Chianti Classico Road Cycling Tour: The Ultimate Tuscan Challenge

Experience the pure essence of Italian road cycling – home of the Giro d’Italia and Eroica – through the legendary landscapes of Chianti Classico, where world-class terrain meets breathtaking beauty on roads that have challenged and inspired cyclists for generations.

This one day Tuscany road cycling tour is crafted exclusively for serious road cyclists who seek authentic challenges amidst some of the world’s most spectacular scenery and want to ride exceptional roads through Italy’s most celebrated wine region.

Price – €190 per person*

*minimum of two participants required

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Tour Details

• Distance: 40 kilometers (25 miles) standard tour. Longer on request
• Duration: Full day
• Difficulty: Advanced – expect 700m/2300 feet of elevation gain over the 40km
• Group Size: Small groups of 2-8 for personalized attention
• Transportation: Return transfer from Florence included. A pickup at your hotel/villa in another location can be arranged by request.
• At The End Of The Ride: Tuscan light lunch with Chianti Classico wine tasting

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Legendary Cycling Territory

Chianti Classico represents the pinnacle of Tuscan road cycling, featuring perfectly maintained tarmac that winds through rolling hills, challenging climbs, and exhilarating descents. These are the roads where local cycling legends like Gino Bartalli have trained. Every turn reveals another postcard-worthy vista.

Our regular loop cover 40km kilometers of carefully selected roads that showcase the region’s diverse terrain. From gentle rolling sections through vineyard valleys to sustained climbs that test your fitness, each kilometer offers something different. The high-quality riding surface that makes Chianti famous among cycling enthusiasts worldwide.

Classic Chianti Villages

Your journey takes you through some of Tuscany’s most picturesque hill towns. We drive from Florence out to Castellina in Chianti, a classic hill top Tuscan town which offers panoramic views where our ride begins. On the way round we will discover small villages stopping for a water refill/coffee stop in Radda In Chianti before completing the ride.

Professional-Grade Experience

Your expert guide brings years of local cycling knowledge, having ridden on these roads extensively. If you would like to ride more than the standard 40km loop, let us know. Whether you’re training for an event, exploring new territory, or simply want to experience world-class cycling, we can ensure the perfect balance of challenge and enjoyment.

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What’s Included

• High-performance carbon road bike
• Expert English-speaking guide
• Professional helmet and safety equipment
• Scenic photo stops and cultural commentary
• Tuscan Light Lunch and Chianti wine tasting (for the standard ride)
• Comfortable return transportation to starting point
• Van support available for private groups

Like the idea of a physical challenge but also fancy a trip to Siena after? Have a look at our Florence to Siena Tour – the standard version

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