









Italy: Tuscany
Average customer rating 4.0 / 5(1 verified reviews)
On this self-guided, 7 night walking holiday, you explore the timeless countryside around two of the most scenic hilltop towns of Tuscany, San Gimignano and Volterra. Youโll feel as though youโre strolling through history as you discover sleepy hilltop hamlets, crowning sun-dappled hills, verdant vineyards and panoramic picnic spots in fields ablaze with sunflowers. You also have the option to visit the eternal city of Siena.
Our travel specialists can arrange flights, rail and transfers to this holiday from wherever you are. Call us to plan your journey. +44 1606 720099


Arrive at your accommodation in the main square of San Gimignano with great views of the famous Tuscan hills.
You stay at Hotel La Cisterna

San Gimignano
Enjoy your stay at this picturesque 14th century building hotel nestled in the heart of San Gimignano. With your room either overlooking the main piazza or the classic Tuscan countryside be prepared to lose time as you soak in the timeless charm of San Gimignano.
La Cisterna offers beautifully decorated rooms in both Florentine and modern style all of which are equipped with air conditioning, free Wifi and a flat-screen satellite TV.
A continental buffet breakfast is served at the on site restaurant Le Terrazze, where you can enjoy panoramic views over the historical square whilst your sip on your morning caffรฉ.
The advantageous position of this property will allow you to easily reach shops, points of interest and a vast choice of restaurants in the town centre.

Leave San Gimignanoโs ancient town walls behind you as you wind your way past verdant olive groves, lush vineyards and majestic cypress trees into the heart of spectacular Val dโElsa. Along route, youโll find an olive mill where you can sample some of Tuscanyโs finest olive oil and learn about the production of this exceptional local delicacy. Finally admire the views of San Gimignano as you loop through rolling countryside along tranquil gravel roads back to San Gimignano to enjoy some Chianti wine and traditional Tuscan crostini.
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From San Gimignano follow in the pilgrimโs footsteps along the Via Francigena to Colle di Val DโElsa. Internationally renowned for its crystal production Colle di Val dโElsa is a charming town filled with medieval architecture with evidence of human settlements dating back to the Etruscans.
Bright with sunflowers and fragrant apple orchards, the historic Via Francigena passes tiny hamlets and lonely chapels towards the lazy Foci River. You may like to make a short detour to take in a wine tasting at Montauto, before rejoining the pilgrim path to Colle di Val DโElsa. Once you have finished exploring Colle di Val DโElsa pop on a bus back to San Gimignano (ticket payable locally).
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Visit San Gimignanoโs mystical towers built by warring neighbours in the 12th century to outdo one another! Or for a longer day out, hop on a local bus to Siena (1 hour), a perfectly preserved medieval gem with a stunning striped 14th century Gothic cathedral and beautiful square.

A short taxi ride (10 minutes) from your hotel takes you to the start of the walk in Caggio, at the Castelvecchio Nature Reserve. From here you follow a woodland trail dotted with rock roses and wild strawberry plants to reach a panoramic strada bianca, where hawks soar overhead. With open views across cypress-studded ochre fields, you pass through the historic hamlets of Sensano and Ulignano, before ascending an ancient mule track to Volterra.
Arrive at your 4 star hotel just within Volterraโs medieval gates, where you have time to relax in the pool.
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You stay at Hotel San Lino

Volterra
Hotel San Lino is set within the medieval walls of Volterra, a 5-minute walk from Piazza dei Priori. Originally built as a convent in 1480, Hotel San Lino has been attentively renovated to preserve the original architectural features that celebrate its historical charm.
Rooms here are spacious and bright, exquisitely decorated in Tuscan style, with traditional terracotta floors and wooden furniture. All rooms are equipped with ensuite bathroom, TV, air conditioning and Wifi. You will stay in a superior room with a view of the swimming pool.
A buffet breakfast is served in the main dining room, and includes homemade cakes, cured meats, yogurt and cereals.
The property also benefits from a garden with outdoor swimming pool and panoramic terrace.

Today you follow the old rack railway that used to connect Volterra to the salt mines; with far reaching vistas of endless rolling hills and verdant landscape, this is quintessential Tuscany at its best. This is not only a serene walking experience but also a glimpse into the rich cultural heritage of the area, where the salt mines played a pivotal role in local history by contributing significantly to Volterraโs wealth. The salt trade allowed Volterra to become a powerful economic centre and funded the construction of many of its impressive buildings. Today, Volterraโs salt is still renowned and is used throughout Italy by chefs who appreciate high-quality ingredients.
Option to reduce the walking distance by returning to Volterra by bus. (ticket payable locally)
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This walk explores the edges of Volterra, where the townโs Etruscan origins, medieval engineering and striking geology come together. Leaving the historic centre, the route reaches Fonte San Felice, one of Volterraโs most important medieval water structures, built in 1319. Follow paths that lead towards the Necropolis of Colombaie, an archaeological area that has produced some of Volterraโs most important recent discoveries. The end of your walk brings you back into the centre of Volterra for a well earned gelato.
Alternatively, you might choose to relax by the pool or delve into the fascinating local attractions of Volterra. Visit the well-preserved Roman theatre, the Etruscan museum or Palazzo dei priori, one of the oldest town halls in Tuscany.
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After breakfast leave Volterra
If you'd like to extend your trip with extra hotel nights we recommend: Hotel Cosimo De Medici, Florence; Hotel La Luna, Lucca; Hotel Alessandro della Spina, Pisa; Hotel Chiusarelli, Siena.
13.0
Kg COโe
per person, per night
Relative to other Headwater trips
We measure emissions from the parts of the holiday we organise โ including accommodation, in-trip transport, meals and activities โ and express them as COโe per person, per night. Our label doesnโt include your travel to and from the start of the trip. As a Certified B Corp, Headwater is committed to reducing this figure and to positively impacting local communities, the local environment and our staff. Learn more