Tuscany on Foot - 11 Days

Tuscany on Foot - 11 Days information and booking

  • Duration
    11 days
  • Group size
  • Difficulty
    introductory - moderate
Check prices & availability

Schedule Details

  • 10 nights hotel/guesthouse/agriturismo


  • Classic Tuscan Walking
  • Picturesque ‘Like Stepping into a Medieval Painting’
  • Quaff Famous Local Wines like ‘Vernacchi’
  • Interesting Locations and Accommodations

Tour description provided by World Expeditions

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, which is suitable for those who are new to walking tours. More experienced walkers will also enjoy the classic Tuscany landscape of small (although sometimes steep) hills, olive groves and vineyards. We pass close to the classic wine-growing region of Chianti, and visit the historic towns of Volterra, San Gimignano (with its famous towers) and Siena. From Siena, we are transferred to the Chianti region and to Radda and Gaiole passing fortified villages and castles. The walking continues onto Panzano before we finally take a local bus onto Greve-in-Chianti for a night and then onto Florence where you have a free day before returning to Pisa for your flight home. Depending on flight times you may have enough time to visit Pisa’s famous attractions (the field of Miracles Leaning Tower and Duomo). The walking takes in classic Tuscan landscapes and as most days are not too long, you will have plenty of time to sight-see, or picnic.

What's included

  • 10 breakfasts, 2 dinners
  • 10 nights accommodation in 2 & 3* hotels a guesthouse and agriturismo on a twin share basis with ensuite facilities
  • Vehicle transfers on day 7 *luggage transfer (except to florence)
  • Information pack including route notes & maps
  • Emergency hotline


Day 1 Arrive Volterra
Either bus or train is taken from Pisa to Pontedera, where you change onto a local bus service (not Sundays) to Volterra. Journey from the airport to the first hotel is not included in the tour price. The combined train and bus fare is around 8 Euros per person. It is possible to reach Volterra by public transport on Sundays, but by a more circuitous and expensive route. If you are arriving early or having an extra day, we include a walk option to see the town in detail and visit the Balze cliffs. Accommodation: Volterra - one of the oldest cities in Italy, in a welcoming and comfortable 3 star hotel which is in fact a villa from the late 17th century that has been restored. It is situated in a peaceful area near the medieval town-wall. The hotel commands a magnificent panoramic view. The hotel also boasts an outdoor swimming pool.
Day 2 Volterra to Castelvecchio near Pignano 17km/5 hours
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, then dropping down into the valley of the Era Morta. Here you join a gravel road that ascends steeply to the Villa Palagione, where you can sit in the shade with a cool drink and perhaps eat your picnic lunch or visit the Italian sunken garden. The old villa sits beside the steep and somewhat overgrown Monte Voltraio. A paleontologist’s dream as the ground appears to be scattered with fossils. The way onward follows a broad winding, often cypress lined panoramic ridge. Reach the pretty hamlet of Pignano and continue on a final leg to a road junction and onward to your lovely rural accommodation. Accommodation: Your evening is spent in a charming agriturismo. It has 12 rooms all of which are ensuite. Enjoy homemade jam with your breakfast and dinner is taken with the other guests and your host Emma tonight, this is a wonderful way to enjoy Italian hospitality. If you arrive early enough then take advantage of the swimming pool. Note: In busy periods we might need to organise some transfers back to Volterra for a second night as the number of rooms is limited.
Day 3 Castelvecchio near Pignano to San Gimignano 17km/4-5 hours
You soon leave the road and descend through interesting forest including several species of oak and strawberry trees. Next walk between vineyards of the famous Vernaccia de San Gimignano estates and through oak woods with wild cyclamen in flower in autumn. You continue to the pretty village of San Donato and the small hamlet of Montauto with fine views of San Gimignano, before 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. Overnight in San Gimignano. Accommodation: We stay at San Gimignano where our 3-star hotel is set in the pulsating heart of the town of towers, little changed for 600 years.
Day 4 San Gimignano to Colle Val d'Elsa 12km/4 hours or 18.2km/5 hours
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 we 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 pilgrim church of Badia a Coneo for a picnic, although this is often closed. The fascinating old town of Colle Alto occupies the crest of a ridge high above the valley of the Elsa. Overnight Colle Val d’Elsa. Accommodation: The BB Arnolfo is in the centre of Colle val d’Elsa. It has 10 rooms all of which are ensuite. They are all beautifully decorated.
Day 5 Colle Val d'Elsa to Monteriggioni 17km/5.5 hours
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 an Isola you should stop to see the abbey church. Eventually 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: Here we use various rooms within the medieval walled village of Monteriggioni; once the day-visitors have gone it is a haven of peace; the rooms (limited in number) are simply furnished, but all have private facilities.
Day 6 Monteriggioni to Siena 20km approx/5.5 to7 hours or to Il Ceppo 8.2 km/2.5 hours
Today you have the option of walking directly into Siena on a complete section of the 'Via Francigena' - the ancient pilgrims route to Rome, or a shorter walk via the hamlet of Il Ceppo where there is a great restaurant (closed Tuesdays) then take a taxi or 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 famous centre of this medieval city. There are many museums, churches, and the huge Pisa 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 from where the Sienese population gain their group loyalties and rivalries. Overnight Siena. Accommodation: In the lively and sophisticated city of Siena we stay at a small, comfortable town hotel (3*) in rooms with en suite facilities, telephone, and TV.
Day 7 Siena to Radda-in-Chianti 13km/4 hours
Starts with a taxi ride to the village of San Sano (included in tour price). From here we walk on white roads, farm and woodland tracks across undulating hills, covered with a patchwork of oak woodland, olive groves and 'Chianti Classico' vineyards to the hill-top town of Radda-in-Chianti. Overnight Radda-in-Chianti. Accommodation: We spend two nights in the small hilltop town of Radda in Chianti. A friendly welcome awaits you in this comfortable guesthouse which has its own wine bar.
Day 8 Circular walk from Radda-in-Chianti to Gaiole-in-Chianti 15km/5.5 hours
A circular walk of about 15km, 9.3 miles / 5.5 hours from Radda-in-Chianti to Gaiole-in-Chianti and back, taking in the attractive villages of Vertine and Selvole. You may be tempted en route by the plentiful, luscious vineyards and succumb to the delicious local Chianti, for which the region is famous. Overnight Radda-in-Chianti. Accommodation: We spend two nights in the small hilltop town of Radda in Chianti. A friendly welcome awaits you in this comfortable guesthouse which has its own wine bar.
Day 9 A choice of two walks
Today there is a choice of 2 routes of differing lengths, all finishing at the delightful hill town of Panzano. Starting in each case at our accommodation in Radda the longest of the routes goes through the fascinating borgo (fortified village) of Volpaia and across the heathland and pine forest of Monte San Michele, the highest hill in the Chianti region, before a long descent past several delightful hamlets to thewell known hill village of Panzano with its inspiring church and castle, from where you catch a bus to the valley town of Greve-in-Chianti. (13 km, 8 miles / 4.5 hours). The shortest route takes a direct line past the pieve (isolated church and sanctuary) of S. Maria Novella and the vineyards of Castelvecchio to Panzano. From Panzano it is only a 10 minute bus ride to Greve-in-Chianti, another centre of winemaking and the birthplace of Giovanni di Verrazzano who first circumnavigated Long Island, New York. Overnight Greve inChianti. Accommodation: In Greve we stay in a 3* hotel near the centre.
Day 10 Bus from Greve to Florence, about 1 hour (fare not included)
You will need to take your luggage on the bus with you. The rest of the day is free for you to explore this beautiful city at your leisure. Or you can do a walking excursion from Fiesole to Settignano (6-7 km, 2 hours). This is a panoramic walk through olive tree fields overlooking Florence and some of the most beautiful villas surrounding the city. Fiesole alone is worth visiting as it is an important archaeological site and has a Franciscan monastery. Overnight Florence. Accommodation: In the busy city of Florence we use one of a number of 2* hotels depending on availability at the time of booking.
Day 11 End of tour
Depart after breakfast and take train from Florence to Pisa (approx 1 ½ hour) for your flight home.