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Hill Towns of Tuscany Highlights

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Walking Self-Guided Holiday

Active Travel Tuscan Experience

Tuscany, Italy
6 Days
€ 780 combadi price


Save €20 to €50 when booking via Combadi

Holiday Type
Open dates
Running Period
April to October on any day

The Combadi Insight:

If you are looking for a holiday to explore the beautiful Tuscany countryside, this walking holiday is your passport. Travel through vineyards, hills and olive groves, explore the medieval hill towns on route and enjoy the fine food and wine of the region. All these, in specially selected agrotourism and family run-hotels. Simply beautiful.

Holiday Code: AY1

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Few places on Earth have a cultural cache like the Tuscan countryside, and this self-guided walking holiday gives you an intimate view of the legendary region. Spend 6 days walking through Tuscany's lush vineyards, rich olive groves, and medieval hill towns.

The beauty of the region is perfect for a leisurely self-guided walking tour, as the landscape encourages exploration. This Tuscan travel experience provides guests with all accommodations and maps to guide them through their trip.

Your walking holiday of the Tuscan landscape begins at the medieval hill top town of Montepulciano, before continuing to the renaissance town of Pienza, a UNESCO world heritage site. On your way you'll be passing by many architecturally and historically fascinating towns and monasteries. Enjoy the generous Tuscan hospitality before your journey’s end in the wonderfully picturesque Crete region of Buonconvento. You'll also soak in the thermal baths at Bagno Vignoni and enjoy the fine wine and food that southern Tuscany has to offer!

This Tuscan hiking experience includes all room, board, and daily door-to-door baggage transfers, allowing guests to focus solely on enjoying their walking tour of the Tuscan countryside. The difficulty of the tour is rated as easy to moderate, and superior comfort offered by traditional local accommodations and agrotourism hotels that await for you at the end of each day!

This is a perfect holiday for those with only a basic fitness level.

DAY 1: Arrive

Starting Point: Chiusi

We recommend flying to Rome, Florence or Pisa and then catch the train to Chiusi (Train 1h30, 2h30 and 1h50 respectively). Our representative will meet you for a short briefing and transfer you to your hotel in Montepulciano.

Overnight: Hotel Albergo Il Marzocco

The Hotel Il Marzocco has been operating as a hotel since 1860 and by the same family since 1900. It has the welcoming and refined atmosphere of a large country house and is furnished with genuine XIX century furniture.


Montepulciano to Pienza—5 Hours

Starting from the San Biagio church you follow a quiet dirt road to the charming village of Montichiello where you can pause for a relaxed lunch or perhaps just a quick cappuccino before continuing to Pienza. Pienza is a UNESCO World Heritage site because of it’s unique renaissance architecture and town planning. Additionally it is well known for the production of pecorino cheese and truffles.

Overnight: Hotel Pienza San Gregorio

Hotel Residence Pienza San Gregorio offers a tranquil retreat just meters away from the ancient walled town. Large comfortable rooms, a lovely restaurant serving traditional Tuscan food and an outdoor swimming pool combine to make this a favorite stop.


Pienza to Bagno Vignoni—5 Hours

Today you wander through a beautiful region of rolling hills, oak woods, cypress trees and pretty villages. The thermal baths complex at Bagno Vignoni is the perfect location to spend the afternoon relaxing.

Overnight: Albergo Le Terme or (Country Hotel)

Depending on availability you will stay at Albergo Le Terme, which is in the centre of town and is surrounded by steam from the thermal springs or a lovely agriturismo 2 km outside town on the trail.


Bagno Vignoni to Sant’Antimo—6 Hours

A hard but enjoyable days walking, following dry riverbeds through a fairly wild environment brings you to St Antimo, an isolated abbey situated in a pastoral landscape. After exploring the Abbey we will transfer you to the Medieval town of Montalacino for the night.

Overnight: Hotel Dei Capitani

Hotel Dei Capitani is fantastically positioned in the centre of the Medieval town of Montalcini, offering wonderful panoramic views of the Tuscan Countryside, from the beautifully designed swimming pool and terrace. You will experience warm Tuscan hospitality during your stay here.


Montalcino to Buonconvento —7 Hours

A fairly long day, walking in the famous Brunello wine region, passing vineyards and olive groves, then again entering the beautiful Tuscan landscape of the “Crete” and Buonconvento, where you will stay in a lovely agriturismo.

Overnight: Fattoria Pieve A Salti

After a wonderful walk you reach Fattoria Pieve A Salti. A traditional Tuscan agriturismo (country hotel) with outdoor swimming pools and a rustic restaurant which serves delicious food grown on the estate.


Onward Travel

From Fattoria Pieve A Salti we will transfer you to Buonconvento rail station where you can catch the train to Siena and the airport, or perhaps your next destination in Italy.

Price per person for twin sharing basis. Single supplement add 160 EUR.

  • Accommodation: Handpicked small hotels, country inns and agroturism hotels.
  • Meals: A hearty breakfast included. Lunch and dinner not included but always available at accommodation or nearby.
  • Baggage Transfer: Door-to-door baggage transfer.
  • Travel: Taxi transfers as detailed in itinerary.


  • Personal briefing on arrival and support from our local representative if required.
  • 5 Nights accommodation including breakfast in rooms in hotels or agrotourism hotels.
  • Daily door to door baggage transfer.
  • A detailed info pack, route notes and map for your group leader.
  • Transfers as detailed in the itinerary.
  • Emergency telephone support from our office in the event of a problem.


  • Travel to the start (Chiusi) or from the finish (Buonconvento) of the walk.
  • Lunches, dinners, snacks and drinks.
  • Travel Insurance.
  • Personal Equipment.
  • Taxi transfers or public transport should you need to skip a stage.

Why Choose a Self Guided Walking Holiday in Tuscany?

Self guided walking holidays are a wonderful relaxed way to discover the landscapes, food and wine of Tuscany. Free to travel at your own pace and wander off the beaten track you will discover the beauty of the landscape, the warmth of the people and the long history of this spectacular land. We will supply you with comprehensive route notes, a clear map and a predeparture information pack to guide you every step of the way. Your baggage will be collected and moved onto your next accommodation so that you are free to walk each day with just a daypack. In the unlikely event you should require emergency support our office is always available.


Additional Nights

Many of our clients choose to add extra nights along the walk to sample more of the wonderful walking and attractions available in Tuscany. If you choose to extend your holiday we would recommend spending extra nights in Montepulciano or Pienza.

Extensions Why not extend your time in Italy with a few nights in Florence, Rome or even Venice? We offer several short city extensions and would be happy to tailor one to your needs.

Holiday Information


One of the highlights of this tour is the high standard of the accommodation. We specifically choose the hotels and agriturismo (country hotels) to ensure that you enjoy every minute of your stay. All offer a warm Tuscan welcome to walkers, traditional hospitality and delicious local food and drink.

Accommodation Details

We will always try and accommodate you at the locations detailed in the itinerary, but because of limited availability we may have to accommodate you at an alternative location of the same or better standard. Alternative details will be noted on your accommodation sheet.

Single Rooms

This independent walking holiday is not available to solo walkers. If you require single rooms in your party we will of course try to accommodate your request, subject to availability and payment of a single supplement.


The delicious Tuscan food and wine available locally is undoubtedly a highlight of this holiday. The price of your holiday includes a hearty breakfast each morning. Lunch and dinner are not included so you are free to choose from the available options. Most of your accommodations will more than happy to provide a packed lunch on request and this can be booked on arrival. Alternatively your route includes details of local shops and convenient lunch stops on the way. Dinner is available either at your accommodation or nearby restaurants.

Baggage Transfer

Your bags will be transferred from your accommodation as per your itinerary and moved onto your next overnight accommodation. We ask you to limit your luggage to one bag of up to 20kg per person.


Your information pack has a detailed equipment list which includes standard walking gear such as good walking boots or shoes, warm and waterproof clothes and a day pack.

Recommended Reading

Tuscany & Umbria—Lonely Planet Regional Guides Under The Tuscan Sun—Frances Mayes


Unfortunately we are unable to accommodate children younger than 14 on this walking holiday.

Payment terms

30% deposit to be paid on booking Remaining amount to be paid 8 weeks prior to departure.

Travel Information

Getting to Chiusi

We recommend you catch the train from Rome, Pisa or Florence to Chiusi. Trains run regularly and take 1h30, 2h30 or 1h50 respectively and cost approx 22 Euro from Pisa. Tickets can be booked on arrival or online prior to departure. Visit www.trenitalia.it for times, prices and booking. Parking at additional cost can be arranged in advance if you are driving.

Getting from Buonconvento

Trains run regularly from Buonconvento to Siena (25min) where you can change trains to reach the airport at Pisa (2h10, 8.90Euro) or Florence (1h30 6Euro).

Responsible Travel

Minimise Impact & Maximise Benefit

Our operating policies, office policies, holidays and tours are all designed to minimise impact and maximise benefit to the environment and local communities.

Action & Advocacy

We believe that by engaging our team and clients in environmental and community projects we can make a real difference.

Carbon & Communities

Travel and our business activity does of course contribute to carbon output and climate change. We have put several policies in place to minimise our carbon footprint.

"The accommodation was varied which made it exciting, All very clean and comfortable.Thoroughly enjoyed our time in Tuscany. Thanks Macs for your professional and thorough organizing." Rita P, Melbourne

"Getting out in the beautiful Tuscan countryside was wonderful, and this trip allowed us to visit several quite remote and charming towns without a car. The accomodations were superb, particularly in Montepulciano & Montalcino.As fairly experienced walkers we found the walks pretty tough. Temperatures were in the mid-30C range, and wall-to-wall sunshine so not surprising, but nevertheless the up-down-up-up steeply and down nature of the walks was more demanding than expected.The movement of our luggage was once again faultless." Ewan & Jenny, Dunblane

"Great holiday" sjandm, London

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