Private Tuscany Day Trip from Florence with Siena and Monteriggioni

Pisa and the Square of Miracles

The day starts with the drive west to Pisa, about an hour from Florence. In the green lawns of the Piazza dei Miracoli, the Square of Miracles, stand the cathedral, the round Baptistery and the famous bell tower, a group of white marble buildings from the eleventh to the fourteenth centuries that forms a UNESCO World Heritage Site.

The Leaning Tower began to tilt soon after construction started in 1173, because the ground beneath it is soft, and it was stabilised by engineers around the year 2000. It stands about fifty-six metres tall and can be climbed with a timed ticket, not included in the tour. Is Pisa worth visiting just for the tower? On a private Tuscany tour you can see it in an hour without a separate trip.

San Gimignano and its medieval towers

From Pisa your driver-guide heads inland to San Gimignano, whose stone towers rise over the Elsa valley. The town grew rich in the Middle Ages from trade and from pilgrims on the road to Rome, and its leading families built tall tower houses to show their power; the ones still standing give it one of the most recognisable skylines in Italy and a place on the UNESCO list.

San Gimignano is a natural stop for lunch, and you can wander the triangular Piazza della Cisterna with its old well, Piazza del Duomo with the town hall and the Torre Grossa, and the garden of the ruined fortress for views over the hills. Halal food is limited here, but vegetarian dishes, pasta and the town's famous ice cream are easy to find.

Monteriggioni, the walled village

A short drive south brings you to Monteriggioni, one of the most complete walled villages in Italy. Siena built it between 1213 and 1219 as a frontier fortress on a small hill facing Florentine territory, and its ring of walls and square towers still encircles the village almost intact, looking from the road like a stone crown on the hilltop.

Inside the gate there is a single main square with a Romanesque church, a few houses and craft shops, and sections of the walls can be walked for views over the countryside. It takes only thirty to forty-five minutes to see, which is why it fits so neatly into a private day trip from Florence. Monteriggioni also lies on the old pilgrim road to Rome.

Siena, Piazza del Campo and the cathedral

Only twenty minutes further on lies Siena, once Florence's great rival and today one of the best preserved medieval cities in Europe. Its streets converge on Piazza del Campo, the sloping, shell-shaped square in front of the brick Palazzo Pubblico and the tall Torre del Mangia, where the Palio horse race is run on 2 July and 16 August.

Up the hill, Siena Cathedral is striped in white and dark green marble and famous for its inlaid marble floor and the colourful Piccolomini Library. Your driver-guide explains the city as you explore and helps you decide whether to enter the cathedral; tickets are not included. How long to spend in Siena? On this day trip about two hours, enough for the Campo and the cathedral square.

The Chianti hills on the way back

The return to Florence crosses the Chianti, the classic Tuscan landscape of rolling hills, olive groves, oak woods and cypress-lined drives leading to stone farmhouses and castles. Villages such as Castellina and Greve sit along these routes, and the light in the late afternoon makes this the most beautiful part of the drive.

With a private driver you can stop at a viewpoint for photographs whenever you wish. The best time to visit Tuscany for this kind of day is from April to June and in September and October, when the weather is mild and the hills are green or golden. You arrive back in Florence in the evening, about nine hours after departure.