San Gimignano and Siena Day Trip from Florence with Free Time

The Chianti hills between Florence and Siena

The road south from Florence crosses the Chianti, the stretch of countryside that most people picture when they think of Tuscany. Low hills are covered with olive groves and woods of oak, lines of cypress trees lead up to stone farmhouses, and fortified villages and castles stand on the ridges, many of them dating from the long medieval rivalry between Florence and Siena.

From the coach window the landscape changes with the seasons: bright green in spring, golden fields in summer and warm russet colours in autumn, when the olive harvest begins. The first leg to San Gimignano takes about 80 minutes, and the GPS audio guide tells the story of the villages and the hills along the way, so the journey itself becomes part of this Tuscany day trip from Florence.

San Gimignano, the town of towers

San Gimignano rises on a hill above the Elsa valley, its skyline of tall stone towers visible from far away. In the Middle Ages the town grew rich from trade and from pilgrims on the road to Rome, and rival families built ever higher tower houses to show their power. Many more towers once stood here; the ones that survive give the town its unmistakable profile, and its historic centre is a UNESCO World Heritage Site.

Is San Gimignano worth visiting? Few places in Italy keep their medieval look so completely. With your free time you can climb the Torre Grossa, the tallest tower, for a view over the hills, and visit the frescoed Collegiate Church on Piazza del Duomo. Our San Gimignano day trip from Florence gives you about two and a half hours here, enough for the main sights and a slow stroll.

Piazza della Cisterna and the viewpoints of San Gimignano

The heart of the town is Piazza della Cisterna, a sloping triangular square paved in brick and herringbone patterns, with an old stone well at its centre that once supplied water to the whole town. Tower houses and medieval palaces close it on every side, and the square leads straight into Piazza del Duomo, the civic and religious centre.

For the best panorama, walk up to the Rocca di Montestaffoli, the remains of a fourteenth-century fortress whose garden opens onto the valley and the rolling hills. The lanes of Via San Giovanni and Via San Matteo link the town gates to the squares and are lined with craft shops and ice-cream makers. Most visitors find that the morning, before the larger groups arrive, is the best time to explore.

Siena and Piazza del Campo

After a 40-minute drive the coach reaches Siena, for centuries Florence's great rival and today one of the best preserved medieval cities in Europe; its historic centre is also a UNESCO World Heritage Site. All roads in the old town lead down to Piazza del Campo, the famous shell-shaped square that slopes towards the Palazzo Pubblico, the brick town hall built around 1300.

Beside the town hall rises the slender Torre del Mangia, more than one hundred metres tall, which can be climbed for a remarkable view. Twice a year, on 2 July and 16 August, the square hosts the Palio, the historic horse race between the city's districts. Anyone looking for a Siena day trip from Florence will find that this square alone is worth the journey.

Siena Cathedral and the medieval districts

A short climb from the Campo brings you to Siena Cathedral, striped in white and dark green marble, with a richly carved Gothic façade. Inside, the inlaid marble floor, the colourful Piccolomini Library and the pulpit are among the treasures of Tuscan art. Entry tickets are not included, so you can decide during your free time whether to go in; plan about an hour for the visit.

Siena is divided into historic districts called contrade, each with its own name, emblem, fountain and church; look for their coloured flags and plaques on the walls as you wander. The best time to visit Siena is spring or early autumn, when the light is soft and the lanes are pleasant. At the end of the afternoon the coach returns to Florence in about an hour and a half.