Siena and San Gimignano Tour | Private

This tour offers the perfect opportunity to explore two of Tuscany’s most stunning medieval towns. Admire the architecture spread throughout the seemingly cinnamon-sprinkled city of Siena before moving on to San Gimignano to explore the perfectly preserved town of the 14 towers.

After taking this private tour from Rome or Florence, you’ll feel you’ve fully explored the treasures of Tuscany’s lush and rolling countryside, experiencing the real side of rural Italy as you acquaint yourself with two of its most charming settlements.

Explore the winding streets of Siena

The first stop on your private Siena and San Gimignano tour is the medieval city of Siena, a fierce rival of Florence in the past and, to some extent, in the present. Siena was one of Italy’s leading city states throughout the Middle Ages, booming because of its still existent bank – Monte dei Paschi di Siena.

Wander the historic center’s contradas, the boroughs in which Siena is divided, and learn all the stories surrounding the famous Palio, a horseracing event dating back centuries and still held twice a year on July 2nd and August 16th in Siena’s Piazza del Campo.

Visit Siena’s Piazza del Campo, Duomo, and Church of San Francesco

Explore Siena’s Piazza del Campo, described by French philosopher Michel de Montaigne in the 16th century as the most beautiful in Italy, and marvel at its imposing bell-tower which looms out over the square.

Step inside the 13th-century Basilica of San Domenico, an incredible architectural achievement built on the slopes of the Sienese hillside. As well as housing an enviable collection of Tuscan artworks, the basilica is home to the relics of Saint Catherine of Siena – one of Italy’s two patron saints, the other being Saint Francis of Assisi.

Your final stop in Siena is the Duomo, whose beauty easily rivals that of its Florentine equivalent. Consecrated in 1215, it manifests one of the best examples of Italian Gothic and Romanesque architecture and boasts artworks by Bernini within.

Indulge in a traditional lunch at a local restaurant

For lunch, we will suggest one of Siena’s most reputed local trattorie, where you can linger over a long lunch accompanied by fine local wines, originating from the Sienese region or nearby Chianti or Val d’Orcia.

Meat is particularly popular across Tuscany, especially bistecca (beef steak) wild-boar based ragù. Yet the variety of culinary delights on offer caters to all tastes. Just make sure to try pici alla senese, the area’s beloved pasta, consisting of thick tubes of spaghetti coated in a mouthwatering meat sauce.

Continue on to San Gimignano, another jewel in Tuscany’s medieval crown

With your private driver you’ll then journey through the rolling hills of the Sienese countryside until you reach the towered town of San Gimignano. No town encapsulates medieval Tuscany like San Gimignano. Its state of perfect preservation owes not to its strength but to its weakness – for it was only the complete capitulation of its nobility in the 14th century (and an unfortunate spate of the Black Death) that saved the settlement from destruction.

The key to appreciating the enchanting town of San Gimignano is to take it slowly. Duck into the Collegiata to admire its breathtaking frescoes, indulge yourself with a gelato in the town square, and treat yourself to a glass of Vernaccia di San Gimignano wine – the product that’s made the town famous.

Having experienced the true Tuscany, your private driver will take you back through the rolling hills of the Italian hinterland to your accommodation in Rome or Florence.