Best Towns and Villages in Tuscany

Tuscany is quintessential Italy.

Rolling green hills dotted with cypress trees, silvery olive groves and terraced vineyards. Ancient Etruscan settlements and medieval hamlets perched high in the hills. Renaissance cities packed with art. And some of the best food in the country.

I first visited as a wide-eyed Interrailer more than 30 years ago and I’ve returned many times since. I’m not done yet.

Here are the best towns and villages in Tuscany, from Pienza to Pitigliano, San Gimignano to Siena.

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Before You Start

To get a sense of where these places sit, use the map below, or click through for the interactive version.

In terms of convenience, flexibility and accessibility, exploring Tuscany by car is hard to beat.

If you can’t or won’t drive, Tuscany’s public transport is affordable and reaches the main sights, though buses to the smaller places can be infrequent. Only the bigger towns have train stations.

For each place below I’ve noted whether there’s a train station, or one within a short bus ride.

Bear the landscape in mind too. Many towns and villages sit on a hilltop, so even with a station nearby you may need a local bus, or a steep uphill walk, to reach the centre.

If you’re relying on public transport, base yourself in one of the larger towns and day trip to the smaller places, either independently or on an organised tour. I’ve used Florence and Siena as bases, and Pisa works well too.

Best Tuscan Cities (A to Z)

Arezzo

For a historic city off the main tourist trail, head to Arezzo.

This former Etruscan city is home to Piazza Grande, one of Italy’s finest squares. Stop for a coffee under the loggia that lines one side of it.

Arezzo is a Mecca for art and antique lovers. The biggest antiques fair in Italy sets up in Piazza Grande on the first weekend of every month.

The artist Giorgio Vasari lived here, and you can visit the palace he bought and decorated himself in 1540. The Church of San Francesco holds a Renaissance fresco cycle by Piero della Francesca, the Legend of the True Cross.

Arezzo is just one hour by train from Florence, making it an easy day trip.

Florence

Editor’s note: Florence is where I first fell in love with Italy, over 30 years ago now, and I’ve been back many times since. It’s also where I base myself for exploring the rest of Tuscany. If you only do one Tuscan city with a base, make it this one.

Florence, birthplace of the Renaissance, should not be missed on any trip to Tuscany. The red-tiled dome of the cathedral rises over the whole city.

If you enjoy great views, climb to the top of the Duomo Dome or Giotto’s bell tower. Art lovers should head to the Galleria dell’Accademia, home to Michelangelo’s David (one of the finest sculptures in Florence) and the Uffizi Galleries.

Do not miss the Ponte Vecchio, the bridge that spans the Arno, and the Pitti Palace nearby, one of Europe’s most beautiful palaces.

Beyond the famous landmarks, there are there are quieter corners worth seeking out. The Fra Angelico frescoes at the San Marco Monastery get far less attention than the Duomo, and are all the better for it.  

Suggested by Darcy of Plan, Ready, Go

Pisa

Editor’s note: I first saw the Leaning Tower on my first trip to Italy in my twenties, on a quick stop. I haven’t been back, and it’s on my list to correct that.

Pisa is one of the most visited and beautiful cities in Italy. Whilst many go there simply to visit the torre pendente (Leaning Tower), there is more to it than that.

Most people do Pisa as a day trip from Florence, but staying a night gives you time to see everything.

The Piazza dei Miracoli, where the Leaning Tower stands, is also home to the white marble cathedral, Santa Maria dell’Assunta. Once you’ve had your obligatory selfie, head into town.

Borgo Street is one of Pisa’s oldest, and the Ammannati House marks where Galileo Galilei was born in 1564. For something more recent, seek out Tuttomondo, a 180 square metre mural on the theme of peace, painted on the San Antonio Abate church

Suggested by Pamela of The Directionally Challenged Traveler

Sienna

Editor’s note: I first did Siena as a day trip, liked it enough to return for a longer stay. A day is enough to see the highlights, but staying overnight gets you the Campo without the crowds, early morning or after the coach parties leave.

Siena has one of the finest squares in Italy, the shell-shaped Piazza del Campo. 

Take a seat at one of the cafes on its edge and watch the world go by over a coffee or a glass of wine. Visit in July or August and you might catch the Palio di Siena, a horse race run around the piazza itself.

There is plenty more things to see in Siena. The Duomo di Siena is a medieval cathedral built in striped black and white marble, inside and out.

Go early or book online to skip the queues, then climb inside the dome to look down on the patterned floor. The cathedral’s museum, the Museo dell’Opera Metropolitana, and the Facciatone, a walkway on its roof, both give superb views over the city.

The other great viewpoint is the Torre del Mangia on Piazza del Campo. The 14th-century tower is 102 metres tall and looks out over the square, the cathedral and the rooftops beyond.

Suggested by James Ian of Travel Collecting

Best Tuscan Towns (A to Z)

Certaldo

Certaldo is a beautiful, off-the-beaten-path town in Tuscany, split between old and new. The old town sits on a hill, reached by funicular, and walking its streets feels like stepping back into the medieval period..

Certaldo is best known as Boccaccio’s home. Via Boccaccio, the main street, leads to the Palazzo Pretorio, once home to Florence’s vicars, and on to Boccaccio’s own house, where rare editions of his work are on display.

Look out for the small nails museum and the archery headquarters tucked into a cellar. If you’re there in June, the Dinner with Mr Boccaccio event turns one street into an outdoor medieval dining hall, with locals dressed in character.

Suggested by Joanna of The World in My Pocket

Cortona

Cortona was put on the map by Under the Tuscan Sun, the book and later the film. It’s in eastern Tuscany, about an hour’s drive from Florence.

This stone town dates back to 400 to 600 BC, though it flourished mainly from the 13th century. Its heart is Piazza della Repubblica, ringed by the town hall, clock tower and former palace. Visit on a Saturday, market day, to see it at its liveliest.

There is plenty to see and do in Cortona, from museums to churches, but it is just as good getting lost in its narrow lanes with a gelato from Gelateria Snoopy in hand, taking in the views over the valley.

Suggested by Renee of Dream Plan Experience

Greve

Greve in Chianti is on the scenic Chiantigiana road and has been settled since ancient times.

Start in the oddly shaped main square, Piazza Matteotti, best visited on a Saturday when the weekly market fills it with flowers, cheese and household goods. From there, take in the Basilica of Santa Croce, the Wine Museum and the Museum of Sacred Art, and stop for a meal at Ristorante Enoteca Fuoripiazza or Ristorante la Bottega del Moro.

Nearby wineries such as Azienda Agricola Montefioralle and Montecalvi offer tastings, and Greve hosts an antiques fair at Easter, a flower festival in May and the Chianti Classico wine festival in September.

Suggested by Or of My Path in the World

Lucca

Editor’s note: This was one of the most rewarding day trips I’ve done in Tuscany, out from Florence. Give yourself a full day if you can, the walls alone justify it.

Lucca is Tuscany’s unsung heroine, overshadowed by her popular neighbours but well worth a detour.

This is a walled city, and the walls themselves are one of the main draws. Converted into a park in the 18th century, you can walk or cycle the full loop for views over the town and the countryside beyond.

Lucca is also known for its medieval towers, especially Torre Guinigi, easy to spot thanks to the tree growing from its roof. The Piazza dell’Anfiteatro sits on the site of a Roman amphitheatre, and the Chiesa di San Michele in Foro looks down over the square that shares its name.

You could spend a couple of days here, and it also makes a good base for Pisa, Florence, the coast and the Garfagnana hills.

Suggested by Katy of Untold Morsels

Montepulciano

Perched on a hilltop in the Val d’Orcia, medieval Montepulciano is easy to reach from both Florence and Siena and makes a good stop on a Tuscany road trip.

The cobbled town is walkable with sturdy shoes and surrounded by the vineyards that produce Nobile di Montepulciano, one of Italy’s best wines. Head for Piazza Grande in the centre, where locals gather in the evening, and have dinner at Ristorante la Grotta near the Renaissance Church of San Biagio, which looks out over the countryside.

With a rental car, Montepulciano makes an easy base for day trips to Pienza, Montalcino and Siena.

Panzano

Panzano is a hilltop town in the Chianti Classico wine region, less than an hour’s drive from Florence, and a great addition to your Italy itinerary.

I’d recommend staying at Podere Felceto, a family-run organic olive oil farm with a traditional stone villa and an outdoor pool looking over the countryside.

Panzano has plenty of wine tasting on offer, with wineries such as Castello di Verrazzano nearby, and good places to eat. For For an intimate dinner, try Ristorante Oltre Il Giardino for meat and pasta dishes. For something livelier, book a table at Officina Della Bistecca, owned by the well-known butcher Dario Cecchini, where you’ll be served five courses of steak in a dining room above his shop.

Suggested by Cecily of Groovy Mashed Potatoes

Pienza

Pienza‘s historic centre is a perfect Renaissance town surrounded by rolling fields and cypress avenues. It’s been a UNESCO World Heritage site since 1996.

Wander through to find pretty squares, historic buildings and museums, including the town hall, the Palazzo Piccolomini and the Cathedral of Santa Maria Assunta. Take a break at one of the restaurants around the main square, Piazza Pio II, or tucked along the side streets, and try the local Pecorino cheese, which Pienza is known for.

Suggested by Jürgen and Martina of Places of Juma

Pitigliano

Almost halfway between Rome and Florence, Pitigliano sits on a flat cliff of tufa rock, surrounded by forest.

This volcanic landscape is part of the Tuscia region, once home to the Etruscan civilisation, whose culture and engineering shaped much of what the Romans later built on. Pitigliano looks medieval today, but look closer and you’ll find stores and houses dating back to the pre-Roman era.

The historic centre can be seen in a few hours. Start at Piazza Della Repubblica and the Fountain of the Seven Spouts, built into the old aqueduct, then the Orsini Fortress and its Archaeological Museum, and Via Roma with its artisan shops. From there you’ll reach Little Jerusalem, one of the oldest Jewish quarters in Europe.

If you like walking, the Vie Cave are worth seeking out: ancient paths cut into the tufa walls, crossing an Etruscan necropolis that includes the Tomb of Ildebranda.

Suggested by Lisa of Travel Connect Experience

Portoferraio

Portoferraio is the capital of the island of Elba and a good base for exploring more of Italy’s coast.

The name means iron harbour, a nod to its history as a trading port, though these days it’s better known as the place where Napoleon Bonaparte was exiled in 1814, and lived for almost a year.

Villa dei Mulini, one of Napoleon’s former homes, is the main draw, with plenty on his life and exile. The Martello Tower is worth a visit too, built originally as part of the island’s defences and later used as a prison. Climb it for a view over the bay.

Suggested by Emma of Emma’s Roadmap

Volterra

Volterra is a hilltop town overlooking the countryside, quieter than Pisa or Lucca, with roots going back to the Etruscans.

The best things to do in Volterra include visiting Piazza dei Priori and the Palazzo dei Priori on it, climbing the tower for the view. From there you can explore the remains of a Roman theatre, shop for alabaster or visit the Etruscan Museum.

Twilight fans might recognise Volterra from New Moon, though the film itself was shot in another Tuscan town, Montepulciano.

Suggested by Kate of Our Escape Clause

Best Villages in Tuscany

Monteriggioni

Monteriggioni sits on the outskirts of Siena with views over the Chianti hills. This walled medieval village has towers you can spot from miles off.

The walls are still intact, and you can walk along sections of them for €5, well spent for the 360 degree views. The Armoury Museum lets you try on armour and swing a 10kg sword, alongside reproduction medieval and Renaissance weapons.

Visit at the start of July for the Medieval Festival, when locals dress in period costume. It’s one of the best attended events in Tuscany.

San Gimignano

Editor’s note: I still remember the approach by bus, watching the towers appear on the skyline before reaching the town. That view alone made the trip for me.

Known as the Manhattan of Tuscany, San Gimignano is small enough to see in a day, with medieval towers and wide views over the surrounding hills.

It’s a classic Tuscan village, ringed by olive groves and vineyards, with narrow streets, several churches and viewpoints worth seeking out. It’s known for its food and wine too, with plenty of restaurants and shops to try both.

Of the original 72 towers, fourteen survive. The tallest, Torre Grossa, reaches 54 metres and is open to climb.

San Quirico d’Orcia

You may not know the name San Quirico d’Orcia, but you’ve likely seen photos of its Chapel of Madonna di Vitaleta, ringed by cypress trees on rolling hills.

It sits in the Val d’Orcia, midway between Pienza and Montalcino, less than an hour’s drive from Siena. The walled village can be explored in a day.

One main street runs through the centre, past the Collegiata di San Quirico and the Church of Santa Maria Assunta, whose rose garden leads into the Horti Leonini Gardens, a formal Italian garden.

Once you’ve seen the town, walk up to the chapel or out into the surrounding countryside. Il Rigo Agrotourism, a stone farmhouse nearby, makes a good base, serving delicious regional Italian dishes, including an organic breakfast and a four course dinner at a fair price.

Suggested by Denise of Chef Denise

Which of These Places in Tuscany Will You Visit?

One of the things that Italy is famous for is its medieval settlements, and you now have a solid list of towns and villages in Tuscany to work from.

Whether you picture yourself with an espresso or a glass of Chianti in a piazza, or wandering through a Renaissance church, you cannot make a bad choice.

Buon viaggio!

About Bridget

Bridget Coleman has been a passionate traveller for more than 30 years. She has visited 70+ countries, most as a solo traveller.

Articles on this site reflect her first-hand experiences.

To get in touch, email her at hello@theflashpacker.net or follow her on social media.

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