Experience the timeless countryside cycling of central Italy as you cycle through the stunning Italian landscapes. Your journey starts in Volterra where you'll cycle through the magnificent Tuscan countryside and onto Colle di Val d'Elsa where you will explore the great art cities of Florence and Siena while getting to taste the great food and wine that Chianti is well renowned for.

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Why We Love It

Enjoy scenically stunning cycling through the quintessential Italian landscapes of central Italy from rolling hills to fields bright with sunflowers.

Discover the wonderful art and architecture of Florence and Siena such as Etruscan, Roman, Renaissance and Mediaeval.

Experience the great food and wine that Chianti is well known for when you indulge in the evening meals that celebrate the local flavours.

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Day by day Itinerary

Classic Chianti Cycling

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Day 1


We meet you at Pisa airport and take you (75mins) to Volterra where you've time for a dip in the pool and a wander round its tangle of cobbled alleys and hidden squares before dinner.

Day 2

Volterra - Certaldo

A welcome introductory downhill whizz out of hilltop Volterra and down into the pretty Era Valley where spectacular views of the surrounding timeless Tuscan countryside open up as you pedal! After climbing out of the valley, you'll soon pass through the pretty hamlet of Castagno where we suggest a coffee stop in the local bar. Your route continues on to Gambassi Terme, a well preserved spa town with cobbled streets, C12 church and lovely shaded gardens. It's a gentle downhill cycle to your luxury 4-star hotel in postcard-pretty Certaldo where secluded gardens and welcome swimming pool await!

Day 3


Beautifully preserved, yet largely undiscovered, Certaldo is arguably the jewel in the Middle Aged crown of Tuscany. Split into two distinct halves, the ancient vermillion-hued buildings of Certaldo Alto (also known as Castello) create a spectacle more dramatic than any film set and offer spectacular balcony views across the surrounding countryside. The lower half of the town, Certaldo Basso, is more modern with a plethora of shops, bars and restaurants, and the two are linked by a popular funicular.

Day 4

Certaldo - Colle di Val d'Elsa

Wine lovers are in for a real treat today as you'll mainly be following the official, mostly off-road, Chianti Wine Route. There are lots of tasting opportunities here and, don't forget, we can collect any purchases for you. It's then downhill into Poggibonsi where the old town makes for the perfect lunch stop. As you leave the town, admire the fabulous views before your final poppy-lined stretch past sunflower fields brings you to the hilltop town of Colle di Val d'Elsa. Here, the fabulous 4-star Relais della Rovere hotel, a beautifully converted C14 Benedictine Abbey with lovely pool and gardens, is home for the next four nights.

Day 5

Colle di Val d'Elsa

There is so much to see and do in and around Colle di Val d'Elsa that you really will be spoiled for choice. However today we recommend hopping on the local bus (from just outside the hotel) for the 30min ride to the great mediaeval city of Siena. Visit the Palazzo Pubblico with its impressive pre-Renaissance frescoes and climb the Torre del Mangia for the best views of the town and surrounding Sienese countryside. For lunch, or simply for a people-watching drink, there is no better place than Siena's beautiful shell-shaped Piazza del Campo.

Day 6

Colle di Val d'Elsa

After a fairly long day yesterday, we propose that you spend a relaxed morning in Colle di Val d'Elsa. The historic town dates back to Etruscan times with Cathedral, museums and fine Renaissance buildings. After lunch in the old square, maybe some time by the pool before a pre-dinner stroll along the lovely river Elsa where limestone-rich rapids come crashing dramatically downstream.

Day 7

Colle di Val d'Elsa

No trip to Tuscany would be complete without a visit to the charming city of Florence, arguably the most beautiful city in the world! It's just an hour on the local bus (which leaves from just outside the hotel) giving you plenty of time to explore the Uffizi (closed Mon), Duomo and Baptistery. If you want to escape the crowds, we suggest you cross the Ponte Vecchio to the quieter side of the Arno to visit the Boboli Gardens.

Day 8

Colle di Val d'Elsa - Pescille

Back on the bike this morning with superb rolling views before the ride up to Casole d'Elsa, a beautiful village characterised by ancient vermilion-hued buildings and blessed with stunning balcony views from its hilltop position. Take time to explore its C12 church (frescoes by Gano da Siena) and impressive fortress before an early lunch perhaps in the lovely piazza. You then wind north through wonderfully scenic countryside, the fabulous mediaeval towers of San Gimignano providing a formidable backdrop as you pedal on to Pescille.

Day 9


San Gimignano is just a short cycle away, its stunning mediaeval towers giving this hilltop town a distinctive Manhattan-style skyline. Explore its myriad of narrow streets and many hidden cobbled squares before returning to your tranquil hotel for a refreshing dip in the sparkling swimming pool.

Day 10

Pescille - Volterra

It's a short downhill ride to San Gimignano before a gentle climb up through classic Tuscan landscapes of vines, olive groves and fields ablaze with sunflowers before the almost entirely downhill cycle into the pretty Era Valley. There's a real sense of achievement on your final pedal through open countryside, enjoying spectacular views, before your final climb back to the ancient cobbled streets of Volterra.

Day 11


We take you to Pisa airport after breakfast to connect with your flight home.

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