Self Guided Walking Holidays & Cycling Holidays

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Hill Towns of Tuscany Highlights Self Guided Walking Holiday


  • Hills, vineyards & olive groves of Tuscany; Montepulciano, Pienza, Montalcino
  • Walks between Renaissance and medieval hill towns
  • The thermal baths at Bagno Vignoni
  • Sant’ Antimo Abbey; serenity and the sound of monastic chants
  • Great Italian food and wine— Brunello di Montalcino, Nobile di Montepulciano

This highlights tour showcases Renaissance and medieval towns nestled amongst the hills of south Tuscany. Walk from Montepulciano to Pienza, visit Sant’ Antimo Abbey and the baths at Bagno Vignoni. Then it’s on to Montalcino before finishing in the ‘Crete Senesi’ area around Buonconvento.

Slowly make your way on foot through these tranquil wine regions and escape the pace of 21st century life whilst discovering the highlights of southern Tuscany’s architecturally and historically fascinating towns and monasteries.

Day 1: Arrive Montepulciano

Your Tuscan highlights 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 four days.

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: 14km

Overnight: Montalcino

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

A hearty breakfast will set you up for a long but enjoy 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: Onward travel

Take a transfer to Buonconvento train station, where you can catch the train to Siena and then continue your journey on to your chosen airport. Alternatively, perhaps continue your travels further within Italy; Tuscany combines perfectly with our coastal walks of the Cinque Terre or Amalfi Coast.


5 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 adding time in 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 available to solo walkers and a supplement is payable, as some of the costs are not shared. 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.







Hotel Il Giglio - Montalcino

A charming retreat in the heart of Montalcino, a family-run Hotel in a warm and quiet building, facing a gorgeous landscape over the Tuscan countryside. This is “Il Giglio”. The hotel has just 12 rooms, each one with cast-iron bed frames, painted ceiling and travertine stone bathrooms in a harmonious blend of rustic Tuscan style and classical elegance. The breathtaking panorama through the windows contributes to create an atmosphere that can only be experienced, never described.







 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.





You can start this walking tour anytime between March and October. Tuscany is very popular so it’s best to book as far in advance as you are able to.  Please bear in mind that July and August can be very hot for walking.  

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 ideally need to start an walks early to miss the heat of the day, although the towns and villages are buzzing, which is great.

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.

Single Rooms & Solo Walkers

This trip is available to solo walkers and a supplement is payable as some of the costs are not shared. Should you wish to have single rooms in your party then again a single supplement is payable.  


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.


The route is not always waymarked but we supply detailed maps, route notes and access to the Macs Adventure Smartphone App so you will have no problem following the route.

Experience & Fitness

This trip is graded ‘easy to moderate’ overall, however it should be noted that although some of the daily walks are relatively short, 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.

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 Montepulciano (25 mins, payable locally).

Getting from Buonconvento

At the end of your trip, we transfer you to Buonconvento train station, where you can catch the train to 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.



  • 5 Nights in small hotels and country inns (3-star standard).
  • 5 Breakfasts.
  • Daily baggage transfers between hotels.
  • Taxi transfers as per itinerary (day 4 & 6).
  • 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 Buonconvento train station.
  • 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.
  • 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 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. 

How fit do I need to be?

This walking tour is graded easy to moderate and involves 3 - 7 hours of walking each day so you should enjoy an active lifestyle to get the most from your trip. 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 your walks 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.

What personal equipment do I need?

You will need good walking shoes/boots, comfortable walking clothes, waterproof jacket and trousers, a daypack and hats/gloves etc. Our comprehensive pre-departure information pack has a good kit list. 

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.

A rewarding experience in stunningly beautiful countryside


We had no idea just how stunningly beautiful the Walks in Tuscan Hills would prove to be. The hill top towns themselves were amazing and were welcome destinations after walks that gave us a real sense of achievement.






The walks were all wonderful. The first 2 days included walks through hill towns, which helped to break things up. The last 2 days were direct walks without scheduled breaks (except for the end destination). Special mention to the Day 2 walk: Pienza to Bagno Vignoni -- truly spectacular, like walking through a postcard. The upgraded hotel at Bagno Vignoni, the Relais Osteria Dell'Orcia, was a real gem, as was their restaurant. The last night's stay at the Agriturismo was a highlight, as was dinner at their restaurant. Niccolo was our contact for the duration of the tour. He was super attentive and responsive and always did his best to accommodate us. Thanks MACS and molto grazie Niccolo!


New York


Wonderful scenery, architecture, history, food and wine


We spent a very enjoyable 5 nights with MacAdventures in Southern Tuscany visiting wonderful hill towns that we would never normally visit. The scenery was stunning. The walks were well planned and the app made it easy to avoid getting lost even written descriptions a bit ambiguous or route conditions had changed. All 4 of the walks challenging, but 2 days particularly hard because so much uphill. We loved the historic hotels in Montepulciano, Montalcino and Bagno Vignone, but found the more modern hotels underwhelming.




Great time great value.


My overall impression of the tour is excellent. It was well planned and the accommodation were very good. We went end of September and it was very warm. I drank about a galllon of water each day. Bring good foot wear and the ability to take thousands of pictures. I would have extended in a couple of the towns for a day to rest. All of the places are different but amazing. The accommodations were great. Especially Le Terme. Wow that place was awesome. On the last day we ran into some unleashed dogs before we crossed the river. We walked into a vineyard to devert.




A perfect way to enjoy walking and wine!


I was very impressed with the organization of this trip. Everyone was on time - hotel checkins, transfers. The instructions were great but the app is brilliant for reassurance that one is going the right way. The views were breathtaking.

Il capitani



Recharge your batteries in Tuscany


Hiking in Tuscany in October was wonderful. Perfect temperature, lovely sunsets, beautiful days. Loved the trip, especially the stay in Montepulciano. The weakest lodging was the Agriturismo. They have two separate facilities about a mile apart. The pool and other activities were a mile away from the facility where we placed- it would be better to provide accommodations for hikers in the building where the activities are.


Rochester, NY


Said LOVED this walking tour!!!


I got up each day excited to do what was planned for me! When it ended, I wanted to do it all over again right away!




Just great!


Hugely impressed by the level of care and attention both pre and during our walk in Tuscany. Nothing was too much trouble - in Italy we were treated as one of the family.




40 perfect miles


a great way to see iconic Tuscan landscapes and explore wonderful hill towns south of Siena. well planned and varied walking routes with good friendly accommodation along the way. a very personal service from Macs Adventure local partners with advice on the routes and booking restaurants, organising transfers etc.




Spectacular Scenery, wonderful hotels.


Mac's service: The most important comment I can make would be whether or not Mac's Adventures delivers what it promises. My answer is a definite YES! I was somewhat hesitant to book a trip from a company I only knew about from their own web site, but I can attest that Mac's came through for me in a big way. The hotels were all very nice, and most were unique and memorable. Despite booking relatively late, each hotel gave us great rooms with wonderful views, and treated us in a way that let us know they valued Mac's business. Also, the baggage transfers came off without a hitch. Everyday I either left my bags in my room or the hotel lobby, set out on my walk, and without fail found my bags at my next hotel waiting for me (usually already in my room). Everyone I delt with from Mac's over the phone or in Italy was friendly and professional. The walks/hikes: Of course walking in Tuscany was beautiful. The scenery each day was magnificent. Over every hill a new scence unfolded and each seemed more lovely than the previous one. The towns were all a little different with their own personalities. I never tired of exploring them at the end of each day. Be prepared to eat and enjoy delicious meals each evening and occasionaly for lunch as well! While the walk was rated easy to moderate, I would consider it "easy AND moderate." These are not called HILL towns for no reason. There are streches of flat and downhill walking that are quite easy, but there are also extensive uphill climbs that are quite strenuous for someone of only average fitness (like myself). To fully enjoy this tour, please get in shape before arriving in Italy. "Trail Conditons": One thing that surprised me were the "trails/paths" we walked on. More than half the time we walked along small gravel roads. Traffic was usually light, but these were public roads and not paths. Our route varied widely from paved and gravel roads, to farm roads, to faint paths through fields. About half the time we had sweeping views of the surounding countryside as we walked. We only rarely had to walk on paved roads, but it is worth noting that on the final day our route took us down a major two lane paved highway for 1.7 km. The entire way a steady stream of traffic buzzed past us at speeds exceeding 50 to 60 miles per hour. This part of the hike was a little unsettling. Mac's walking directions: Of course one of main items you are paying for are the directions/instructions provided by Mac's adventures to get you from one place to the next. Overall these were very good.The route notes were very detailed and not only told you which way to go, but frequently told you which way NOT to go. I found this very helpful. You should be aware that as good as the route notes are, they are not perfect and you need to exercise good judgement. For example, the notes said to walk to the right of a certain restaurant. Well, a restaurant was there, but the name had changed. Once or twice the notes referred to a waymark on a telephone or electric pole. Well, some of the poles had been replaced and the waymark was not present. While walking through a field we encountered a fence blocking our path that was not mentioned in the notes. On the last day the instructions led us directly to our hotel for the night, the problem was that the name of the hotel in the notes did not match the actual name of the hotel. After 14 miles of walking we were relieved to discover the notes were mistaken and we were at the right place. Etc., Etc. These were not big problems, and we never got lost or felt significantly confused, but as you can see you must occasionally use some good judgement, continue on, and trust the route notes. Final note: Dogs! If you are afraid of dogs this might not be the trip for you. There are dogs everywhere in the Tuscan countryside. Most of these were of no consequence, but several times we came across groups of sheep dogs tending their flock. While I never felt in danger, these dogs like to bark, growl, surround, and intimidate anyone who gets too close to the sheep. Once the flock was directly on the trail and the dogs "forced" us to cut across the pasture going off trail to avoid a confrontation. The only truly frieghtening encounter was when we tried to visit a recommended abbey along the route. As we approached the abbey a large rottweiler charged at us and was very aggressive. We backed away slowly and it eventually left us alone. Needless to say, we did not see the abbey! This was a wonderful trip with my teenage son, and I recommend it wholeheartedly. Mac's did a great job in all facets of its service and Tuscanny is one of the most beautiful places on earth. I wish I was still there.

T. W.

Mississippi, U.S.A.


Hill Towns of Tuscany Highlights

4.7 15


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