Chianti cycling holiday in Tuscany, self guided

“Our only tailor made holiday cycling through the Chianti region of Tuscany, Italy, self guided and staying in exquisite accommodation with bags transferred for you. ”


4 days of cycling in Chianti wine country | Volterra | Gambassi Terme | Pancole | Colle di Val d'Elsa | Pescille | San Gimignano | Era Valley

Description of Chianti cycling holiday in Tuscany, self guided

This eight night Chianti cycling holiday is a perfectly crafted itinerary that allows you to take in this stunning region’s scenery, outstanding hotels, unforgettable cuisine and of course, plenty of cheeky Chianti. This is a tailor made holiday and so we can adapt it according to your interests and needs. However, this route is one of our most popular Tuscany holidays with four days of moderate level cycling but plenty of days in between to enjoy stunning towns and cultural heritage.

Your holiday starts in Volterra, the hilltop beauty where medieval heritage is everywhere you turn including a Romanesque cathedrals and a Roman amphitheatre and other Etruscan exquisite beauties. From here you cycle through tranquil country lanes to the stunning towns and villages of Pancole, Colle and Pescille. Cycling between 30-40km per day, but with intermittent days off so that you can take in the beauty spots where you spend each night, this is a beautifully paced cycling holiday.

Equally beautiful are the hotels where you stay, but then again Chianti does classy very well. You will stay in a mix of three and four star hotels, all with pools to cool down in at the end of ‘another tough day in Tuscany’. They all vary in style too. In Colle di Val d'Elsa, for example, your hotel is a converted 12th century Benedictine abbey, with original frescoes complete, and in Volterra the panoramic view from the infinity pool is one of those ones where you almost have to pinch yourself to make sure it is real. The food and wine are also definitely real, and always exquisite. You certainly will never go hungry on one of our cycling holidays in Tuscany.

Travel Team

If you'd like to chat about this holiday or need help finding one we're very happy to help. The Travel Team.

01273 823 700 Calling from outside the UK?

Departure information

This holiday has departures every two days from May to October, please enquire for availability on all your tailormade trips.
Travelling by train:
We offer the possibility of travelling by train to and from the UK for this trip and can book this for you if required. Please enquire for further details.

Responsible tourism

As the pioneers of responsible tourism, we screen every trip so you can travel knowing your holiday will help support conservation and local people.

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.


Popular similar holidays

Matera to Puglia cycle in Italy

Matera to Puglia cycle in Italy

Nestled between the Adriatic and Ionian seas

From £1599 - £1999 8 days including UK flights

Cycling tours in Italy, Dolomites to Venice

Cycling tours in Italy, Dolomites to Venice

One of Europe's unique mountain landscapes

From £1599 - £1999 8 days including UK flights

Sicily cycling holiday in Italy

Sicily cycling holiday in Italy

Ride through Sicily's UNESCO sites of Siracusa, Noto, Modica and Ragusa

From £1699 - £1999 8 days including UK flights

Umbria to Tuscany cycling & cooking holiday

Umbria to Tuscany cycling & cooking holiday

Cycling and cooking holiday between Umbria and Tuscany

From €1120 - €1160 6 days excluding flights