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Italy: Tuscany

Treasures of Tuscany Walk: San Gimignano to Volterra

Trip code: W07TY

Average customer rating 4.0 / 5(1 verified reviews)

Self-Guided Walking
7 nights twin centre
Moderate
CO₂ rating 1/5
Headwater Navigation app

Trip highlights

Quintessential Italian landscapes: rolling
hills, sunflowers, endless vines and
hilltop hamlets

Scenic walking on Etruscan trails and
pilgrims’ paths; wildlife in abundance

Mouth-watering local cuisine;
world-famous wines

Optional day trip to Siena

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Trip details

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. You’ll feel as though you’re 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.

What's included

Included

  • 7 nights in 3-star and 4-star accommodation
  • All breakfasts
  • Headwater navigation app
  • Luggage transfers between hotels
  • Walk Transfer on day 5

Not included

  • Flights
  • Local taxes/fees
  • Travel insurance

Travel options

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

Itinerary

Route map, with each night's stop marked
The full route, night by night. Select the map to view it full screen.

Day 1 · —Arrive in San Gimignano

Arrive in San Gimignano

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

Hotel Cisterna external
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Hotel La Cisterna

San Gimignano

  • Air conditioning
  • Hairdryers
  • Safe
  • Shops
  • Tea & coffee
  • Television
  • Wifi access

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 caffé.

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.

Day 2 · 15km/9.3mi or 10km/6.2miSan Gimignano Loop Walk

San Gimignano Loop Walk

Leave San Gimignano’s 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 d’Elsa. Along route, you’ll find an olive mill where you can sample some of Tuscany’s 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.

Elevation

San Gimignano Loop Walk elevation profile

Day 3 · 14km/8.7miSan Gimignano to Colle Di Val D'Elsa walk

San Gimignano to Colle Di Val D'Elsa walk

From San Gimignano follow in the pilgrim’s footsteps along the Via Francigena to Colle di Val D’Elsa. Internationally renowned for its crystal production Colle di Val d’Elsa 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 D’Elsa. Once you have finished exploring Colle di Val D’Elsa pop on a bus back to San Gimignano (ticket payable locally).

Elevation

San Gimignano to Colle Di Val D'Elsa walk elevation profile

Day 4 · —San Gimignano Free Day

San Gimignano Free Day

Visit San Gimignano’s 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.

Day 5 · 22km/13.7miSan Gimignano to Volterra walk

San Gimignano to Volterra walk

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 Volterra’s medieval gates, where you have time to relax in the pool.

Elevation

San Gimignano to Volterra walk elevation profile

You stay at Hotel San Lino

Hotel San Lino
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Hotel San Lino

Volterra

  • Air conditioning
  • American Express
  • Hairdryers
  • Mastercard
  • Minibar
  • Safe
  • Swimming pool
  • Television
  • Wifi access

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.

Day 6 · 18km/11.2mi or 10km/6.2miVolterra Salt Mine walk

Volterra Salt Mine walk

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 Volterra’s wealth. The salt trade allowed Volterra to become a powerful economic centre and funded the construction of many of its impressive buildings. Today, Volterra’s 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)

Elevation

Volterra Salt Mine walk elevation profile

Day 7 · 11km/6.8miVolterra Loop Walk

Volterra Loop Walk

This walk explores the edges of Volterra, where the town’s Etruscan origins, medieval engineering and striking geology come together. Leaving the historic centre, the route reaches Fonte San Felice, one of Volterra’s 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 Volterra’s 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.

Elevation

Volterra Loop Walk elevation profile

Day 8 · —Leave Volterra

Leave Volterra

After breakfast leave Volterra

Extending your holiday

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.

What our travellers say

Very nice areas and reasonably priced

Mr Pettet
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Positive impact

Carbon score for this trip

13.0

Kg CO₂e

per person, per night

Relative to other Headwater trips

We measure emissions from the parts of the holiday we organise — including accommodation, in-trip transport, meals and activities — and express them as CO₂e per person, per night. Our label doesn’t 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

From£849per person