Cycling Holiday in Tuscany: Pisa, Chianti, Siena and Florence

Your Tuscan cycling holiday begins in Pisa, home to the world-famous Leaning Tower of Pisa on Piazza dei Miracoli, a UNESCO World Heritage Site. This iconic square also features the impressive cathedral and baptistery, making it the perfect place to start your journey.

Beyond its famous landmarks, Pisa is a lively university city with charming squares, cafés, and traditional trattorias where you can experience authentic Italian atmosphere. End your first day with a relaxing walk along the Arno and enjoy the perfect beginning of your cycling holiday in Tuscany.

Today you cycle through the heart of the Tuscan countryside, passing vineyards, olive groves, and winding cypress-lined roads. Along the way, you pass Pontedera, known for the historic Piaggio Vespa factory and local wine estates.

Your day ends in Casciana Terme, a charming thermal spa town where natural hot springs have been enjoyed since Roman times. Relax in the thermal baths or enjoy a glass of local wine — the perfect ending to your first cycling day in Tuscany.

Today you follow the historic Via Francigena, the ancient pilgrimage route through Tuscany, surrounded by rolling hills, vineyards, and olive groves.

In the afternoon you arrive in San Gimignano, the famous UNESCO World Heritage town known for its medieval towers. Stroll across Piazza della Cisterna, taste a glass of Vernaccia wine, and enjoy panoramic views over the Tuscan countryside.

If you stay in Colle di Val d’Elsa, you will discover a charming town famous for its glassmaking tradition and picturesque streets filled with artisan shops.

Today you continue cycling through the heart of Tuscany towards beautiful Siena. Along the way, you pass Monteriggioni, a perfectly preserved medieval fortified village once described by Dante Alighieri.

Your destination is Siena, one of Italy’s most remarkable historic cities. Piazza del Campo, home to the famous Palio di Siena, forms the lively heart of the city. Visit the impressive gothic cathedral and enjoy an espresso on a sunny terrace.

Today is all about Tuscan wine, castles, and panoramic landscapes. You cycle through the world-famous Chianti region, known for vineyards, medieval villages, and elegant country estates.

Along the route, stop at Castello di Brolio, where the famous Chianti Classico wine is produced. Continue through Radda in Chianti and Panzano in Chianti, two charming villages with lively squares and inviting wine shops.

You finish in Greve in Chianti, considered the heart of the Chianti region. At Piazza Matteotti you can taste local wines or simply enjoy the view over the rolling hills.

Your final cycling day takes you through picturesque villages and vineyards towards Florence. Along the way, you pass Mercatale in Val di Pesa and Impruneta, both known for terracotta craftsmanship and local wine cellars.

As you approach the city, the impressive Florence Cathedral appears on the horizon — a fitting finale to your journey. Walk across Ponte Vecchio, admire the Duomo, and enjoy a well-deserved gelato on a sunny terrace.

After breakfast, your cycling holiday comes to an end. Feel free to stay an extra day in Florence to enjoy its art, culture, and gastronomy. Visit the Uffizi Gallery, admire David by Michelangelo, or stroll through the lively San Lorenzo Market.

A relaxed ending to an unforgettable journey through the heart of Tuscany.