Volterra to San Gimignano walking holiday in Italy

“A self-guided 9 day walking holiday, staying in 4* hotels, with superb food, luggage transferred for you and off the beaten track itineraries.”


Volterra | Berignone Nature Reserve | Casole d'Elsa | Colle di Val d'Elsa | Sienna | Florence | Via Francigena | San Gimignano | Castelvecchio Nature Reserve

Description of Volterra to San Gimignano walking holiday in Italy

This Volterra to San Gimignano walking holiday is a nine day journey through Tuscan rural idylls. It will feel like almost timeless terrain walking through tranquil hilltop hamlets, basking in Tuscan sun which nourishes the vineyards and olive groves that you amble past along the way from hotel to hotel.

The hotels we have selected for you are four star, and the landscapes are always five star. Have your bags transferred for you as you take time to enjoy cultural highlights such as the Etruscan village of Casole d'Elsa or the mystical towers of San Gimignano's. With options to visit Sienna and Florence on ‘days off’. Natural heritage highlights include walks through Berignone Nature Reserve and Castelvecchio Nature Reserve, both stunning. In fact, Tuscany only does stunning really.

All of the hotels have swimming pools, meaning that you can really chill out after a day of walking, as this itinerary includes walks every other day of between 14-22km. So you have plenty of relaxing time too, with no shortage of ways to enjoy Tuscany. Sipping the local Chianti and relishing Tuscan gastronomic specialties.

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.

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Departure information

This holiday has departures every two days from May to October, please enquire for availability on all your tailormade trips.
Our top tip:
Bring walking poles and a sun hat. A lot of exposed hillsides on this trip.
Trip type:
Self-guided walking holiday.
Activity level:
Moderate. 4-6 hours walking/day.
Small 3 and 4 * quality hotels, several with pools.
Flights if booked, accomm., transfers, luggage transfers.
Breakfasts and 6 dinners included. Tuscany trattoria treats abound for lunch.
Solo travellers welcome. Surcharge for own room.

Responsible tourism

Volterra to San Gimignano walking holiday in Italy

Carbon reduction

Your holiday will help support local people and conservation. We must also reduce CO2. Learn about the CO2 emissions of this holiday and how to reduce them.


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 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 local farms and aziende agricole dotted throughout your walking route where you can stop off, taste and, if you choose buy, wines direct from the wine-makers. Just look out for the vendita diretta signs! And, don’t forget, if you want the 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!

Our staff will also suggest places to see and visit locally. Many of our overseas staff have worked for us for many years now – in fact, the 20 returning staff this summer have, between them, clocked up an impressive 189 years!

Group size:
Having no minimum number means that groups sizes can be small and therefore the trips have less impact on the environment.

Walking has minimal impact on the environment as you provide most of the energy yourself and, when you’re strolling from village to village, you can enjoy a relationship with locals in a way motorists passing through never can. On foot, you get off the beaten track, and you’ll find that people treat you as a visitor rather than a tourist. Also, by walking 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 encourage walking 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.

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