Far more than just a simple “Siena walking Tour”, this journey will combine emotions, charm, colour, and flavours that will change the way you see the world.

We start from the famous Piazza dei Miracoli in Pisa, with its Monumental Cemetery and Leaning Tower, and then set off to explore the real Tuscany, with its wealth of history, culture and natural wonders. We will cross the Magona nature reserve, with its centuries-old forests, a sanctuary for many species of birds such as the white stork which nests here, and we will venture through the unspoilt Monterufoli park, with its extraordinary Rivivo river.

We will discover the wines of the Ornellaia estate, tour its revered vineyards and taste its very best vintages. Afterwards, a gourmet dinner in the estate’s exclusive banquet room: a variety of specially selected courses and carefully paired wines.

Our journey continues to the historic town of Volterra, with its Etruscan roots, and San Gimignano, enclosed within its 12th century walls. These two gems, set amidst the Tuscan countryside, are certain to captivate with their rich earthy tones and unique local flavour. A stop too, at the tiny fortified village of Monteriggioni, encircled by its elliptical city walls, only 570 m long, but featuring 14 towers and 2 gateways. You might feel that time has stood still in these Tuscan villages whose strong ties with the land have modelled the landscape and created such spectacular scenery.

Siena is our next stop, its shell-shaped Piazza del Campo an elegant and harmonious space in the heart of the city. The city is divided into 17 Contradas whose boundaries were formally defined in 1729 by Violante Beatrice of Baviera, the Governor of the city. Each Contrada possesses its own church which houses all its historical Palio heritage including standards, costumes and archives.

After delving deep into Tuscany’s unique history and traditions, savouring its rich flavours and absorbing the warmth of its golden hues, you are bound to be tied forever in your heart to these special places of Italy.


Day 1 – In the shadow of the Leaning Tower – Meet your driver at Pisa or Florence Airport and transfer to hotel. Welcome meeting with participants and tour guides, and tour briefing. Dinner and overnight stay at hotel.

Meals: dinner.


Day 2 – Back in time. The Middle Ages and the Knights Templar

Our journey will start in Piazza dei Miracoli to admire the famous tower, take a look inside the cathedral and visit the Monumental Cemetery with a local guide.

Afterwards, transfer to Bibbona where we will check in to our accommodation, situated close to the Magona nature reserve. After a light welcome lunch, we will attend a cooking class, trying our hand at picking our own produce from the vegetable garden and using it to create some classic Italian dishes: pappa al pomodoro, pizza, schiacciata, fresh pasta and desserts. Dinner and wine tasting. Overnight stay at our hotel.

Meals: breakfast, lunch and dinner.


Day 3Countryside and wine. Bibbona to Bolgheri.

An early wake-up call is needed today, to give us time for a breakfast of fresh fruit and local produce before our meeting at 8.00 am to visit the Magona park, a WWF nature reserve. We will walk the hills and vineyards of the famous wine trail, reaching Bolgheri in the first part of the morning. Here we will visit one of the most famous wine estates, Ornellaia, and of course have a chance to taste their excellent wines, as well as their own olive oil and grappa. This will be followed by a special lunch on the estate, where the chef will prepare seasonal food combined with another selection of Ornellaia wines. After lunch there will be plenty of time to explore the quaint village of Bolgheri before returning to our hotel for a relaxing aperitif and dinner.

Dinner and overnight stay.

 Meals: breakfast, lunch and dinner.

Technical details for day 3:

Environment: slightly hilly landscape, Mediterranean scrub, vineyards and medieval villages

Grade: easy

Terrain: slightly undulating, park tracks, hunter’s paths, forest paths.

Distance: 12km

Time: 3h 30m

Elevation gain: 100 m


Day 4A castle, a village and Tuscan cuisine. Bibbona to Querceto.

After an al fresco breakfast, we will set off for Querceto, taking a route through the Magona scrubland, identifying Mediterranean plants on the way. Our accommodation in Querceto is a traditional inn where we will be served a medieval dinner, accompanied by local wines. Overnight stay in Tuscan style apartments.

Meals: breakfast, lunch and dinner.

Technical details for day 4:

Environment: Magona park, slightly hilly landscape, Mediterranean scrub, vineyards and medieval villages

Grade: moderate

Terrain: slightly undulating, paths, mule tracks, scrubland.

Distance: 15km

Time: 5-6 hrs

Elevation gain: 350 m


Day 5Travelling with the Etruscans -Querceto to Vicarello di Volterra.

From Querceto we will head into the Monterufoli nature reserve, walking through hilly landscapes of cypress, olive groves and vineyards. On the way, see some Tuscan villages, like Montegemoli, known for its homemade bread, where we will stop for a light lunch. Afterwards we head for Saline di Volterra from where we will travel by private transfer to the village of Vicarello di Volterra, in the real heart of Tuscany. On arrival we will settle into our rooms and, if we wish, try the hotel spa. Special treatments available by prior arrangement. We will have dinner at the resort, and a tasting of Bocelli wines.

Meals: breakfast, lunch and dinner.

Technical details for day 5:

Environment: Monterufoli nature reserve, hilly landscape, vineyards and olive groves, holm oak, elm, chestnut, ash, medieval hamlets

Grade: moderate

Terrain: undulating land, paths, tracks

Distance: 20

Time: 7-8 hours

Elevation gain: 300 m


 Day 6From tower to tower – Volterra to San Donato di San Gimignano.

We will start the day by visiting the historic centre of Volterra and the Etruscan Museum. After a light lunch at one of the best restaurants in Volterra, we will travel by private transfer to the beginning of the path which will lead us to the Castelvecchio nature reserve, named after the old medieval fortress. During the hike, observe the many species of trees and plants, such as Downy oak, Turkey oak, beech, and heather. After walking for about 10 km, we will come to the hamlet of San Donato where we can unwind over a tasting of organic Tuscan produce, wine and olive oil. Dinner will be prepared using the farm’s own produce.

Meals: breakfast, lunch and dinner.

Technical details for day 6:

Environment: Castelvecchio nature reserve, slightly hilly landscape, cypress, vineyards and olive groves, farmland

Grade: moderate

Terrain: undulating land, paths, mule tracks

Distance: 10 km

Time: 3 hours

Elevation gain: 150 m


Day 7From the Middle Ages to the Renaissance – San Donato to Colle Val D’Elsa, via San Gimignano.

From San Donato we will travel to San Gimignano by private transfer and here meet our local guide for a guided tour of the medieval town. After a light lunch at a famous restaurant in the town centre, we will walk along the famous Francigena pilgrims’ route which will lead us through stunning landscapes to Colle Val d’Elsa. Arrival at Colle Val d’Elsa and check-in at our hotel in the Renaissance village, followed by a welcome aperitif. Dinner at the hotel’s well-known restaurant and overnight stay.

Meals: breakfast, lunch and dinner.

Technical details for day 7:

Environment: Via Francigena, hilly landscape, forests of beech, strawberry tree and lentisk

Grade: moderate

Terrain: undulating land, paths, Via Francigena

Distance: 18 km

Time: 6-7 hours

Elevation gain: 200 m


Day 8Fortified towns of the Montagnola Senese – Colle Val d’Elsa to Monteriggioni.

From Colle we will continue our journey on foot to the fortified hamlet of Monteriggioni where we will find ourselves in the land of Chianti wine, horses and farming culture, and very close to Siena. Enjoy the extraordinary views from the village, and dinner at a local restaurant. Overnight stay at hotel.

Meals: breakfast, lunch and dinner.

Technical details for day 8:

Environment: hilly landscape, Mediterranean scrub, holm oak, strawberry tree, cistus, heather, olive groves and vineyards, medieval villages

Grade: moderate

Terrain: undulating land, paths, dirt and mule tracks

Distance: 15 km

Time: 5-6 hours

Elevation gain: 200 m


Day 9The Via Francigena - Monteriggioni to Siena.

After a hearty breakfast, we will begin our hike from the medieval hamlet, over the Montagnola Senese to Siena, along deserted roads, rich in history and charm. We will enter Siena through the Porta Camollia gateway, the historic access to the city on the Via Francigena route, and proceed to Piazza del Campo, where we can rest while taking in one of the most spectacular spots in the world. Transfer to our exclusive hotel. Dinner and overnight stay at hotel.

Meals: breakfast, lunch and dinner.

Technical details for day 9:

Environment: Montagnola Senese, Via Francigena, hilly landscape, holm oak, strawberry tree, lentisk, cistus, olive groves and vineyards, medieval villages

Grade: easy

Terrain: undulating land, paths, dirt and mule tracks

Distance: 20 km

Time: 6 hours

Elevation gain: 330 m


 Day 10Siena. A complete day to explore Siena.

We will start early in order to fully appreciate the atmosphere of Siena. Our private tour guide will accompany us along the city’s ancient streets, taking in museums and monuments of rare beauty. Lunch and the afternoon will be at your leisure. Meet again at the hotel for the presentation of your personal data sheets. Dinner at one of the most characterful restaurants in Siena, where the chef will prepare typical food accompanied by local wines.

Meals: breakfast and dinner


Day 11Departure. Private transfer to Pisa or Florence Airport.

Meals: breakfast.




RELAIS SANT’ELENA Dating from the 19th-century, this property is part of three splendidly-restored historic buildings situated in the rolling Tuscan countryside, just a short distance from the Magona Nature Reserve. It is the ideal setting for moments of relaxation and unique experiences, all in true Tuscan style.




BORGO VICARELLO DI VOLTERRA Vicarello di Volterra is a 15th-century village in the heart of the tranquil Tuscan countryside where history, culture and art form a natural setting. Situated in the centre of the Era valley, the historic residence is surrounded by landscapes synonymous with Tuscany: low hills covered in Mediterranean vegetation, vineyards, and olive groves, rows of tall cypress, farmhouses and fortified medieval villages. The village offers all the amenities necessary to make your stay a unique and unforgettable one, including a wellness centre with jacuzzi, sauna, Turkish bath, multi-sensory shower, and gym, and an open-air swimming pool with sun terrace.



FATTORIA SAN DONATO is a small medieval hamlet set among the green hills around San Gimignano and the Castelvecchio nature reserve. The hamlet grew up on the Via Francigena pilgrim route around a small Romanesque church and has maintained its original architecture: the fortified villa with its centuries-old park, the farm houses, and the guard tower which has been converted into a tavern for guests. The cuisine is based on homemade dishes and reflects Tuscan traditions.





PALAZZO SAN LORENZO Palazzo San Lorenzo is a prestigious palace set in the characteristic old part of the small town of Colle Val d’Elsa, a medieval gem in the heart of Tuscany where treasures of history, art, nature, food and wine surrounded by an unspoilt landscape are all waiting to be discovered.

Villa Tina Hotel














The NH Siena, formerly known as NH Excelsior, hotel is in a great place for tourists. A short walk takes you into the heart of Siena, with its wealth of historical landmarks, Gothic architecture and pavement cafés



Accommodation, food, transport

  • 10 nights at hotels of charm, luxury hotels, and historical properties.
  • All breakfasts, lunches as in the program, dinners as in the program
  • Transfer from Pisa Airport to the beginning of the tour
  • Transfer from the end of the tour to Pisa Airport
  • All transfers during the tour
  • Transfer, loading and unloading of suitcases
  • Back up vehicle, rescue support

Technical equipment and nutrition

  • Travel insurance
  • Trekking poles
  • Heart rate monitor
  • Services of a local specialized environmental guide throughout the tour
  • Downloadable GPS Files
  • Back-up nutrition: energy bars, mineral salts, dried fruit, all carried and distributed by your tour leader
  • Personalized data sheet


Cooking classes, museums, art cities, winery visits and tastings, events

  • One cooking lesson with dinner
  • Entrance to the Etruscan Museum of Volterra.
  • Guided tour of Pisa
  • Guided tour of Siena
  • Tour and tastings at the Ornellaia estate
  • Wine and oil tasting at the San Donato farm



  • Air fares
  • Extra Beverages
  • Personal Extras
  • Anything else not specified under “What’s included”


  • We can organize transport to arrival and departure points other than those specified in the tour.
  • It is possible to arrange hotel and guided tours in Florence, Pisa and Lucca before or after the tour.


Note: the tour is subject to variation in the event of bad weather or other unforeseen circumstances, at the discretion of the tour leader.

Walking level



Tour leader

  • IMG_0635

    Giuseppe Gaimari

    Technical manager of ITD Factory but above all a sports and nature lover. A competitive skier, I have always worn some kind of boots, whether they be ...


    Enrico Fruganti

    The journeys I have proposed have been conceived in order to show the age-old exchange between man and nature through the arts of agriculture, architecture, ...

  • Carlo Travagli

    Carlo Travagli

    Since 2004 I have been workin freelance in the wine world. I’m a consultant for many wineries mostly in the areas of Siena and Florence, in Cerreto ...


Length: 10nights/11days Cultural walking right at the heart of Tuscany


Per person based on 4 people in double room starting from 3300 euro


Through the woods and trails of protected natural areas , rich in flora and fauna The classic image of Tuscany postcard . For an experience totally Tuscan-style Cycling or walking along the famous "Via Francigena" , the old pilgrim route from Canterbury to Rome Experiences which will be given special attention to the world of wine from the vineyards , cellars and tasting , the dishes combined with the finest wines

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