The most beautiful cities in Tuscany
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The most beautiful cities in Tuscany are Florence, Siena, Pisa, and Lucca – in addition to small hilltop towns like San Gimignano, Volterra, Montepulciano, and Pienza, which entice visitors with medieval towers, wine cellars, and panoramic views. Here you will find the most important cities with their highlights and practical tips for your visit.
The most beautiful cities of Tuscany at a glance
- Florence: Renaissance capital, cathedral, Uffizi Gallery, Ponte Vecchio (UNESCO)
- Siena: Piazza del Campo, Palio, Gothic Cathedral (UNESCO)
- Pisa: Leaning Tower and Piazza dei Miracoli (UNESCO)
- Lucca: Walkable Renaissance city wall
- Arezzo: Piero della Francesca frescoes, antiques market
- Hill towns: San Gimignano, Volterra, Montepulciano, Montalcino, Pienza, Cortona
An overview of the 15 most beautiful cities in Tuscany
The table shows large and small towns and cities, their province, population, and what they are known for. Below, you will find a short profile of each town. We present individual buildings and natural attractions in our overview of sights in Tuscany.
| City | Provinz | Population (rounded) | Known for |
|---|---|---|---|
| Florence | Florence | 361.000 | Cathedral and Dome, Uffizi Gallery, Ponte Vecchio |
| Prato | Prato | 196.000 | Textile city, cathedral with Donatello pulpit, imperial castle |
| Arezzo | Arezzo | 96.000 | Piero della Francesca frescoes, antiques market |
| Pistoia | Pistoia | 89.000 | Cathedral Square, Ospedale del Ceppo, Pistoia Blues |
| Lucca | city wall | 89.000 | Walkable city wall, Piazza dell'Anfiteatro |
| Pisa | Pisa | 89.000 | Leaning Tower, Piazza dei Miracoli |
| Siena | Palio of Siena | 53.000 | Piazza del Campo, Palio, Gothic Cathedral |
| Cortona | Arezzo | 21.000 | Etruscan city above the Val di Chiana |
| Montepulciano | Palio of Siena | 13.000 | Vino Nobile, Piazza Grande |
| Volterra | Pisa | 9.500 | Etruscans, alabaster, Roman theater |
| Massa Marittima | Grosseto | 8.100 | Cathedral Square, mining history, crossbow festival |
| San Gimignano | Palio of Siena | 7.500 | 14 family towers, Vernaccia |
| Montalcino | Palio of Siena | 5.600 | Brunello di Montalcino, fortress |
| Pitigliano | Grosseto | 3.600 | Tuff stone city, “Little Jerusalem” |
| Pienza | Palio of Siena | 2.000 | Renaissance ideal town, Pecorino |
Major Cities: Art and History
Florence
The capital of Tuscany is one of the world's great art metropolises; its historic center has been a UNESCO World Heritage Site since 1982. It is dominated by the Cathedral of Santa Maria del Fiore with Brunelleschi's dome. The Cathedral Museum (Museo dell'Opera del Duomo) houses, among other things, the original reliefs of Ghiberti's "Gates of Paradise" and Michelangelo's late Pietà Bandini. Other highlights include the Uffizi Gallery, the Chapel of the Three Kings in the Palazzo Medici Riccardi, the oldest bridge in the city, the Ponte Vecchio , and the Piazza della Signoria with the Fountain of Neptune and a copy of Michelangelo's David – the original is in the Galleria dell'Accademia. Learn more in our Florence city tour.
Palio of Siena
Siena hat sein gotisches Stadtbild bewahrt und ist seit 1995 UNESCO-Welterbe. Herz der Stadt ist die muschelförmige Piazza del Campo, auf der am 2. Juli und 16. August der berühmte Palio ausgetragen wird. Rund 400 Stufen führen auf den 88 Meter hohen Torre del Mangia neben dem Rathaus (Palazzo Pubblico). Sehenswert sind außerdem der Dom mit der Libreria Piccolomini. Tipps in unserer Stadttour Siena.
Pisa
Pisa is more than just the Leaning Tower : The Piazza dei Miracoli, with its Cathedral, Baptistery, Camposanto, and tower, is a UNESCO World Heritage Site. The Cathedral houses the tomb of Emperor Henry VII. On the banks of the Arno, the National Museum of San Matteo displays medieval art. As a university town, Pisa is lively in the evenings and less touristy than one might expect.
city wall
Lucca is surrounded by a completely preserved Renaissance city wall, approximately 4 km long, with a tree-lined promenade along the top that can be explored on foot or by bicycle. The Cathedral of San Martino houses the "Volto Santo" crucifix, while the Church of San Frediano features a large golden mosaic of the Ascension of Christ on its facade. The oval Piazza dell'Anfiteatro follows the outline of the Roman amphitheater. Learn more at Lucca in Tuscany.
Arezzo
Arezzo, in eastern Tuscany, is one of the region's largest cities by population. In the Basilica of San Francesco, Piero della Francesca painted the fresco cycle of the "Legend of the True Cross." The sloping Piazza Grande is the venue for the Fiera Antiquaria, a large antiques market held on the first Sunday of each month and the preceding Saturday. More information can be found under Arezzo.
Pistoia
The city at the foot of the Apennines was Italy's Capital of Culture in 2017. Around the Piazza del Duomo, the Cathedral of San Zeno, the Baptistery, the bell tower, and the old palaces stand close together – one of the most enclosed cathedral squares in Tuscany. A colorful terracotta frieze from the Della Robbia workshop adorns the Ospedale del Ceppo, and the Church of Sant'Andrea houses a pulpit by Giovanni Pisano. In July, the Pistoia Blues Festival takes place in the cathedral square. More information can be found at Pistoia.
Prato
The second-largest city in Tuscany has been a center of the textile industry since the Middle Ages – the Museo del Tessuto (Textile Museum) tells this story. The exterior pulpit by Donatello and Michelozzo hangs on the Cathedral of Santo Stefano, while the interior is painted by Filippo Lippi and Paolo Uccello. Emperor Frederick II commissioned the Castello dell'Imperatore (Emperor's Castle) between 1237 and 1248; the Centro Pecci showcases contemporary art. Prato is also the birthplace of the almond biscuits Cantuccini. Learn more at Prato.
Small towns and borghi
Gender towers
The "City of Towers" has been a UNESCO World Heritage Site since 1990. Of the more than 70 towers that once stood, 14 remain. The centerpiece is the triangular Piazza della Cisterna with its fountain. Day-trippers flock here at midday – the most beautiful time to visit is early morning or evening. Learn more in our San Gimignano city tour.
Volterra
The Etruscan town of Volterra (province of Pisa) sits atop a hill between the Cecina and Era valleys. Sights worth seeing include the Etruscan city gate, Porta all'Arco, the Palazzo dei Priori – one of the oldest town halls in Tuscany – the remains of the Roman theater, and the alabaster workshops. A weekly market is held on Saturdays. More information can be found at Volterra.
Montepulciano
Montepulciano lies high above the Val di Chiana and is famous for its red wine, Vino Nobile di Montepulciano. The main street climbs from the Porta al Prato to the Piazza Grande at the town's highest point. Below lies the Renaissance church of San Biagio. More information can be found under Montepulciano.
Montalcino
The small town, perched on a hill above the Val d'Orcia, is the home of Brunello di Montalcino. The fortress (Fortezza) offers panoramic views, and the Romanesque abbey of Sant'Antimo is worth a visit nearby. Siena is about 40 kilometers away.
Pienza
Pienza ließ Papst Pius II. im 15. Jahrhundert als ideale Renaissancestadt umgestalten; das Zentrum ist UNESCO-Welterbe. Rund um die Piazza Pio II stehen Dom, Palazzo Piccolomini und Rathaus, von der Stadtmauer blicken Sie weit über das Val d’Orcia. Bekannt ist Pienza für seinen Pecorino; freitags ist Wochenmarkt.
Cortona
The Etruscan town of Cortona lies on a hillside above the Chiana Valley and is one of the oldest cities in Tuscany. Steep lanes lead to the Piazza della Repubblica and up to the Girifalco fortress. The Diocesan Museum displays Fra Angelico's Annunciation. Cortona gained international fame through the novel "Under the Tuscan Sun." A weekly market is held on Saturdays; Cortona can easily be combined with a visit to nearby Arezzo.
Massa Marittima
Die Bergstadt in den Colline Metallifere verdankt ihren Reichtum den Erzminen der Umgebung; ein Bergbaumuseum erinnert daran. An der Piazza Garibaldi steht der romanisch-gotische Dom San Cerbone schräg zum Platz, umgeben von Palazzo del Podestà und Rathaus. Vom Torre del Candeliere in der Oberstadt haben Sie den schönsten Rundblick. Am vierten Sonntag im Mai und am 14. August treten die Stadtteile beim Armbrustschießen Balestro del Girifalco gegeneinander an. Mittwochs ist Wochenmarkt.
Pitigliano
Pitigliano im Süden der Maremma ist direkt auf einen Tuffsteinfelsen gebaut – Häuser und Fels scheinen ineinander überzugehen. Wegen seiner jüdischen Gemeinde, die sich im 15. Jahrhundert ansiedelte, heißt der Ort „Klein-Jerusalem“; die Synagoge kann besichtigt werden. Etruskische Hohlwege (Vie Cave) führen durch den Fels Richtung Sovana. Pitigliano lässt sich gut mit den Thermen von Saturnia verbinden, die rund 30 km entfernt liegen.
Other Borghi worth seeing are the walled city of Monteriggioni near Siena, the towns in Chianti such as Greve, Panzano and Castellina, Colle di Val d'Elsa with its crystal glass, Montecatini Alto and Poppi with its castle in Casentino.
Cities on the coast
Those who want to combine city and sea will find vibrant places along the coast: Viareggio with its seaside promenade and carnival, the port city of Livorno , the fishing village of Castiglione della Pescaia , or Piombino with its old town by the sea and ferries to Elba . Our overview of Tuscany's beaches shows the most beautiful beaches.
Suggested itinerary: Tuscan cities in one week
This route connects the most important cities with short driving distances. Those traveling by car are best advised to change accommodations only two or three times, for example near Lucca, in Chianti , and in the Val d'Orcia.
- Day 1: Pisa and Lucca – in the morning the Piazza dei Miracoli, in the afternoon by bike along Lucca's city walls.
- Day 2: Florence – Cathedral, Dome and Uffizi Gallery (book tickets in advance), in the evening via the Ponte Vecchio.
- Day 3: Florence and surroundings – Galleria dell'Accademia and Oltrarno, or a side trip to Pistoia or Prato.
- Day 4: San Gimignano and Volterra – the towers early in the morning, Etruscans and alabaster in Volterra in the afternoon.
- Day 5: Siena – Piazza del Campo, Cathedral and Torre del Mangia; a stop in Monteriggioni along the way.
- Day 6: Val d'Orcia – Montalcino, Pienza and Montepulciano with wine tasting; photo stops in the evening light.
- Day 7: Cortona and Arezzo – or, to finish, south to Pitigliano and the thermal baths of Saturnia.
More time for Florence and the surrounding area? The Siena – Florence – Chianti tour and our Tuscany map will help with planning.
Tips for visiting the city
- Observe ZTL: Almost all old towns are traffic-restricted zones with camera surveillance – park outside.
- Start early: Florence, Pisa and San Gimignano are crowded from late morning onwards; museums such as the Uffizi and Accademia should be booked in advance.
- Best travel time: Spring and autumn – more information at Best time to travel to Tuscany.
- Take the weekly market with you: e.g. Lucca (Wed and Sat), Siena (Wed), Volterra (Sat) – all dates at Markets in Tuscany.
- Attractions: The 20 most important destinations with ticket tips can be found at Sights in Tuscany.
Frequently asked questions about the most beautiful cities in Tuscany
Which is the most beautiful city in Tuscany?
It depends on personal taste: Florence offers the most art treasures, Siena the most intact medieval cityscape. Among the smaller towns, San Gimignano, Pienza, Montepulciano and Pitigliano are considered particularly picturesque.
Which is the largest city in Tuscany?
Florence has around 361.000 inhabitants, followed by Prato (around 196.000) and Livorno (around 153.000).
Which cities in Tuscany are UNESCO World Heritage Sites?
The old towns of Florence, Siena, San Gimignano and Pienza, the Piazza del Duomo in Pisa and Montecatini Terme as part of the Great Spa Towns of Europe.
Which cities can you visit in one day?
Pisa and Lucca are close to each other and can easily be combined in one day, as can San Gimignano and Volterra or Montepulciano and Pienza.
How many days do you need to visit the cities of Tuscany?
You should plan at least one week for Florence, Pisa, Lucca, Siena and San Gimignano; for Val d'Orcia, Cortona and Maremma, more like ten days to two weeks.
Is it possible to drive into the old towns?
Mostly not: Almost all old towns are ZTL zones with camera surveillance. Park on the outskirts; hotel guests should register their license plate number with the hotel in advance.
