Self Guided Walking Holidays & Cycling Holidays

Please wait …

Hill Towns of Tuscany Self Guided Walking Holiday


  • Southern Tuscany’s Val d’Orcia; Montepulciano, Pienza, Montalcino, Siena.
  • Walks between Renaissance and medieval towns, vineyards and olive groves.
  • The thermal baths at Bagno Vignoni.
  • Sant’ Antimo Abbey; serenity and the sound of monastic chants.
  • Enjoying excellent local wine; Brunello di Montalcino, Nobile di Montepulciano.

Walk between Renaissance and medieval hill-top towns of southern Tuscany, discovering Montepulciano, Pienza, Bagno Vignoni, Montalcino, and finally Siena. Your journey winds through a unique linear, almost geometric landscape of hills, vineyards and olive trees.

Highlights include the spa baths at Bagno Vignoni and former Benedictine monastery at Sant’ Antimo Abbey. You’ll follow rewarding trails through the lesser known wine regions south of Siena. Take your time, slow down and discover the tastes and textures of Tuscany, one of Italy’s most beautiful and historic regions.

Day 1: Arrive Montepulciano

Your Tuscan walking tour begins in the medieval and Renaissance hill town of Montepulciano.

Montepulciano is easily accessible via Rome, Florence or Pisa; catch the train to Chiusi then take a local bus or short taxi ride to Montepulciano. Admire the impressive views over the rolling Tuscan landscape that you’ll be exploring over the next week.

Overnight: Montepulciano

Day 2: Walk to Pienza

Starting from the San Biagio church you follow a quiet track to the peaceful village of Montichiello where you can pause for a relaxed lunch or perhaps just a quick cappuccino before continuing on to Pienza.

Pienza is a UNESCO World Heritage site with unique Renaissance architecture. The town is well known for its delicious pecorino cheese and truffles; this is a great spot to indulge in Tuscan treats! Your tranquil hotel has an outdoor pool, and is just steps from the ancient walled town.  

Walk: 15 km

Overnight: Pienza

Day 3: Walk to Bagno Vignoni Thermal Baths

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 soaking up the Tuscan warmth.

Walk: 16 km

Overnight: Bagno Vignoni

Day 4: Walk to Sant’ Antimo, transfer to Montalcino

A more challenging but rewarding day’s walking awaits as you follow dry riverbeds through a fairly wild environment to Sant’ Antimo, an isolated abbey situated in a pastoral landscape. After exploring the abbey transfer to the medieval town of Montalcino.

Walk: 14 km

Overnight: Montalcino

Day 5: Walk through the 'Crete Senesi' to Buonconvento

A hearty breakfast will set you up for a long but enjoyable day of walking in the famous Brunello wine region, passing vineyards and olive groves, then again entering the beautiful Tuscan landscape of the “Crete Senesi” and Buonconvento, where you will stay in a lovely agriturismo (country hotel) with an outdoor pool; the restaurant serves food grown on the estate.

Walk: 17 km

Overnight: Buonconvento

Day 6: Loop Walk to Monte Oliveto Maggiore Monastery

A short day which is full of ups and downs, beginning with a transfer to the monastery at Monte Oliveto Maggiore, an impressive abbey built of red brick and set in the rugged Tuscan landscape.  

After an early visit to avoids the crowds, walk back to Buonconvento, perhaps stopping for a freshly made panini en route.

Walk: 11 km

Overnight: Buonconvento

Day 7: Transfer to Grancia di Cuna Medieval Farm, walk to Siena

Today you will start with a short transfer from to well-preserved medieval farm at Grancia di Cuna to start your walk to Siena.

Hike through a landscape of rolling hills and small hamlets as the unmistakable sight of Siena appears in the distance.

Enter the town through Porto Romana, one of the medieval gates, and walk though the city to reach your hotel.

Walk: 17 km

Overnight: Siena

Day 8: Onward travel

From Siena you can catch the train to the airport or perhaps continue your journey further within Italy; Tuscany combines perfectly with our coastal walks of the Cinque Terre or Amalfi Coast.


7 nights accommodation is included in your trip; stay in lovely 3 star hotels and country inns (agriturismo).  We carefully select small and friendly accommodation that offers great value, food and welcomes, so you enjoy every minute of your stay. Many of our walkers 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 Pienza, Montalcino or Siena.

Accommodation Details

We will always try and accommodate you at the locations detailed below, but because of limited availability we may have to accommodate you at an alternative location of the same or better standard.

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.

Additional Nights

Many of our clients choose to add extra nights along the walk or at the start/end of the walk. These can be added at the time of booking.




B&B l'Agnolo - Montepulciano

Located in the heart of Montepulciano. This once grand home is now a beautiful small and comfortable Bed and Breakfast, still displaying the ornate high fresco ceilings and wonderful surroundings. Expect a warm welcome during your stay in this unique bed and breakfast.







Hotel Marzocco - Montepulciano

The Hotel Il Marzocco has been operating as a hotel since 1860 and operated 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.







Residence San Gregorio - Pienza

Residence San Gregorio is situated a few hundred meters away from the ancient walled town of Pienza, in the heart of Tuscany. The Hotel Residence San Gregorio is an ideal exclusive environment to spend a night or a few days immersed in the magical atmosphere of a renaissance town, considered to be an architectural jewel.







Hotel Le Terme - Bagno Vignoni

Surrounded by the warm steam from the thermal spring, continuing the legend of healthy water, one finds the ancient construction of the Rossellino, home of Pope Pius II Piccolomini, today known as the Hotel "Le Terme". The rooms are decorated in classical style and the restaurant specialises in traditional Tuscan style food where simple ingredients are combined into delicious dishes. All complimented by delicious wines from the surrounding villages.







Hotel Dei Capitani - Montalcino

Hotel Dei Capitani is fantastically positioned in the centre of the Medieval town of Montalcino. You will delight in the wonderful panormaic views over the Tuscan countryside, from the beautifully designed swimming pool and terrace area. You can expect a warm welcome during your stay in this charming Hotel.







 Fattoria Pieve a Salti - Buonconvento

Fattoria Pieve a Salti - Buonconvento

A traditional Tuscan agriturismo, offering total tranquility and overlooking the incredibly beautiful Tuscan countryside. Enjoy the vast array of facilities on offer, with outdoor swimming pool, spa, horseriding and the rustic restaurant which serves excellent home grown food from the estate.







Hotel Chiusarelli - Siena

The building is a Neoclassical villa which was built around the 1860s and became one of the first hotels in Siena. In 2010, it was completely restored, maintaining its original style. In the magnificent frescoed halls, guests feel like they have gone back in time. Hotel Chiusarelli adds a gastronomic note to your stay in Siena with its Restaurant “Gli Orti di San Domenico”, where you can dine in a charming atmosphere, tasting typical recipes and dishes from traditional Tuscan cuisine.





The Hill Towns of Tuscany is available from March to November. Although you can walk in July and August if you want it is not recommended as it can get very hot. 

Single Rooms & Solo Walkers

If you require single rooms within your party we would be happy to accommodate you although there is a single room supplement payable. Should you be a solo walker wishing to book this tour, then a solo walker supplement is payable, as some costs are not shared.


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.

Maps, Route Notes & Navigation

The routes are waymarked in some areas, but not in others. However we provide you with detailed turn-by-turn route notes and maps and you will also have access to the Macs Adventure Smartphone App enabling you to follow the route using your phone's GPS so you will have no problems finding the way.

Experience & Fitness

This trip is graded ‘easy to moderate’ overall, however it should be noted that the terrain is hilly and summer temperatures can be high. Most of the route follows dirt tracks and trails, and you will be following minor roads only occasionally. On days 4 & 5 the walking is graded more towards the ‘moderate’ side as these are more challenging days.

Baggage Transfer

Your bags will be collected from your accommodation each day and moved onto your overnight accommodation. We ask you to limit your luggage to one bag of up to 20kg per person.

Travel Insurance

It is a requirement of booking this tour with Macs Adventure that you have suitable travel insurance which covers you for the activity and emergency evacuation and hospital care.

General Information

The distances and ascent/descents are approximations of the recommended routes. Please be prepared by packing all necessary items, for example, proper rain gear (jacket and pants), sun hat, sunscreen. Your information pack has a detailed equipment list which includes standard walking gear such as good walking boots or shoes, warm and waterproof clothes for the cooler months and lightweight clothing for summer, and a day pack.

Getting to Montepulciano

By Air: We recommend flying to Pisa, Florence or Rome, and then you can catch the train from the city centre railway station to Montepulciano (usually changing in Chiusi or elsewhere). Approx. journey times to Montepulciano; Pisa 2h50-3h20, Florence 1h50-2h15, Rome 1h50-3h15). Train timetables are available at Trenitalia;

If you wish, from Chiusi you can opt to take a local bus, or taxi the short distance to Montepulicano (25 mins, payable locally).

Getting from Siena

From Siena, you can take the train back to Pisa )2h00-3h15), Florence (2h15-3h15) or Rome (2h15-3h20). Again, please see Trenitalia's website for timetable planning.





  • 7 Nights in small hotels and country inns (3-star standard).
  • 7 Breakfasts.
  • Daily baggage transfers between hotels.
  • Taxi transfers as per itinerary (days 4, 6 & 7).
  • Information Pack, maps, route notes, GPX tracks, access to our smartphone app
  • Emergency telephone support from our local partner and UK office.


  • Travel insurance (required).
  • Travel to Montepulciano and from Siena.
  • Lunches, dinners, drinks and snacks.
  • Taxi transfers or public transport should you need to skip a stage.
  • Personal equipment


  • Single room or solo walker supplement if required.
  • Extra nights before, during or after your walk
  • Private airport transfers.

We are often asked the following questions and we hope that you will find the answers useful. Please do not hesitate to contact us if you have any other questions or for more advice from our team.

How fit do I need to be?

This walking trip is graded moderate and involves 3 - 7 hours of walking each day so you should enjoy an active lifestyle to get the most from your time in Tuscany. If you are unable to walk on any day you can use taxis or public transport to move onto the next night's accommodation. 

When is the best time of year?

Spring in Tuscany is sublime and April, May and June are absolutely lovely. Autumn is probably our favourite time of year as the landscape is made up of a gold and red pallet so September and October are unmissable. July and August can be very hot so you will have to start walking early to miss the heat of the day, although the towns and villages are buzzing, which is great. 

How far in advance do I need to book?

We suggest you book as soon as your plans are finalised Tuscany is extremely popular especially during July/August.

How do the baggage transfers work?

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.

What equipment do I need?

You will need good walking shoes/boots, comfortable walking clothes, waterproof jacket and trousers, a daypack and hats/gloves etc.

Which is the best airport?

Either Pisa, Florence or Rome are convenient and you can reach the start/end of the walk by train in an hour or two. 

What happens if I can’t walk a stage?

You can use public transport or local taxis to continue to your next overnight stop.

Every view was like a painting


Love the self guided trip in Tuscany. Didn't need a group as the It was so much fun to wander around these wonderful towns. So beautiful every view was like a renaissance painting.

Kate the sketcher

Toronto Canada


Beautiful Scenic Tuscany


We were ready for hiking trails and the trails we used were actually fine gravel roads that are rarely used by cars. We would see one or two cars a day (mid-April). We could hike side-by-side most of the way. Only on the leg between Pienza and Bagno Vignoni did we really need our hiking boots. We were amazed that the trails did not include switchbacks. Climbs could be quite steep so we took our time. Even so, we would leave the hotel by 9 and make it to our destinations by 3. The scenery was breathtaking and if we had been driving by in a car, I would have been dying to get out and take long walks. We hiked for 5 days but if we only had three, I would recommend the Montepulciano to Montalcino section. You will wear out the words Beautiful and Gorgeous. The hotels were spotlessly clean and modernized and staff were welcoming. A great plus was the app because we could be confused and just check the app and know that we were on the right path. Our Italian Via del Sole representative, Niccolo, was wonderfully dependable, only a text away.

Happy Hikers



A holiday that exceeded my expectations in every way


An all round very enjoyable holiday




Wonderful way to see Tuscany upclose


We loved this trip. We felt that we got to see and understand Tuscany in a way that we never would have if we were travelling by car, train or bus. Walking on the white roads is a great idea with so little traffic and the views are spectacular. The maps and instructions provided were really easy to follow. We can thoroughly recommend this walk!

Kaye and Ross

Brisbane, Australia


A great holiday from start to finish


Our first self-guided walking holiday, and a great experience. The arrangements are excellent with good accommodation that seems to offer something a bit special in each place. The walking is not demanding, and allows plenty time to take in the sights, the culture and the food and drink. The Tuscany landscape is beautiful and of a different character each day. The ancient hill towns are like stepping back in history.




Hill Towns of Tuscany


Brilliant holiday, the local reps very helpful, stunningly beautiful place some original accommodation, distances managable. For this time of year though (end July) start early to avoid the midday heat. Two mild complaints, 1) the last day directions had us going straight across the round about (after the stud farm) on the main road then up the extreamly busy main road, for .5 k to a left hand turn, where as 'the way' takes a left at the round about though an industrial estate and following the river, i.e. you don't need to cross the river or walk up an horrendous road. Also at the accommodation, they may have been a little more willing to leave some breakfast out for us, incase we wanted to make a very early start (like 05:30).




Viva italia!


Lovely rolling hills of vineyards, olive groves, orchards, and crops. Blue skies, green fields with poppies. Beautiful landscape! Agriturismo in Buonconvento was wonderful place. If you have an extra day....stay there and lounge by the pool, sit on their terrace and enjoy their fine restaurant. Amazing food, scenery, wine, and of course...gelato!!


alberta, canada


Great week of walking, food and wine


What a great week of walking between the hill towns of Tuscany. The directions were very easy to follow and were very detailed. Trust your first instincts and don't second guess the intentions of the instructions. All turns are clearly explained, especially in the countryside. We found navigating the villages the hardest as often street names were absent or covered by scaffolding but locals were very happy to help out when needed. A great mix of accommodation from B and B to agritourisimo. Breakfast was included at all places and the selection of food was more than we had expected and was delicious. The length of the daily walks wasn't too long each day but the Hills up and down over the course of the day made the walk a bit more challenging than we had expected. We benefitted greatly from the use of our walking poles. During wet weather this may have been more difficult. Even in early April this area was quite warm, I think unusually so this year. We had dressed in layers but within 1/2 hour every day were down to just t-shirts. Each village had great dinner options and after a long day of walking we enjoyed some amazing meals and wine. I'd highly recommend this tour for breathtaking scenery, quaint villages and excellent food.

Bell family



Staggering scenery


A really good recipe for a holiday - active but relaxing. Sometimes the maps did not match the directions which was confusing. The walks need to be walked each year and any alterations necessary made to the directions. Obvious landmarks were ignored when they might have made good key positional finders. We would have preferred to walk from point to point rather than taking shuttles, but understood the need for this. We preferred staying in hilltop towns rather than the rather isolated agriturismo accommodation - we liked exploring the beautiful towns. We were not very keen on the last day's walk into Siena, but understand that you can't change the nature of that particular walk! Hotels were OK, but beds not always very comfortable, and staff sometimes not very friendly. Breakfasts were variable, from very good to rather poor (stale croissants). Some bathrooms had definitely seen better days - cracked tiling and second rate showers. However, all in all it was a great holiday and we have some wonderful memories - especially walking into Pienza. What a fabulous place!




A great holiday, would recommend.


Fantastic holiday, great hotels and such helpful people from the Viadelsole group,made us feel welcome and safe knowing they were there at the end of the phone if we needed them. Some of the instructions on our route were a little complicated when some simple indication ie brick wall, group of cottages, large oak tree would have confirmed we were on the right track, but thanks for all the effort, will have to try another area soon.

Hilly hiker.

Lymington Hampshire


Hill Towns of Tuscany

4.5 41


Enquire Now

Get adventure news, trail guides, new trip updates and destination inspiration by signing up to receive our regular emails. We only send these by email, and we never pass data to third parties for marketing purposes. Please confirm if you are happy to receive this travel inspiration & advice into your email inbox.

Our full data & privacy policy

Book self-guided walking holidays and cycling holidays with Macs Adventure. Explore Europe, the UK and the rest of the world and find out why thousands of people trust us to arrange their perfect self-guided adventure.

Get In Touch

lf you require more information before booking, please contact us on

+44 (0)141 530 5464

+1 -844-858-0740


© 2019

Macs Adventure - Head Office: Skypark 5, 45 Finnieston Street, Glasgow, G3 8JU, UK