Tuscany on Foot

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Tuscany on Foot

Trip Highlights

  • Classic Tuscan walking
  • Picturesque landscapes and villages
  • Enjoy famous local Wines like ‘Vernacchi’

Trip Summary

This walk threads together some of the most attractive towns and villages in Tuscany in an eloquent procession. It is a perfect introduction to the region and for people who love museums and galleries, Gothic and Romanesque architecture, there is plenty to see and do. You have plenty of time for attraction visits on most days. However the emphasis of the tour is to enjoy the countryside, the rolling vineyards, the poppies in spring and the wild cyclamen in autumn. Most of all, many of the views have changed little for hundreds of years. This is a relatively gentle tour that is suitable for those who are new to walking tours. More experienced walkers will also enjoy the classic Tuscan landscape of small but sometimes steep hills, olive groves and vineyards. We pass close to the classic wine-growing region of the Vernacchi and Chianti and visit the historic towns of Volterra, San Gimignano (with its famous towers), Colle Val d’Elsa and Siena. There is also an opportunity to visit Pisa with its famous attractions and if you decide to extend the tour by a day or two you can visit the celebrated city of Florence. The walking takes in classic Tuscan landscapes and as most days are not too long, you will have plenty of time to sightsee, or picnic.


Easy to Moderate. There are nonetheless some steep and quite long hills, some fairly steep but short descents and some paths with rough gravel, stony and occasionally muddy surfaces. Fitness: High standard of fitness is not necessary but clients should be able to walk for up to 7 hours a day in hot sun on dusty or stony tracks.


Make your own way to Pontedera, where you change onto a local bus service (except Sundays) to Volterra. If you are arriving early or having and extra day we include a walking option to see the town in detail and visit the Balze Cliffs. For Sunday arrivals we recommend the local transfer service. Accommodation: Our first choice is in a welcoming and comfortable 3 star hotel, which is in fact a restored villa from the late 17th century. It is situated in a peaceful area near the medieval town wall. The hotel has a magnificent panoramic view of the area. All rooms are ensuite and the hotel also boasts an outdoor swimming pool.

Meals:  D

Walk out of Volterra, descending by the huge Medici Fortress. The way soon leaves the busy roads and you are walking past an old convent before taking a quiet lane and then a footpath through fields, dropping down into the valley of the Era Morta. Here you join a gravel farm track that ascends steeply to join a rolling ridge, passing farms and with vast vistas over the surrounding landscape filled with mixed arable, vineyards, the odd flock of sheep not to mention a few lines of Cypress trees. Eventually you arrive at a beautiful agriturismo built from a medieval tower house. Accommodation: Agriturismo at around 600 metres altitude. it has 5 double rooms and 3 comfortable apartments furnished in rustic style created in a twelfth-century tower-house, from which you can admire beautiful landscapes. In the restaurant you can taste the traditional flavors of Tuscan cuisine, tasty game dishes, and many other specialties. If you arrive early take advantage of the swimming pool. Note: In busy periods we might need to organise transfers back to Volterra for a second night as room numbers are limited

Meals:  B,D

From Sensano the lane continues to join a quiet rural road which undulates a couple of kms to turn off easterly through some interesting forest including several species of oak and strawberry trees, passing a farm complex and open fields before re-entering the forest with wild cyclamen in flower in autumn. Passing the medieval ruins of Castelvecchio, you continue to the pretty village of San Donato and the small hamlet of Montauto with fine views of San Gimignano. Then continuing by farm track and/or road to San Gimignano, known as the town of the beautiful towers that has dominated the hills south of the Elsa Valley since Etruscan times. There is much to explore in this small town in particular the narrow streets and squares of the medieval quarter. Accommodation:Our first choice is a 3-star hotel set in the pulsating heart of the town of towers, little changed for 600 years.

Meals:  B

You follow a white road along a broad panoramic ridge with fine views back to the towers of San Gimignano. On either side are vineyards (source of the local dry white Vernaccia), olive groves and cypress avenues. Later climb up through shady woods to the small village of Montecchio and across fields to Borgatello, and on into Colle Val d’Elsa. The walk can be extended to visit the old church of Badia a Coneo on the 'Via Francigena' for a picnic, although this is normally closed. The fascinating old town of Colle Alto occupies the crest of a ridge high above the valley of the Elsa. Accommodation: Our B&B is in the centre of Colle val d’Elsa. It has 10 beautifully decorated ensuite rooms.

Meals:  B

After walking out of Colle through the suburbs and then through attractive undulating woodland following at one point a beautiful clear stream, you cross a broad and mostly treeless agricultural plain, with farming hamlets such as Scarna and Acquaviva. As you approach the base of the densely wooded Montagnola Hills you reach the attractive village of Strove, with the nearby manor house of Castel Petraia. At the village of Abbadia a Isola you should stop to see the abbey church. You arrive at the base of the little hill, clad with vineyards, on which is built the medieval walled village of Monteriggioni with its famous watchtowers. Accommodation: We spend the night in the 4* Hotel Monteriggioni. It is centrally located within this walled town and it has kept many of its original features.

Meals:  B

Today you have the choice of a long walk directly into Siena on the 'Via Francigena' Pilgrims route, or a shorter walk via the hamlet of Il Ceppo, where there is a great restaurant for lunch (closed on Tuesdays). From here take a taxi or infrequent bus into Siena (not included in the tour price). After settling in to the hotel you will find all the famous places of this city within walking distance, with the Palazza IL Campo being the centre of this medieval city. There are many museums, churches, and the huge Pisan Romanesque and Gothic cathedral. You can easily get lost in the warren of streets, all arranged into areas called 'Contrada’, as they have done for hundreds of years and where the Sienese population gain their group loyalties and rivalries. Accommodation: In the lively and sophisticated city of Siena we stay at a small, comfortable 3 star town hotel, all rooms ensuite.

Meals:  B

Depart Siena after breakfast.

Meals:  B

What's Included

  • 6 breakfasts, 2 dinners
  • 2 nights accommodation in 3 star hotels, 1 night in a 4 star hotel, 1 agriturismo and 1 B&B on a twin share basis with ensuite facilities
  • Luggage transfer (1 bag per person not weighing anymore than 20kg)
  • Information pack including route notes & maps
  • Emergency hotline

What's Not Included

  • 4 evening meals, all lunches & beverages
  • Entrance fees
  • Travel insurance
  • Travel to the start and from the end point of the trip
  • Personal expenses such as laundry and phone calls

Upcoming Travel Dates


Beautiful place to walk at the end of May 2019 - wild flowers everywhere and even saw to wild boar families prancing along the edge of a field. Trip preparations, sherpa service, and extra contextual notes were fabulous.

P. Anderson, CA, USA, 06 Jun 2019

We had a lovely time and thoroughly enjoyed the whole walk. The tour was correctly graded and classify for beginners. The hours/distances covered each day were roughly as expected. Route notes and maps good. At times the distances were over or understated and giving times to cover distance has problems with different walking paces.

B. & R. Kelly, NSW, Australia, 19 Jun 2017


Duration:7 Days
Starting Point:Volterra
Finishing Point:Siena
Activities:Self-Guided Walking
Grade:introductory to moderate  Click for more information
Trip Code:JT7
Prices From:GBP£1080 Per Person
Please do not book any flights or extra arrangements until such time that your booking is confirmed by Sherpa Expeditions by phone or email.