What to See in the Province of Siena: A Complete Guide

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The province of Siena, located in the heart of Tuscany, is a region rich in history, culture, and natural beauty. Every corner of this province offers something unique and fascinating, from medieval villages to rolling hills, from famous vineyards to historical sites. This guide will accompany you through the main attractions of the province of Siena to help you plan an unforgettable trip.

1. Siena

Piazza del Campo: The beating heart of the city, this shell-shaped square is famous for the Palio, a horse race held twice a year. The square is surrounded by historic buildings, including the Palazzo Pubblico and the Torre del Mangia, which offers a spectacular view of the city and the surrounding countryside.

Siena Cathedral (Duomo): This Gothic cathedral is one of the masterpieces of Italian architecture. Inside, you will find works of art by Michelangelo, Donatello, and Bernini, as well as the magnificent marble floor, composed of 56 panels depicting biblical and allegorical stories.

Museo dell’Opera Metropolitana: Located next to the Cathedral, this museum houses a collection of sacred art, including works by Duccio di Buoninsegna and other Sienese masters. Don’t miss Duccio’s “Maestà,” a masterpiece of Gothic painting.

Santa Maria della Scala: An ancient hospital turned museum complex, it is one of the oldest hospitals in Europe and today hosts both temporary and permanent exhibitions. Its collections range from archaeology to contemporary art, and it also tells the history of healthcare.

2. San Gimignano

Towers of San Gimignano: Known as the “Manhattan of the Middle Ages,” San Gimignano is famous for its medieval towers. Once there were 72, today 14 remain, offering breathtaking panoramic views of the surrounding countryside. Each tower tells the story of a noble family of the city.

Collegiata di Santa Maria Assunta: The main church of San Gimignano, famous for its well-preserved frescoes depicting biblical scenes. The frescoes by Benozzo Gozzoli and Taddeo di Bartolo are particularly noteworthy.

Museo Civico and Torre Grossa: Located in the Palazzo del Popolo, the museum houses a collection of local art and artifacts. The Torre Grossa, the highest tower in the city, offers a spectacular view and a unique perspective on the smaller towers.

3. Montepulciano

Piazza Grande: The historic center of Montepulciano is dominated by this square, surrounded by Renaissance buildings such as the Palazzo Comunale and the Cathedral of Santa Maria Assunta. The square is the hub of local celebrations and events.

Historic Cellars: Montepulciano is famous for its wine, Vino Nobile di Montepulciano. Visit the underground cellars to taste some of the best wines in the region and discover the secrets of Tuscan winemaking.

Temple of San Biagio: Located just outside the city walls, this Renaissance masterpiece is surrounded by the Tuscan countryside and offers an enchanting view. Designed by Antonio da Sangallo the Elder, the temple is an extraordinary example of Renaissance architecture.

4. Montalcino

Fortress of Montalcino: This medieval fortress offers a panoramic view of the surrounding hills and hosts events and wine tastings, particularly the famous Brunello di Montalcino. Its massive walls and crenellated towers are perfectly preserved.

Abbey of Sant’Antimo: Located in a quiet valley near Montalcino, this Romanesque abbey is one of the most evocative places in the province. Founded in the 8th century, the abbey is famous for its Gregorian chants performed by the monks.

Civic and Diocesan Museum: Houses a collection of sacred art and local artifacts, offering an insight into the history and culture of Montalcino. Among the most important works are paintings from the Sienese school and wooden sculptures.

5. Val d’Orcia

Pienza: This small Renaissance town is known for its central square, designed by Pope Pius II, and for its pecorino cheese. Visit the Cathedral and Palazzo Piccolomini for a dive into the Renaissance and stroll through the quiet streets of the historic center.

Bagno Vignoni: Famous for its central square, which is a thermal pool, Bagno Vignoni is a perfect place to relax and enjoy the thermal waters. The village is an oasis of peace and wellness.

Chapel of the Madonna di Vitaleta: This small chapel, located on a hill between Pienza and San Quirico d’Orcia, is one of the most photographed places in Tuscany. Its simple charm and secluded position make it a perfect subject for photographers.

6. Chianti Senese

Castellina in Chianti: A picturesque village with a medieval fortress and an archaeological museum that offers an overview of the Etruscan and Roman history of the region. The historic center is a labyrinth of alleys and small squares.

Radda in Chianti: This medieval village offers winding streets, panoramic views, and numerous wineries where you can taste the famous Chianti Classico. The Palazzo del Podestà, with its noble coats of arms, is one of the main attractions.

Gaiole in Chianti: Visit the Castello di Brolio, a historic fortress that offers wine tastings and a spectacular view of the surrounding countryside. The castle has a long history linked to the Ricasoli family.

7. Colline Metallifere

Massa Marittima: A charming village with a splendid Romanesque cathedral, the Duomo di San Cerbone, and a mining museum that tells the story of mining in the region. The mines played a crucial role in the economic development of the village.

Technological and Archaeological Park of the Colline Metallifere: This park offers hiking trails, guided tours of the mines, and educational workshops, perfect for families and history enthusiasts. The area is rich in evidence of Etruscan and Roman mining activities.

8. Crete Senesi

Asciano: A small village with the Civic Archaeological and Sacred Art Museum, which houses a collection of Etruscan artifacts and sacred art. The Church of Sant’Agostino and the Basilica of Sant’Agata are must-see stops.

Abbey of Monte Oliveto Maggiore: A magnificent monastic complex located among the hills of the Crete Senesi, famous for its frescoes and the tranquility of the place. Founded in 1313, the abbey is still inhabited by Benedictine monks.

San Giovanni d’Asso: Known for its Truffle Museum, where you can learn everything about the white and black truffles of the region. The village also hosts a very popular truffle festival in the autumn.

9. Rapolano Terme

San Giovanni Terme and Terme Antica Querciolaia: These spas offer a wide range of wellness treatments and thermal pools immersed in the beautiful Tuscan countryside. The thermal waters are renowned for their healing properties.

Museum of the Ancient Grange and Olive Oil: Located in an ancient grange, the museum tells the history of olive oil and agricultural production in the area. It is an interesting stop for those who want to learn about local agricultural traditions.

10. Monteriggioni

Castle of Monteriggioni: This fortified village, with its intact walls and towers, looks like it has come straight out of a history book. Walk along the walls to enjoy a panoramic view of the surrounding countryside.

Monteriggioni in Arme Museum: A museum dedicated to military history and medieval armor, perfect for history enthusiasts and families.


The province of Siena is a place of extraordinary beauty and cultural richness. Every city and village offers a unique combination of history, art, and breathtaking landscapes. Whether you are wine lovers, history buffs, or simply looking for a place to relax and enjoy life, the province of Siena has something for everyone. Plan your trip carefully to ensure you don’t miss any of the wonders this fascinating region has to offer. Whether it’s exploring ancient villages, tasting fine wines, or relaxing in the thermal baths, Siena and its province will offer you an unforgettable experience.

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