Tuscany Uncovered

Tuscany Uncovered

Trip Highlights

  • Visit famous Mediaeval towns on the Via Francigena on foot
  • Possibilities for wine tasting and Tuscan cuisine
  • Walking on quiet trails throught the tuscan countryside

Trip Summary

The emphasis of this holiday is for you to enjoy yourself! Based in the beautiful fortified village of Monteriggoni, at the medieval border between Siena and Florence, the village is on the Via Francigena and on the edge of the Chianti wine district. You can do as much or as little as you like. We provide you with a series of walks that you can do each day. You could do a combination of walks as well as relaxing in the village, or using bus connections, visit Siena or San Gimignano and visit the museums. The general length of the walks varies from 8.5 km to a hilly 31 km challenge, the latter can be shortened to do over two days. Due to its very nature, all the walks involve some hills, and in Tuscany these can be quite steep. Wine tasting in Chianti is a possibility on a couple of the walks and there is great scope for eating at fine restaurants. Extra nights can easily be added should you require them.


Easy to Moderate. Hilly at times. Fitness: Super fitness is not necessary but you should be able to walk for up to 7 hours a day in hot sun on dusty and stony tracks. There are some steep hills on this tour, but nowhere could the terrain be described as mountainous.


You will need to travel to Siena or Poggibonsi-Monteriggioni to be picked up by our agent who will transfer you to the small village of Monteriggioni. There is normally at least one train an hour from Pisa Centrale to Poggibonsi, in each case you will need to change at Empoli. The journey takes about 1.5 hours. Monteriggioni represents one of the most important walled castles in the area. It has incredibly preserved an intact structure as if time had never passed on the hill from which it elegantly dominates the surrounding landscape. The castle was built by the Sienese between 1213 and 1219 for defensive purposes: its strategic location atop a hill overlooking the Cassia Road allowed the castle to control the cities of the Val d’Elsa and Staggia and be on the lookout for any armies approaching Siena. The intact fortified wall presents 14 towers along which the guards used to walk and patrol the walls and 2 gates, one called the Franca or Romea Gate which faces Rome and the other known as the Florentine Gate since it heads toward Florence. The current structure of the village is essentially the original one, the only changes it went through date back to the 16th century when the towers were lowered. Accommodation: La Signoria 1212. Il Piccolo B&B in Monteriggioni offers accommodation in Monteriggioni. The rooms are equipped with a flat-screen TV the rooms come with a private bathroom. La Signoria Piccolo B&B features free WiFi throughout the property. You will find a shared lounge. You may wish to upgrade to a 4 star inn, ask for details.

Meals:  B,D

An interesting walk to Siena arriving at the Camollia Gate, where pilgrims for centuries passed through and into the heart of the city. The route is generally well waymarked with people walking sections of the Via Francigena, the ancient pilgrimage route from Northern Europe to Rome. There are shady woodland sections, but also sections where you are exposed to the sun. Once in Siena, you should have time to look around, before taking a train back to Monteriggioni. If you would like more time in Siena, there is also a shorter option to Il Ceppo Distance: 8.2 km approx. Walking time: 2.5 hours not on the Via Francigena. You can you have lunch and then get a taxi onto Siena (restaurant has been closed on Tuesdays).

Meals:  B

The Chianti Classico district stretches between the hills between Florence to just a few kilometres before Siena. This is the defined area where wine producers can use the prestigious black rooster or ‘Gallo Nero’ symbol on their DOCG (Guaranteed geographical domain) bottle foils and labels. This walk undulates along through some vineyard estates with opportunities for wine tasting. There is an option to make the walk shorter by about 5 km. The restaurant / enoteca at Lornano is a great place to stop for lunch.

Meals:  B

This can be split between two days, although strong walkers can complete it in a day. 4 hours to Colle Val d’Elsa and 9 hours approx all the way to San Gimignano. This is a great walk for small hamlets, old woodlands and some expansive views, especially with the towers of San Gimignano getting nearer and nearer. The walk all the way to San Gimignano is a long one and we may suggest that if you want some time to look round, that you do the walk to Colle today and then visit San Gimignano tomorrow. So instead of going to San Gimignano, you could walk all the way to Gracciano on the same route, then take the hourly bus to Colle val d’Elsa, see the upper town then return to Monteriggioni by bus, or to Poggibonsi and then train to Castelline and walk back to Monteriggioni.

Meals:  B

A whole day walking visit to San Gimignano to see it in depth. This is an obvious tourist towns, but is one of the best preserved medieval towns in Italy. We would recommend that you take the train to Poggibonsi from Casteline and then the bus to San Gimignano and make a day of it. The bus takes 20 minutes and there are up to two an hour. You should include visits to attractions like Sant Agostina, Piazza Cisterna, Piazza del Duomo, and La Rocca (fortress). It is a place of frescoes, towers, and gorgeous views across the Tuscan hills. A great place for tasting wine, gelati, souvenir hunting and having a good lunch before catching the bus and train back. You could of course get the bus or a taxi back to Colle and start the walk from Gracciano to San Gimignano, 16 km / 10 miles, 4-5 hours.

Meals:  B,D

Depart after breakfast. You will be transferred to Casteline or Poggibonsi to join the mainline train services.

Meals:  B

What's Included

  • 5 breakfasts, 2 dinners
  • 5 nights accommodation in village rooms
  • Arrival / Departure transfer from/to train station at Siena or Poggibonsi-Monteriggioroni
  • Transfer from Colle or San Gimignano after the walk
  • Information pack including route notes and maps (1 pack per room booked)
  • Emergency hotline

What's Not Included

  • 3 evening meals, lunches & beverages
  • Entrance Fees
  • Travel Insurance

Upcoming Travel Dates


Duration:6 Days
Starting Point:Monteriggioni
Finishing Point:Monteriggioni
Activities:Self-Guided Walking
Grade:Introductory to Moderate  Click for more information
Trip Code:JUC
Prices From:GBP£730 Per Person