Private Siena and San Gimignano Day Trip from Florence

Through the Chianti hills by private van

Leaving Florence in the morning, your private van heads south into the Chianti, the countryside of gentle hills between Florence and Siena. Narrow roads wind past silver olive groves, stone farmhouses and avenues of cypress trees, while medieval castles and fortified hamlets watch from the ridges, reminders of the centuries when the two cities fought over this border land.

On a private Tuscany day trip you can ask your driver to pull over wherever the view is best, something a large coach cannot do. Your tour leader explains the history of the villages and the farming life of the hills as you go. In autumn the olive harvest colours the landscape, and in spring the fields are bright green and full of wild poppies.

San Gimignano and its medieval towers

San Gimignano stands on a hilltop above the Elsa valley, its stone towers rising over the walls like a medieval skyline. In the twelfth and thirteenth centuries the town prospered from trade and from the pilgrim road to Rome, and powerful families competed to build the tallest tower houses. Many have fallen, but those that remain make it one of the most photographed towns in Italy and a UNESCO World Heritage Site.

Is San Gimignano worth visiting? Absolutely: few places keep their medieval streets so intact. During your free time you can climb the Torre Grossa, the tallest tower, step into the frescoed Collegiate Church or simply wander the lanes. Your tour leader suggests a route that fits the time and your interests.

Piazza della Cisterna and the Rocca di Montestaffoli

The main lanes lead to Piazza della Cisterna, a triangular square paved with bricks and centred on a thirteenth-century stone well, surrounded by tower houses and old palaces. A few steps away, Piazza del Duomo gathers the town hall, the tallest tower and the Collegiate Church, the political and religious heart of the medieval town.

For a sweeping view, climb up to the Rocca di Montestaffoli, the ruins of a fourteenth-century fortress whose garden overlooks the valley. San Gimignano is also known for its ice-cream shops and for craft shops selling ceramics and local saffron. How long to spend here? About two hours is enough for the main sights, which is why it pairs so well with Siena in one day.

Siena and Piazza del Campo

Many visitors ask how to get to Siena from Florence: by road it is about an hour, and a private Siena tour from Florence lets you combine it with San Gimignano without changing buses. Siena's historic centre is a UNESCO World Heritage Site, and its streets all lead down to Piazza del Campo, the sloping, shell-shaped square in front of the Palazzo Pubblico.

The brick town hall and its slender Torre del Mangia, more than one hundred metres tall, have watched over the square since the fourteenth century. Twice a year, on 2 July and 16 August, the Campo hosts the Palio, the bareback horse race between the city's districts. Your leader can point you to the best spots for photographs and a relaxed break.

Siena Cathedral and the contrade

Up the hill from the Campo, Siena Cathedral dazzles with its striped white and dark green marble and its carved Gothic façade. Inside, the inlaid marble floor, the pulpit and the Piccolomini Library with its bright frescoes are among the great sights of Tuscany. Tickets are not included, so you decide during your free time whether to go in; allow about an hour.

Around the cathedral and the Campo, the city is divided into contrade, historic districts with their own colours, emblems and fountains. The best time to visit Siena and San Gimignano is from April to June and in September and October, when the weather is mild. In the late afternoon your van brings you back to Florence in about an hour and a half.