Classic Tuscany Guided Walk

Classic Tuscany Guided Walk information and booking

  • Duration
    8 days
  • Group size
  • Difficulty
Check prices & availability

Schedule Details

  • 5 nights 3 star hotel, 2 nights charming Agriturismo
Equipment Required
Wet weather gear, sunscreen, headtorch, gaiters, good walking boots and sun hat - walking poles optional but recommended. A comprehensive gear list is included in the pre-departure information provided on booking.


  • Historical towns of Siena and Florence
  • San Gimignano, Colle Val D'Elsa and Monteriggioni: the Tuscan medieval jewels
  • The Chianti region: the wine, art and history
  • Tasting the typical Tuscan cuisine and organic food at the Agriturismo

Tour description provided by World Expeditions

From Piazza della Signoria to Piazza del Campo, an inspirational guided walk joining two of the most important Tuscan cities. Between Florence, the city of Leonardo, Giotto, Dante and Brunelleschi, and Siena, native land of the "Palio" lies the Chianti wine region, an area of rolling vine covered hills, medieval villages and olive groves. The region is ideal for exploring on foot, experiencing the slower pace of life endemic to Tuscany and learning about the long history of wine making. From San Gimignano, a town dominated by its magnificent towers and our base for most of the trip, walk in the company of our guide along sections of the Francigena Way, visit Volterra famous for its alabaster handicrafts and the fortress village of Monteriggioni. Spend two nights at a charming agriturismo in the heart of the Chianti wine region before making the last stage of the journey on foot to Siena. Ample opportunity is set aside to visit markets, taste wine and olive oil, explore the narrow streets of small towns and visit museums, galleries and vineyards en route.

What's included

  • 7 breakfasts, 6 lunches, 5 dinners. breakfasts are usually continental inclusive of breads, tea, coffee & juices. lunch will be picnic style often consisting of bread with meats, cheeses and salad. dinner will consist of 3 courses, usually starting with a salad, followed by a chicken, red meat, fish or pasta dish & finishing with a dessert of fruit or cakes.
  • 5 nights 3 star hotel, 2 nights charming agriturismo - accommodation on a twin share basis with ensuite facilities (hotel taxes extra, payable locally - allow €10-15)
  • Olive oil tasting on day 3, wine tasting on day 6
  • English speaking guide throughout
  • Transfers by public and private buses as described


Day 1 Arrive Florence
On arrival in Florence, make your way to the group hotel. The tour guide will meet you at the hotel in the afternoon. Dinner in a restaurant and overnight in hotel.
Day 2 Transfer to San Gimignano, explore town and surrounds (2hrs)
After breakfast there will be a short visit of the historical centre of Florence. Then transfer by public bus (1hr 30min) to San Gimignano. The town is set on a hill at 324m altitude and dominates the whole Val d'Elsa: it is a beautiful example of a medieval town that has remained intact despite modern development. The numerous towers are a defining feature that sets it apart from other towns. Enclosed within its 11th century walls, the town is built along two axes which intersect: from east to west from the tower in Poggio to Poggio Montestaffoli and from north to south along the axis that goes from Porta San Giovanni to Porta San Matteo, where it follows the Via Francigena. This afternoon there will be a gentle walk in the surrounding fields and vineyards, with time to admire the sunset. Dinner and overnight in hotel in San Gimignano. Ascent +100, descent -100m
Day 3 Circuit through classic Tuscan countryside (4hrs)
Today we'll discover the amazing landscape that surrounds San Gimignano. Following ancient paths and the typical "white roads" our walk will lead us between small Romantic churches and chapels, lush forest of chestnuts, and spectacular fields and vineyards. At the end of the walk, there will be a special olive oil tasting. Olive oil is a Tuscan speciality. Overnight in hotel in San Gimignano. Ascent +150m, descent -150m
Day 4 Explore Volterra and surrounds, return to San Gimignano (3hrs)
Transfer by public bus (30min) to Volterra. Hike around the hills of Volterra to discover the hidden corners of this region. We will see a variety of different landscapes, and come to appreciate the surrounding cliffs and the Etruscam necropolis. In the afternoon we will explore the city of Volterra. This small medieval town is definitely a milestone for any trip to Tuscany, both for its atmosphere and its historical riches. The town rises to 545m of an impressive wall of limestone and clay. Return to San Gimignano by public bus. Overnight in hotel. Ascent +300m, descent -300m
Day 5 Walk the Via Francigena to Colle Val D'Elsa, transfer to an Agriturismo in Chianti (4hrs)
The Via Francigena is a journey of history, a pilgrimage which leads from Canterbury to Rome. We will follow a gentle but hilly trail to Colle Val D'Elsa, an interesting town located in the heart of Tuscany, in a strategic position, close to the cities of Siena, Florence and Volterra. Colle Val D'Elsa is known for the manufacture of glass and the production of lead-crystal glass. Private transfer (30min) to Castellina in the heart of the superb Chianti wine region. Dinner (of organic food) and overnight stay in Agriturismo. Ascent +370m, descent -310m
Day 6 Explore Chianti on foot (4hrs)
The Chianti is a land of ancient winemaking traditions of which there are Etruscan and Roman remains. Starting from our Agriturismo we will embark on a circular walk. En route we will see the ancient vineyards and the cultivation techniques. At the end of the walk there will be a wine tasting of the typical Chianti wines. Dinner and overnight in Agriturismo in Castellina. Ascent +400m, descent -400m
Day 7 Transfer to Monteriggioni, walk the Via Francigena to Piazza del Campo in Siena (5hrs)
After breakfast there will be a short transfer (30min) to Monteriggioni. This walled village with 14 perfectly preserved, dominates the countryside from its hilltop position. Today we will again follow the Via Francigena, along a section considered to be one of the best walks in Italy. Arriving on foot in the Piazza del Campo in Siena is an unforgettable experience. Dinner and overnight in hotel in Siena, with time to explore this fantastic city. Ascent +350m, descent -300m
Day 8 Trip concludes in Siena
Siena is a classic hilltop town with impressive monuments, such as the Buonsignori Palace with its National Picture Gallery, the white and dark green marble decorated Dome dating back to the twelfth century, the Piccolomini Library, the Baptistery and the Museum of Metropolitan Opera. you can visit these terrific sites or simply enjoy a stroll around Piazza del Campo and along the narrow streets, stopping for a taste of Panforte and Ricciarelli in some of the typical confectioner’s shops. The trip arrangements conclude after breakfast.