile wine; Montalcino for Brunello di Montalcino; Arezzo for hearty stews and rustic breads; and Cortona for traditional Tuscan pastas and truffle dishes. This list of the best dishes in Umbrian and Tuscan cuisine will wet your appetite for sure.

Ready to see Tuscany’s rolling hills, medieval villages, and world-class wines for yourself? Join our Tuscany Day Trip from Florence, where you’ll explore charming hill towns, taste incredible wines, and soak up the very best of the Tuscan countryside—all in one unforgettable day.