Tuscany cycling tour

We will collect you from Florence Airport during the morning and transfer you to Chianti in the heart of Tuscany. After the official tour welcome the bikes will be set-up and a picturesque warm-up ride through the vineyards awaits. Tonight you will enjoy dinner with the tour guides.

Distance: 50km / Meals: Dinner Included / Sleep: Chianti

Today will be the perfect time to start familiarising yourself with the local landscapes and the riding on offer. The Chianti region is loved for its natural beauty, postcard perfect towns, friendly locals, quality wine and fresh produce!

The riding is brilliant as you pedal along winding roads past old agricultural estates and manor houses. The roads surrounding the Castello di Brolio region are first class and cycling through the gardens of this rural palace is always a highlight. The Ricasoli family are the original owners of this Tuscan jewel and the extensive vineyards on-ground are actually Italy’s oldest winery. Amazingly, this family has been fine-tuning their craft since way back in 1141!

Distance: 75km / Meals: Breakfast Included / Sleep: Chianti

Today you will ride a combined asphalt and white gravel road route straight from  l´Eroica Gran Fondo. L’Eroica was born from a pure passion for cycling with the aim of rediscovering the authentic roots of a truly beautiful sport. But we didn’t need to convince you about that! As you pedal along you can imagine the heroic days of Binda, Gagliardoni and Bartali as quaint towns with names like Greve, Panzano and Radda in Chianti roll-on by.

We will have a post-ride celebration drink back at the hotel to mark your cycling achievements.

Distance: 80km / Meals: Breakfast & Dinner Included / Sleep: Chianti

Today we change base and move higher up into the Chianti region. The hotel to hotel ride will see you finish the ride up at the small mountain hamlet of Volpaia. The beautiful views and wine tradition will have you captivated. We will also be pleased to organise an official wine tasting beneath the castle in the town centre!

Later in the evening dinner will be served in one of our favourite local and very homely osterias.

Distance: 75km / Meals: Breakfast & Dinner Included / Sleep: Volpaia

This morning the ride heads west towards Castellini in Chianti. Along the way though we first take a coffee stop in San Donato which is one of the most charming hilltop villages in Chianti. You will ride past the remains of its medieval walls and old gates that have seen the test of time!

Today there are a few climbs ranging between 1.5 – 6km (3-4% average grade). Lunch will be called in ‘Castellina’. This is a town rich in Estruscan history with evidence dating back to the 7th Century BC. After lunch we will be sure to ride past the Etruscan burial mound on the outskirts of town. All that remains now is the final test back up to our accommodation in Volpaia. The 3.5km climb at 7% average grade will be worthy of yet another cold beer or glass of Chianti red!!  

Distance: 65km / Meals: Breakfast Included / Sleep: Volpaia

After breakfast we say goodbye to Chianti and cycle for Siena. The cycling follows rolling terrain with several ‘white gravel’ road detours. The arrival to Piazza del Campo in Siena is a truly special moment. The medieval piazza is one of Europe’s greatest squares! The twice-a-year horse-race, Palio di Siena, is held around the edges of the piazza.

During the late afternoon there will be plenty of time to explore the medieval old town. The streets resemble an open-air museum and finishing for a group dinner in this magical city will be something to remember for years to come.

Distance: 75km / Meals: Breakfast & Dinner Included / Sleep: Siena

Today´s route heads towards Asciano and the famous ´Senesi Crete´. The clay fields during earlier days were overworked and abandoned and erosive forces have created a lunar landscape. As the kilometres roll-by the beautiful rural landscapes of the Val d´Orcia are uncovered (UNESCO World Heritage Site). Follow roads lined with the regions characteristic and emblematic cypress trees. The jewel of the Val d´Orcia region is the small renaissance towns and there will be time to soak up the medieval history of Pienza and Montalcino. Post-ride there will be a 1hr drive back to Siena.

Distance: 75km / Meals: Breakfast Included / Sleep: Siena

The small medieval walled town of San Gimignano is a must-see when visiting Tuscany. Its 13 medieval towers reach for the heavens and were built as symbols of family status. The countryside between Siena and San Gimignano is highly regarded for its historical, cultural and natural treasures. The undulating roads will keep you interested throughout as the ride moves north-west from Siena. There are several 1-3km climbs and descents on twisting roads that pass quiet towns. The ride will finish in San Gimignano where we will ‘raise a toast’ before giving you the chance to explore this beautiful town. All that remains now is a short drive into Florence and a farewell dinner to recap what has been an amazing week on and off the bikes!

Distance: 80km / Meals: Breakfast & Dinner Included / Sleep: Florence

Following breakfast our guides will be available to transfer you to Florence Airport. We look forward to cycling with you again soon!

Meals: Breakfast included