Walking in Southern Tuscany

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Trip code: 
Way to Travel:
Self-Guided Walking
Min age:

Siena, Buonconvento, Sant'Antimo and Montepulciano

In the south-east of Tuscany the views change with the seasons; green meadows in spring, yellow wheat in summer and red leaves in autumn. This trip gives you an opportunity to enjoy the famous landscape, along with its beautiful abbeys, mediaeval castles and world-famous wines produced in the region. The walking each day takes in traditional Renaissance towns with stunning architecture and allows the exploration of the fertile Tuscan area, with expansive views over the rolling terrain and hill-top villages. The mouth-wateringly delicious cuisine is hearty and fresh and the wines are world renowned.


  • Charming villages and mediaeval fortresses
  • Stunning Tuscan landscapes
  • Hearty cuisine and world famous wines

Key information

  • 6 nights 3-star accommodation, all rooms en suite
  • 5 days two-centre walking with luggage transfers
  • Low altitude throughout
  • 7 days land only
  • Self-guided trip; min. age 10 yrs

What's included

  • All breakfasts and 2 dinners
  • All accommodation (see accommodation section)
  • All luggage transfers

What's not included

  • Travel insurance
  • Visas or vaccinations
  • Arrival & departure transfers (available on request)
  • Single accommodation (available on request) Compulsory supplement
Call us on
0208 772 3936
Trip Notes

Click on the button below for detailed Trip Notes containing all the particulars about this trip, including kit lists and practical information.

Note: these can vary by departure; you can check out the specific Trip Notes for your chosen adventure on the dates & prices page.



The terrain and type of path will vary between manmade paths, country tarmac roads and some mule tracks.

Day by day breakdown
Day 218.0km/11.0miles
Day 320.0km/12.0miles
Day 420.0km/12.0miles
Day 516.0km/9.0miles
Day 611.0km/6.0miles
Day 75.0km/3.0miles

Responsible Travel

At Exodus we believe in the power of Responsible Travel.

Every time we travel, we are part of a global movement that creates jobs, builds more sustainable societies, encourages cultural understanding and safeguards common natural and cultural heritage. To learn more about what Responsible Travel means to Exodus click here… 


  • Day 1

    Start Siena.

    Make your own way to Siena and spend the night in this beautiful city, with mediaeval charm and a historical city centre.

  • Day 2

    Train to Buonconvento; trek along the famous 'Crete Senesi' which give the landscape an almost lunar appearance; visit the Abbey of Monte Oliveto.

    This morning take a short train ride to Buonconvento. Drop your luggage off at the hotel, then trek along the famous 'Crete' (clays) to reach the Abbey of Monte Oliveto where you can visit the cloister with its renowned frescos. Along the way there is a chance to visit the castle of Monterongriffoli, and the tiny village of Chiusure. From Monte Oliveto Abbey take a private transfer back to your hotel for dinner.

    Walk approx. 18km, ascent 370m, descent 120m

    Meals included: Breakfast Dinner
  • Day 3

    Walk through beautiful vineyard-covered hills; visit the Priori's Palace, the Loggia and the Rocca, a pentagonal defence fortress built in 1361.

    Today, trek through the wonderfully scenic hills dotted with the famous Brunello's vineyards, and pass some beautiful private villas and cellars. Arriving in Montalcino you will have an opportunity to taste some of the excellent local wine, before visiting the Priori's Palace, the Loggia, the Sant'Egidio church and the Rocca: a pentagonal defence fortress built in 1361. Take a public bus back to Buonconvento.

    Walk approx. 20km, ascent 480m, descent 100m.

    Meals included: Breakfast Dinner
  • Day 4

    After a private transfer to Sant'Antimo, enjoy an incredible panorama from above the Orcia river. Arrive in Bagno Vignoni; public bus to Montepulciano.

    Morning transfer to the Abbey of Sant' Antimo set in a valley of vineyards overlooked by the town of Castelnuovo dell'Abate. From here, cross the Crete region enjoying magnificent views, before reaching the castle of Ripa d'Orcia and an amazing panoramic view of the area. Walk onwards to Bagno Vignoni; a thermal resort established in the middle ages. The village has a thermal bath in its main square (don't forget your swimsuit!). Walk to San Quirico D’Orcia before taking a public bus to Montepulciano.

    Walk approx. 20km, ascent 540m, descent 460m

    Meals included: Breakfast
  • Day 5

    Lose yourself in the streets of mediaeval Monticchiello, visit the Renaissance town of Pienza; bus back to Montepulciano to taste the famous 'Vino Nobile'.

    This morning the walk begins from Montepulciano, as you head through typical South Tuscan countryside with gentle hills and winding country roads dotted with Cypress trees and olive groves. Enjoy a lingering lunch or maybe a wine tasting in the mediaeval village of Monticchiello before a climb to Pienza, a great example of a typical preserved Renaissance village, and a UNESCO World Heritage Site. Spend some time enjoying the traditional architecture before taking a public bus back to Montepulciano.

    Walk approx. 16km, ascent 350m, descent 200m

    Meals included: Breakfast
  • Day 6

    Walk along the 'Crete Senesi' landscape, reach San Quirico d'Orcia; a charming town located on the Francigena Way. Bus back to Montepulciano.

    This morning take a public bus to Pienza before walking once more across the typical 'Crete Senesi', where the distinctive grey colour of the soil gives the landscape an appearance often described as lunar. Walk by small churches and farmhouses, and end in San Quirico d'Orcia, a village which is located on the Francigena Way. Take some time to visit the wonderfully romantic Collegiata (church), the typical Italian Garden of Horti Leonini and the antique town walls.

    Walk approx. 11km, ascent 200m, descent 250m

    Meals included: Breakfast
  • Day 7

    End Montepulciano.

    Today is your departure day, but if you have time we recommend taking a walk through the town of Montepulciano to enjoy the Renaissance arcitechture, and maybe take a wine tasting in one of the many cellars. From Montepulciano you can take a bus to Siena, Florence or Chiusi.

    Meals included: Breakfast
Trip Notes

Click on the button below for detailed Trip Notes containing all the particulars about this trip, including kit lists and practical information.

Note: these can vary by departure; you can check out the specific Trip Notes for your chosen adventure on the dates & prices page.

Essential Info



No visa required for British passport holders.
Please note in Italy it is compulsory to carry ID with you at all times.



There are no specific health risks.

Eating and Drinking

Tuscan food is based on the Italian idea of 'cucina povera' (poor cooking); simple inexpensive meals that can be made for large groups. Whilst this was once dictated by the economy and expense of the produce, the tradition has remained. The cuisine of this region doesn't use complicated seasonings or elaborate recipes, and instead focuses on fresh, high quality ingredients that allow the natural flavours in each dish to shine through. Typical dishes include fagioli con salsiccia (cannellini beans with sausage), tagliatelle al tartufo (pasta in a truffle sauce) bistecca Fiorentina (a T-bone steak often large enough to share!), pici (a fat, handmade spaghetti, often served with tomato and garlic sauce or game meat). Don't miss the local cacio and pecorino cheeses, and sample the famous wines: Nobile di Montepulciano and Brunello di Montalcino.


April and May departures can expect warm days, although rain is always possible. Nights may still be rather cool. Early June is similar, with the days becoming progressively hotter and the evenings much warmer. September and October are cooler and wetter, yet visibility is usually better. We strongly recommend a fleece-lined jacket or warm sweater in May, September and October.

Is this trip for you?

This is a self-guided tour; you can walk at your own pace (we recommend taking your time and enjoying the sights!)

Activity Level: 3 (Moderate).
Average daily walk: 17km (11 miles)
No. of days walking: 5 full days and 1 optional walk on the final day
Terrain & route: The terrain and type of path will vary between manmade paths, country tarmac roads and some mule tracks.
All walks take between 4 and 5 hours including lunch stops and require a moderate level of fitness. Please be aware that this area can be very warm, possibly exceeding 30 degrees in the summer.
Vehicle Support: This is a self-guided trip for those who prefer to walk independently, but with our assistance to take out the stress of the logistics and planning. We arrange your accommodations, provide you with route notes so that you can walk at your own pace, while your bags are transported from one hotel to the next. A representative will be there to meet you and will be on call throughout the trip should you need.

As this is a self-guided holiday there is no group and no leader. There may be others on the same departure date as you, but you will not be organised together. The route notes contain an emergency assistance telephone number should you need it and in emergencies, the local representative is normally able to dispatch a taxi or pick you up themselves. They may wish to charge for this service.

Call us on
0208 772 3936
Trip Notes

Click on the button below for detailed Trip Notes containing all the particulars about this trip, including kit lists and practical information.

Note: these can vary by departure; you can check out the specific Trip Notes for your chosen adventure on the dates & prices page.



6 nights in 3-star hotels, all rooms en suite. In Siena we use a hotel very close to the city centre. In Buonconvento we use a family-run hotel, and meals are taken in a restaurant run by the same family. In Montepulciano the hotel has an indoor swimming pool and a small wellness centre, and in Siena you are free to use the pool of the sister hotel.

All prices are based on 2 persons sharing, so if there is an odd number of people travelling in your party or you are travelling alone, there will be a compulsory supplement for a single room for the tour duration.
For a solo traveller there is an adttional charge to cover transfer costs.

Additional Accommodation

Extra accommodation is available in Siena and Montepulciano, please speak to your sales consultant for more details.

Call us on
0208 772 3936
Trip Notes

Click on the button below for detailed Trip Notes containing all the particulars about this trip, including kit lists and practical information.

Note: these can vary by departure; you can check out the specific Trip Notes for your chosen adventure on the dates & prices page.

Expert Blog Entries

  • Reviewed July 2017
    Danny Bell

    Self-Guided in Tuscany

    Great food, great wine and beautiful rolling Tuscany scenery. A lovely place for a relaxing weeks walking.

    What was the most inspirational moment of your trip?

    Most of the old historic towns are set on hills that gave great views out towards the surrounding countryside. Montepulciano was in particular a highlight of these little towns.

    What did you think of your group leader?


    Do you have any advice for potential travellers?

    Make sure you take notice and are up in time for the morning train from Siena to Buonconvento at the start as after that the next one is not until around midday.

    Is there anything else you would like to add?

    Would like to say thank you in particular to the staff at the third hotel in Montepulciano as they were so lovely and welcoming all round. :)

Dates & Prices

An overview of flight options

Exodus is committed to making joining our tours as easy as possible, wherever you live. We generally only block book seats from London, but this certainly does not mean that you need to fly from there. Depending on the route and airlines available, there will usually be various options available for those who want to fly from their local airport.

This page aims to provide a useful overview of the options available to our clients. However, the best flight arrangements should be tailored to your personal requirements, so please contact our Sales team for expert advice.


What kind of options do I have ?

1. We can book for you: Flights from anywhere in the world - not via London  

Depending on the route, this may be direct or via an overseas hub like Amsterdam, the Middle East or elsewhere. On short haul routes there may be direct flights with low cost airlines, charter flights or scheduled airlines. Exodus can book most, but not all, of these for you. The most appropriate airline may be different to that which we use for the group flight from London, but many people now travel on different airlines and meet up with their fellow passengers at the destination.

Pros Cons
  • May be the most direct route
  • Often the extra fare compared to the London flight is minimal.
  • As you will be in the hands a single airline for your entire journey, the airline will be responsible for your bags and your connections.
  • You may not be able to join the group transfers. However, we can usually arrange private transfers, or book your flights to try and coincide with the group transfers. See notes on transfer arrangements below.


2. We can book for you: Connecting flights from your local airport to London

Exodus can book connecting flights to London so you can join the group flight there. Connecting times will be followed according to airline advice, or as requested by clients. There are two types of fares we can use for this option: a 'through-fare' or a 'published fare'.
a) A 'through-fare' is where you will be in the main airline's care throughout. You change planes, but your bags are checked all the way through to your final destination. 

b) A 'published fare' ticket is completely seperate from your onward ticket from London. It is usually cheaper than a through-fare but will need to be paid for and issued as soon as it is booked. This can be a problem if your tour has not yet reached minimum numbers. On 'published fares' neither airline is aware that you have connecting flights, so Exodus is responsible for timing your connection, not the airlines involved. The tickets are also usually non changeable and non refundable.

Pros Cons
  • Depending on the fare type, Exodus or the airline is responsible for flight connections.
  • Through fare tickets can be expensive.
  • On a published fare, tickets must be issued immediately; tickets on published fares can be very difficult to change if onward flight times change; bags are not checked though to your final destination.
  • Published fares are non-refundable.


3. Booking some or all of the flights yourself

You can also book connecting air travel yourself, either to London, or all the way to the start point. There may be certain airlines or routes we don't have access to, so this is always an option. However, if you make your own travel arrangements you become liable for any delays, cancellations or missed connections, and Exodus is not required to offer refunds if you have trouble reaching the start of your trip.

Pros Cons
  • You might find cheaper fares, or routes not available to Exodus.
  • You are responsible for any delays or missed connections, and the cost of the tour is not protected should you miss your flight be cancelled.


 Notes on transfer arrangements

Sometimes it is possible to travel on a different airline to the group flight from London. Where this is the case, we need to think about ensuring you meet up with the group with minimum extra cost and hassle.

  • On certain trips, it is easy to arrive on a different flight and still meet the group at the hotel with time in hand. We can usually arrange private transfers (at extra cost) or offer advice on taking a taxi to the start hotel.
  • On other trips (especially in Europe), the transfer meets the group flight and then travels some distance to the first night's accommodation. Where this is the case, our Sales team will try to arrange flights that arrive before (and depart after) the group. However, we do have to make it clear in your final documentation that if your flights are delayed, the transfer cannot wait for you. While Exodus or our local operators will do what we can to help you reach the start point of the tour, any additional costs must be paid by the client. 


Next steps? 

Call our Sales team on: 0203 733 0698

Email your query: [email protected]

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Call us on 0208 772 3936