Private Siena and San Gimignano : Day Trip From Florence

On your Tuscany private tour, explore the charming streets and piazzas of San Gimignano, including hidden alleyways and local art studios, wine bars, and restaurants that showcase the town’s rich culture.

Visit Piazza del Duomo, the town's political and religious heart, and marvel at the 12th-century frescoes in the Collegiata, including Taddeo di Bartolo’s Last Judgement. Other works include Bartolo di Fredi’s The Creation of the World and Ghirlandaio’s Life of Santa Fina, masterpieces of Tuscan art.

Nearby, Piazza della Cisterna, with its ancient well, retains a medieval character, surrounded by some of the oldest and most beautiful buildings in the city.

End your tour with a visit to the Rocca, the fortress offering breathtaking panoramic views of the town, the countryside, and the rolling hills of Tuscany.

The skyline of San Gimignano is instantly recognisable, characterised by rows of magnificent medieval towers. During the 13th century rich lords moved to the town from the countryside and constructed these imposing towers throughout San Gimignano, as a symbol of their power and wealth. These towers were their private residences, casting a shadow over the less well-to-do citizens of San Gimignano. Only 13 of the 72 original towers are still standing, but these evocative monuments offer a key to understanding the social hierarchies of medieval society.

San Gimignano was an anonymous little town until the 11th century, when its location on the Via Francigena began to attract new kinds of visitors. The Via Francigena is a route of pilgrimage from Canterbury to Rome, still in use today. The road was used not only by pilgrims on their way to Rome, but also by an increasing number of merchants, and other long-distance travellers, who stopped off at San Gimignano to do business. The town began to flourish as a centre of saffron and mulberry cultivation, while the production and exportation of Vernaccia, the local white wine, helped the town to grow in size and wealth.

In San Gimignano you’ll learn more about this period of prosperity, and about the daily lives of the town’s inhabitants, as well as the decline in the 15th century. The remaining towers are a poignant symbol of a golden age that could not last forever.

A private tour of Siena is the perfect way to uncover the city’s secrets, exploring the churches, piazzas and alleyways of this spectacular medieval city. From the grandeur of its main square to the subtle charm of its backstreets, Siena never ceases to enchant its visitors. Your personal guide will take you on a journey through Siena’s history, discovering artistic masterpieces and stunning panoramas along the way.

The most famous of Siena’s squares is the extraordinary Piazza del Campo. Located in the very heart of the city centre, this shell-shaped square is encircled by elegant palazzi, and is widely regarded as one of the greatest medieval squares in Europe. It has been the centre of Siena’s public life for centuries, and it once played an important political role, as the location of the grand Palazzo Pubblico and the Torre del Mangia. On your Siena tour you’ll stroll through the piazza, admiring its architecture while learning about the politics and commerce of the medieval city.

From Piazza del Campo it’s a short walk to the second most famous square in Siena, the Piazza del Duomo. The square is dominated by the imposing 13th century cathedral, which has a striking facade of black and white marble. Black and white are the traditional colours of Siena, and the origin of this tradition has an intriguing connection with the myths and legends of the city’s foundation, as you’ll discover on your tour.

As well as learning about the rich history of Siena, you’ll also have the opportunity to study its architecture and admire the beauty of its artistic treasures. On your visit to the Duomo you’ll discover that seemingly every inch of the cathedral is filled with masterpieces, from the bronze sculpture of St John the Baptist by Donatello to a statue by the young Michelangelo. There are also works by Bernini, and various masterpieces of medieval and Renaissance art. The vibrant frescoes of the Piccolomini Library are particularly impressive, and on your Siena private tour you’ll learn about these beautiful artworks in their historical context, enriching your appreciation.

Your day trip in Tuscany will end with a short walk to the Basilica of San Domenico, which watches over the town from the top of the hill. This enormous church was built in the 13th century and subsequently enlarged, incorporating many features of Gothic architecture. After exploring the vast, atmospheric interior of the church and seeing the relics of St Catherine, you’ll step outside to enjoy panoramic views of the countryside - the perfect end to your Tuscan journey.

Siena prospered in the Middle Ages, partly due to its location on the Via Francigena. It became a center for money-lending and the wool trade, thriving in commerce and culture. The city-state, governed by noble families, also founded one of Italy’s oldest universities in 1240, fostering its educational reputation.

Siena reached its peak in the early 14th century, with a population of 50,000 and a booming economy. However, the devastating plague of 1348 led to a long period of decline.

In the 17th century, the introduction of the Palio by the Medici family revived Siena’s traditions, transforming the city’s atmosphere. The revival of festivals allowed Siena to embrace its unique history, cementing its place as one of Italy’s most beautiful and culturally significant cities.