Chianti cycling holiday in Tuscany, self guided

Hello. If you'd like to chat about this holiday or need help finding one we're very happy to help. Rosy & team.

01273 823 700

Departure information

Our dates are flexible; please enquire for availability

Responsible tourism

Responsible tourism: Chianti cycling holiday in Tuscany, self guided

UK Office

We are well aware of the impact tourism has at home and abroad, and we make every effort to balance the environmental impact of travelling with the immense benefits sustainable tourism can bring to destinations and the people who live there.

So we start in the office: we turn off all electrical equipment every night; we use energy-efficient bulbs; we measure print and paper consumption, and re-cycle wherever possible; we print our brochures on paper from sustainable sources, and send them out in bio-degradable packaging.

Leaders & local suppliers

Chianti: Secrets of San Gimignano

Chianti wines are known throughout the world and all big towns have tasting houses in their historical centres. We suggest however that you instead visit the many farms and aziendeagricole dotted throughout your cycling route where you can stop off, taste and, if you choose buy, wines direct from the wine-makers. Just look out for the venditadiretta signs! And, don’t forget, if you want the Headwater rep to collect any purchases for you, then you just need to give them a call and we’ll pick up for you – no charge, just something we like to offer!

Group size

All our cycling holidays are independent, or self-guided, meaning that no minimum numbers are required to ensure that a trip operates. Mostly, trips depart every two days throughout the season, meaning customers are not restricted to busy weekend travel or costly high season dates. It also allows us to offer total flexibility over travel options and holiday durations.


Cycling has minimal impact on the environment as you provide most of the energy yourself and, when you’re pedalling from village to village, you can enjoy a relationship with locals in a way motorists passing through never can. On a bike, you get off the beaten track and people treat you as a visitor rather than a tourist. Also, by cycling independently, and not having to worry about keeping up with a group, you set the pace so you can soak up the sights, sounds and scents of your surrounds and really get under the skin of the place you’re visiting.

We proactively encourages cycling clients to think about travelling responsibly too: packing light, saving water, buying locally and re-cycling all maps and route notes at the end of their trip. We even re-cycle our old bikes! As part of our on-going maintenance, we often need to replace cycle parts which, although still serviceable, don’t meet our standards for reliability and comfort. So we donate these parts to Colchester-based charity, Re-cycle, who go on to send them to parts of Africa where locals are taught how to ride and look after a bike. This service has proven invaluable over the years for doctors, midwives, etc who sometimes need to quickly get to remote villages.

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