Classic Tuscany Guided Walk

Classic Tuscany Guided Walk

Trip Highlights

  • 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

Trip Summary

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 the base for most of the trip, walk in the company of your guide along sections of the Francigena Way. Visit 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.


The walking is graded moderate with 4 to 5.5 hours walking each day over hilly to steep terrain (the 2.5 hrs walking on day 2 is town walking). There are numerous hills in Tuscany and your preparation should include climbing and descending steps. A reasonable level of fitness is required. As with all of our trips it is important that you are well prepared. We suggest that you undertake regular exercise – swimming, cycling, stair walking and jogging, two to three times a week for three months prior to your departure.


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.

Meals:  D

After breakfast there will be guided visit of the historical centre of Florence. Later in the day, transfer by private minibus (1hr) to San Gimignano. Set on a hill at 324m altitude and dominating the 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 set 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 old centre and we'll admire the towers at sunset. Dinner and overnight in hotel in San Gimignano. Ascent +100/328ft, descent -100m/328ft, 6km/3.7mi

Meals:  B,L,D

Today you will discover the amazing landscape surrounding San Gimignano. Following ancient paths and the typical "white roads", today's walk will lead us between small Romanic churches and chapels, lush forest of chestnuts, and spectacular fields and vineyards. Wild boar and pheasant inhabit this area, close to small villages built of local stone and wood. During the hike there will be an olive oil and wine tasting. Olive oil is a Tuscan speciality. Overnight in hotel in San Gimignano. Ascent +550m/1805ft, descent -550m/1805ft, 13km/8mi

Meals:  B,L

The Via Francigena is a pilgrimage route which leads from Canterbury to Rome. Today's walk follows a gentle but hilly trail to Colle Val d'Elsa, an interesting and strategically located town in the heart of Tuscany, close to the cities of Siena, Florence and Volterra. From the early 13th century, trades that relied on water as a resource, such as flour and paper mills, flourished here, though it is now known for its production of lead-crystal glass. Private transfer (30min) to Radda in Chianti, in the heart of the superb Chianti wine region. Dinner (organic food) and overnight stay in agriturismo in Radda in Chianti. Ascent +370m/1214ft, descent -310m/1017ft, 13km/8mi

Meals:  B,L,D

This is a land of ancient wine making traditions of which there are Etruscan and Roman remains. The first documents identifying Chianti and its wine production date from the 13th century and refer to the Chianti League, founded in Florence. Starting from the agriturismo, we embark on a circular walk and see the ancient vineyards and the cultivation techniques. At the end of the walk there will be a wine tasting of typical Chianti wines. Dinner and overnight in Radda. Ascent +400m/1312ft, descent -150m/493ft, 15km/9.3mi

Meals:  B,L,D

After breakfast there will be a short transfer (30min) to Monteriggioni. This walled village with 14 perfectly preserved towers dominates the countryside from its hilltop position. Today's walk again follows 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/1148ft, descent -300m/985ft, 20km/12.4mi

Meals:  B,L,D

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 Duomo dating from 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 confectioners' shops. The trip arrangements conclude after breakfast.

Meals:  B

What's Included

  • 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.
  • 4 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 & wine tasting on day 3, wine tasting on day 5
  • English speaking guide throughout
  • Transfers by public and private buses as described
  • Guided visit of Florence (day 2)

What's Not Included

  • Travel to and from Florence / Siena
  • Beverages, lunch on days 1 and 7, dinner on day 3
  • Hotel taxes
  • Items of a personal nature
  • Entrance fees to sites and museums
  • Travel insurance

Upcoming Travel Dates


Guide made trip a pleasure, could joke and have an enjoyable time, helped in every way he could, very good knowledge of the areas inside and outside towns visited.

H.Richardson, WA. Australia

Tremendous adventure walking the Via Francegina between Florence and Sienna with a knowledgeable, experienced, entertaining and highly competent guide.

F. McGinty, Western Australia, 14 Oct 2016

For me it was an opportunity to enjoy the countryside without concerns about food, route or accommodation. Walking in a small group was a great pleasure as we were all similarly minded people. The guides provided points of interest about the localities, plants, customs etc. and interacted with fellow walkers who were often also knowledgeable about certain aspects. We had great fun and everyone managed the walk well.

B. Hughes, Lucca, Italy, 07 Jun 2017

Following a tour by World Expeditions to Macchu Picchu in 2011, I had no hesitation in taking part in the Guided Classic Tuscany Walk. The number of fellow walkers was nine; one leader and one assistant leader. It was an amazing group of like minded travellers who shared the same sense of humour and fun. I would gladly take part in another of these walks.

M. Koch, Aspley, QLD, 30 May 2017

This was a fabulous experience in one of the most beautiful places in the world, but you need to be reasonably fit to appreciate the surroundings. Absolute picture perfect scenery, picnic lunches in the most surprising places, and to walk into Sienna main square at the end was a joy. Well done Marta and Utracks. Would highly recommend.

M. Murphy, Castlemaine, Australia, 30 May 2017

This was a fantastic trip at a relaxed pace walking through amazing scenery. The food was fabulous and our guide, Riccardo, was extremely knowledgable and patient with all my nature questions! Overall it was a wonderful holiday which left me not wanting to come home. Will definitely be back on another tour!

E. Cathcart, Edinburgh, Scotland, 10 Oct 2017


Duration:7 Days
Starting Point:Florence
Finishing Point:Siena
Activities:GUIDED WALK
Grade:moderate  Click for more information
Trip Code:CTG
Prices From:GBP£1290 Per Person
Single Supplement:GBP£260  Click for more information
Please do not book any flights or extra arrangements until such time that your booking is confirmed by Sherpa Expeditions by phone or email.