Pisa to Florence via Chianti Cycle

Make your own way to Pisa, famous for its magical Piazza dei Miracoli (Square of Miracles) with characteristic Leaning Tower. A UNESCO World Heritage site since 1987, Pisa has a large number of monuments as well as the friendly and lively atmosphere of a university city. Bike delivery is in the evening of day 1 (6pm) or morning of day 2. We can assist with booking pre-tour accommodation on request.

The cycle route begins along the river Arno where you soon reach Pontedera, a rather modernized district, home to the wine company Castellani, and a sweets factory called Amedei. Continue through olive groves and vineyards, perfect for an immersion in nature. Finally you will reach the thermal town of Casciana Terme, famous for its Etruscan roots and where thermal water is said to have been discovered by Countess Matilda of Tuscany in the 12th century. Elevation: +290m/951ft, -180m/590ft

Following the Via Francigena pilgrim route, today's cycle leads through vineyards and rolling hills to the medieval hilltop town of San Gimignano. With its UNESCO listed centre, the town is encircled by 13th-century walls and is best known for its skyline of medieval towers. In the evening, treat yourself with the local exquisite cuisine! Elevation: +755m/2477ft, -545m/1788ft Subject to availability, the alternative overnight stay may be in Colle Val d’Elsa (70km/44mi, elevation +1000m/3280ft, -980m/3215ft)

Following the centuries old Via Francigena, you'll have views of Mount Maggio and the castle of Monteriggioni, Dante's subject in his famous literary pieces. The superb medieval town of Siena is ahead; you'll recognise it by the historic brick buildings and the crown of Torre del Mangia. Take time to sit in Piazza del Campo, where the famous Palio horse race takes place each year in July and August. Elevation: +740m/2428ft, -675m/2215ft If your stage starts from Colle Val d’Elsa, today's ride is 25km/15.6mi, elevation +445m/1460ft, -242m/794ft

Today's first stop is Castagnolli, where you can admire Brolio Castle, home to the Ricasoli family and today a well-managed wine cellar. Continue to Radda in Chianti, a classic Chianti village nestled in the verdant hills among remnants of the Etruscan age, and Panzano, a lush green district with a countryside charm. Greve in Chianti is up next, where the famous Chianti Classico Wine Festival is held every year in September. A sip of the local wine will fire up your senses. Elevation: +935m/3068ft, -1045m/3428ft

A shorter cycle day today with free time on arrival to explore one of the world's most beautiful cities. The first leg is to the small town of Mercatale, where there are wine-tasting opportunities at its local wine cellars. After ten kilometres you'll arrive at Impruneta, a neighbouring district filled with terracotta art. Back on your bike, Florence awaits! Known for its wealth of culture, architecture and art, we recommend not missing the Duomo, the Piazza della Signoria, the Uffizi Gallery, the Ponte Vecchio over the Arno River, and Michelangelo's statue of David. Overnight in Florence. Elevation: +660m/2165ft, -840m/2756ft

After breakfast the trip concludes. We can assist with booking extra nights on request.