Classic Tuscany Guided Walk
All content by World Expeditions
A classic walk from Florence to Siena through the magnificent Tuscan countryside
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 Colle Val d' Elsa, a lovely medieval village and our base for most of the trip, walk in the company of our guide along the Francigena Way to Saint Gimignano, a town dominated by its magnificent towers and Volterra famous for its alabaster handicrafts. Ample opportunity is set aside to visit markets, explore the narrow streets of small towns and visit museums, galleries and vineyards en route.
- Historical towns of Siena and Florence
- San Gimignano: an original approach from Colle val d’Elsa
- The villages of the Chianti region: Castellina and Radda in Chianti
- Soaking up the atmosphere in specially chosen hotels
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, following which there will be a short city tour with time free to visit Florence. Dinner in a restaurant and overnight in hotel.
Day 2 Transfer to Colle Val d'Elsa, explore town and walk to Colle Alta (4hrs)
After breakfast transfer by public bus to Colle Val d'Elsa where we begin our walk along the Via Francigena. At Colle Alta you can visit a crystal workshop in the tradition of the famous master craftsman Boreno Cigni. We spend time visiting Colle Val d'Elsa, the ancient city of Etruscan origin, allied with Florence against Siena in the 12th Century. Dinner and overnight in hotel. Ascent +150, descent -150m
Day 3 Transfer to Castellina in Chianti and walk through vineyards to Radda (4hrs )
Transfer by private minibus to Castellina in Chianti. The route passes through the vineyards and olive groves of Chianti Classico, along trails and unpaved roads in the heart of the Chianti region, up to Radda in Chianti. Sightseeing of the city and return by minibus to Colle Val d'Elsa. Dinner and overnight in hotel. Ascent +350m, descent -200m
Day 4 Walk to San Gimignano, visit town (4hrs)
From Colle Val d'Elsa we begin walking to reach the Abbey Cone, founded by the Benedictine rule around 1000. It subsequently came under the reform "vallombrosana" when it was consecrated in 1124 as the Church of Santa Maria Assunta, bishops of Volterra. Passing Molino d'Aiano along the Via Francigena we head 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. Return to Colle Val d’Elsa by bus. Dinner and overnight in hotel. Ascent +390m, descent -290m
Day 5 Transfer to Volterra, explore town and surrounds by foot (3.5hrs)
Transfer by public bus to Volterra. We hike around the hills of Volterra to discover the hidden corners and better appreciate the cliffs and the Etruscan necropolis. Sightseeing of the city: this small medieval town is definitely a must see for any trip to Tuscany, both for its atmosphere and historical riches. The town rises miraculously to 545m on an impressive wall of limestone and clay excavated by erosion. Return to Colle Val d'Elsa by bus. Dinner and overnight in hotel. Ascent +300m, descent -300m
Day 6 Transfer by public bus and walk to Monteriggioni, transfer to Siena (4.5hrs)
After breakfast short transfer from Colle Val d'Elsa by public bus to reach the start of the trek. Through the Val d'Elsa, we reach the village of Scorgiano, following a path that leads to the Castle Petraia converted into a residence in the 15th and 16th century. Visit the Cistercian monastery of the 11th century (fresco attributed to Duccio Boninsegna, baptismal funds of the 15th century) and the ruins of a fortified wall. Later we arrive in Monteriggioni, with its well preserved walls with 14 towers. Transfer by private bus to Siena. Dinner free and overnight in Siena. Ascent +280m, descent -250m
Day 7 Visit town, trip concludes
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.
- 6 breakfasts, 5 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.
- 6 nights in 3 star hotels on a twin share basis with ensuite facilities (hotel taxes may apply - payable locally)
- English speaking guide throughout
- Luggage transfer by public bus on day 2 and by private minibus on day 6
- Transfers by public and private buses as described
Group Size Min
Group Size Max
During your time in Florence, Colle Val d’Elsa and Siena you will be accommodated in 3 star hotels. All accommodation is provided on a twin or triple share basis with ensuite facilities.
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.