Self-guided walking
7 nights,
twin centre
Level: 2+
Moderate plus
Headwater
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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.
You start in the stunning San Gimignano, a lovely hilltop town, with its distinctive skyline (nicknamed Medieval Manhattan!), it is a must for any visitor to Tuscany. It is most famous for its medieval towers, reputed to have come into being because of a dispute amongst affluent neighbours. The surrounding landscape is dominated by vines so there are plenty of wine tasting opportunities here too!
On your journey you join the famous Via Francigena and visit the medieval Colle di Val D'Elsa offering great views across the Elsa Valley. Finally you reach a real Etruscan Gem, Volterra, with its tangle of alleys, home to alabaster workshops and secret chapels. As one of the oldest towns in Italy, Volterra is known for its rich history and well-preserved medieval architecture. Originally an important Etruscan city, it later flourished under Roman rule and retains a wealth of historical sites, including ancient walls, a Roman theatre, and the impressive Palazzo dei Priori. Famous for its alabaster craftsmanship, Volterra offers stunning views of the surrounding countryside and has a unique, timeless atmosphere that has inspired artists and writers for centuries.
Our carefully picked hotels are centrally located within the town walls, each converted from historical buildings while preserving their original charm. Being centrally located you will have the opportunity to enjoy the local cuisine in nearby restaurants. Perhaps try pappardelle alla lepre (fresh ribbons of pasta with a hare sauce) or bruschetta (toasted bread rubbed with garlic and olive oil, topped with sun-ripened tomatoes), all washed down by a glass or two of full-bodied Chianti!
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.
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Hairdryer
WiFi
TV
Aircon
Safe
Tea/coffee
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.
Room upgrades: Double room with view and balcony
Upgrade to a room with a private balcony and immerse yourself in the stunning vistas of San Gimignano.
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.
Take a bus this morning from San Gimignano to Colle di Val D'Elsa (ticket payable locally) and follow in pilgrims' footsteps along the Via Francigena. 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 retracing your steps to rejoin the pilgrim path up to San Gimignano.
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.
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.
You stay at Hotel San Lino.
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MinibarAirconSafe
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 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)
For your final day, walk along picturesque strade bianche, the famous white gravel roads lined by iconic cypress trees through the rolling hills. Wander through the 'Portale' an artwork by an influential Italian sculptor from Volterra; Mauro Staccioli's sculptures are known for their abstract and minimalist style that integrate seamlessly with the town's historic and natural environment. Once you reach the end of your walk pop on a local bus (ticket payable locally) to bring 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.
After breakfast leave Volterra
These tour only prices are based on two people sharing. Single supplement from $278.
Call now to speak to our specialist team at 0044 1606 720199 or email us at sales@headwater.com for enquiries or to book your trip.
Self-guided walking
7 nights,
twin centre
Level: 2+
Moderate plus
Headwater
Navigation App
