Hill Towns of Tuscany Highlights6 Days & 5 Nights 4.8 Read 19 reviews
- Explore the famed hill towns of Southern Tuscany on foot
- Scenic walks between Renaissance and medieval towns, vineyards, and olive groves
- Relax and recharge in the thermal baths at Bagno Vignoni
- Time to reflect and listen to the sound of monastic chants in Sant’ Antimo Abbey
- Fantastic cheese, pasta, and wine including Brunello di Montalcino and Nobile di Montepulciano
Slower Adventures | Where walking and cycling meet easy-going exploring, our Slower Adventures are the perfect combination. Most days are filled with picturesque journeys with some free time to dive into the destination and experience the people, local food and culture as you go.
Inn to Inn Walking | Walk from place-to-place changing accommodations each night. Generally staying in B&B’s, inns, and guesthouses.
This trip is suitable for:
As a guide, we would suggest that the minimum age of traveler this tour would be suitable for is: 12 Years
Ideal if you have an interest in:
Activity Level & Terrain
Grade & Terrain
We have created this “signature” itinerary to showcase the best walks and to create the perfect balance of sightseeing and cultural experiences.
This tour is graded easy to moderate with 4 days of walking and a maximum distance of 11 miles. Daily walks average around 9 miles (6 hours) along rolling terrain as you walk to-and-from hilltop villages.
Most of the route follows farms tracks and dirt trails, while on some days you will be walking along minor country roads with minimal traffic. On the fourth and fifth day of this trip, the walking is a bit more challenging due to the rugged ups and downs of the Tuscan region south of Siena.
You should be in decent physical shape and comfortable walking every day to fully enjoy the walking on this tour.
The routes are waymarked in some areas, but not in others. However, we provide the Macs Adventure Smartphone App making it simple to follow the route using a smartphone. Rest assured that by downloading the route maps in our app, that this will continue to work even in areas without any mobile or internet reception. For extra reassurance there are turn-by-turn route notes within the app too for the majority of walks.
Stay in charming small hotels, guesthouses and agriturismos. We carefully select small and friendly accommodation that offers great value, so you enjoy every minute.
Many of our walkers choose to add extra nights along the walk to sample more of the wonderful walking and attractions available in Tuscany. We would recommend spending extra nights in Pienza, Montalcino and/or Siena. Please notify us at the time of booking should you wish to add extra nights.
Single Rooms & Solo Walkers
This trip is based on double occupancy (two people sharing a room with one bed). If separate rooms are required, then a single supplement is payable. If a twin room is needed (same room with two separate beds), please notify us at the time of booking so we can request this option. This trip is available to solo walkers.
The delicious Tuscan food and wine is undoubtedly a highlight of this holiday.
Breakfast is included each morning and normally consists of a traditional European style continental breakfast ranging from coffee, tea, yoghurt, granola, meat, cheese, and baked goods. In some cases, a hot dish (eggs, pancakes, etc.) will be served or offered á la carte.
Lunches and dinners are not included in this trip. We recommend finding cafés or restaurants located in the towns or along the walking route, or to purchase snacks and a picnic lunch to bring along on the walks from local supermarkets and markets. Alternatively, most accommodations will be happy to provide a packed lunch on request and this can be booked on arrival. Dinner is available either at your accommodation or nearby restaurants. Further details can be found within your information pack and the Macs Adventure Smartphone App.
- Accommodation in en suite rooms in charming hotels, guesthouses and agriturismos on a twin share basis
- Daily breakfasts
- Transfer as per your itinerary
- Door to door baggage transfers as per your itinerary
- Access to maps, GPX tracks and daily route information with the Macs Adventure smartphone navigation app
- All your trip documents including a detailed information pack provided digitally through your online Macs “My Account”
- Telephone support from our offices and local partner in the event of a problem
- Travel insurance (required) and personal equipment
- Lunches, dinners, drinks, and snacks
- Tourist taxes (charged locally at hotels)
- Travel to and from start and finish points
- Any additional transfers or public transport required to shorten the walks or skip a stage
- Additional nights before, during or after the tour
- Private transfers to the start and from the end points of the tour
- Room upgrades
When To Go
This tour is available to start anytime between April to October, and possibly March, but we will need to check for you that the hotels have opened for the season as several in Tuscany only open at Easter, so it depends when this falls and if they have decided to open sooner.
Peak Season Availability
As Tuscany is a very popular destination, we suggest booking as soon as possible to ensure availability for specific dates.
Time of Year
The springs months of April, May and June offer warm sunshine, fewer crowds, and pleasant walking conditions. May is when most wildflowers are coming into bloom. The autumn months of September and October are also a favourable time of year, boasting cooler weather and a striking landscape made up of autumnal colours. July and August are good months to go but can be very hot for walking and therefore aren’t best suited for everyone. You will have to start early to miss the heat of the day and carry a lot of water (additional weight) with you. Although the towns and villages are buzzing at this time of year which is great to see.
Getting to the Start
If landing at Florence Airport, there’s a shuttlebus into the centre of Florence (taking around 25 minutes). It stops beside the main railway station of Santa Maria Novella.
If arriving at Pisa from the airport take the PisaMover to the main train station (takes 5 minutes). Turn left when exiting arrivals and the PisaMover is at the end of the airport.
Rome has two airports. From Fiumicino Airport take a train to the central station Roma Termini (taking about 30 minutes). From Ciampino Airport there’s a bus to Roma Termini.
Montepulciano is on a minor rail line and the station is a few kilometres outside of town. We have included a transfer from the train station to the town centre. We need you to advise us as soon as possible after booking as to which train you will be arriving on in order for the transfer to be arranged accordingly.
Alternatively, if you’d rather not use the included transfer from Montepulciano Train Station then rather than getting off the train in Montepulciano there are buses that run from Chiusi Train Station to Montepulciano Bus Station or you can take a taxi. The journey is about 25 minutes. Please let us know if you don’t require the transfer.
Approx. journey times to Montepulciano are:
From Florence 1hr50 - 2hr15
From Rome 1hr50 - 3hr15
From Pisa 2hr50 - 3hr20
Train timetables are available at Trenitalia. Please note that not all buses run on a Sunday or they may have a reduced timetable.
A private transfer can be requested. Please let us know at the time of booking if you would like to add this option (additional costs apply).
Getting from the End
From the agriturismo a private transfer is included to Buonconvento Train Station, where there are trains to Siena. Alternatively, a transfer to Siena can be arranged for an additional charge. Please ask our Sales team for details.
From Siena take the train back to Florence, Rome, or Pisa. Once again it will be necessary to travel from the central stations in these cities back to the airports (see ‘Getting to the Start’ for further information about this). Please see Trenitalia’s website for timetables.
Approx. total journey times from Siena are:
To Florence 2hr15 - 3hr15
To Rome 2hr15 - 3hr20
To Pisa 2hr00 - 3hr15
Siena Train Station is in the valley below the city centre and there are escalators between the two or there are local buses.
To Florence Santa Maria Novella there is usually a direct train that goes via Empoli and takes around 1 hour 30.
To Roma Termini in Rome it’s normally necessary to change trains in Chiusi-Chianciano Terme.
To Pisa there is usually a direct train that goes via Empoli and takes around 1 hour 40.
One bag of up to 20kg per person will be transferred from each accommodation to the next.
At Macs Adventure, we work in partnership with many luggage transfer providers who set a limit on how many bags/suitcases they will transfer per person, and also the weight of the bag/suitcase. Your booking includes transfer of 1 bag per person. It is very important that you read the luggage information specific to your tour before departure. If you do not adhere to these limits, there is a great possibility that you will be charged locally both for extra bags or if they are too heavy. This limitation can be a challenge, especially as airlines generally have limits that are higher. However, our luggage providers have reasons for these limits (usually due to the Health and Safety of their employees), which we must respect.
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.
The tour 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.
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.
To get the most from this trip you should be in good physical shape and comfortable walking on undulating terrain with many ascents and descents. Please read the ‘Is it for me?’ section of the web page and the itinerary for further information in order to ensure this trip is the right fit for you.
As Tuscany is a very popular destination, we suggest you book as soon as your plans are finalised to ensure availability for specific dates especially in travelling during July/August.
You will need good walking shoes/boots, comfortable walking clothes, a day pack, and dependent on when you are travelling; waterproof jacket and trousers, and hats/gloves etc. Our information pack has a list of all equipment to bring on your trip.
You can use public transport or local taxis to continue to your next overnight stop.
ItineraryDay 1 Arrive in Montepulciano, transfer to the town centre
This Tuscan walking tour begins in the medieval and Renaissance hill town of Montepulciano. On arrival at Montepulciano Train Station there is an included transfer to the town centre which is a few kilometres away.
The historic centre of Montepulciano is a traffic free zone so it’s a pleasant place to explore on foot. Admire the impressive views over the rolling Tuscan landscape that this tour will further explore over the coming days. The town is packed with elegant Renaissance buildings, ancient churches, and charming squares to sample a glass of local wine in whilst watching the world go by.
Please let us know your arrival train time as soon as possible after booking so your arrival transfer can be booked accordingly.
Owner Cinzia Caroli offers a warm welcome to all guests coming to her extraordinary charming B&B. Rooms are museum-like, decorated with period Italian antiques and frescoed ceilings while on the other hand you will have just recently renovated bathrooms with modern fittings.
A 10-minute walk from the centre of Montepulciano, this 18th century property is decorated with antique furniture and classical décor in keeping with its historic charm, whilst having modern amenities like WiFi access and air conditioning. This small hotel has a bar and peaceful gardens.
Leave Montepulciano through one of the historic gates before heading out into the surrounding countryside. From the San Biagio Church, follow a quiet trail pass vineyards and olive groves to the peaceful village of Montichiello. Why not pause here for a relaxed lunch or perhaps just a quick cappuccino before continuing to the hilltop town of 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!
For anyone wanting to take an easier walk today it’s possible to transfer to Montichello and walk from here to Pienza.
Shorter walk from Montichiello: 6kms/4mi Ascent/Descent: 472m/522m
Walk from Montepulciano: 15kms/9mi Ascent/Descent: 472m/522m
Recently renovated the Hotel Corsignano is a newly certified a “Green” Hotel. This beautiful 4- star Hotel is beautifully furnished and extremely comfortable, set in the frame of Tuscany's most beautiful and unspoilt area, reaching from Pienza to the Orcia-Valley.
Hotel Residence San Gregorio is situated a few hundred meters away from the ancient walled town of Pienza, in the heart of Tuscany. It offers 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.
This small hotel is set in a quiet position, surrounded by a peaceful garden and yet just a few steps from the historic town centre. There is an outdoor swimming pool with sun loungers and deckchairs to relax on. In the warmer months breakfast is served outside on the terrace. There is a wellness centre with Turkish bath, sauna, and treatments available (additional costs apply). There is also a bar and breakfast room. The comfortable bedrooms are equipped with air conditioning.
This is a particularly great walk as most of the time it’s possible to see both where you've been and where you are aiming for. Setting out on the walk from Pienza; admire the views across the valley with its typical Tuscan scenery of cypress trees, rolling farmland, and olive groves. Along the way stop in San Quirico d'Orcia. A walled town with an elegant 12th century church and ornate gardens. It is a great place to spend some time exploring.
Pass through Vignoni with its iconic stone tower before arriving in the spa town of Bagno Vignoni. The thermal baths complex is the perfect location soak up the Tuscan warmth and relax after a day’s walking.
For anyone wanting to take an easier walk today it’s possible to transfer to San Quirico d'Orcia and walk from here to Bagno Vignoni.
Shorter walk from San Quirico d'Orcia: 5kms/3mi Ascent/Descent: 311m/488m
Walk from Pienza: 14kms/9mi Ascent/Descent: 311m/488m
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 Relais Osteria dell’Orcia occupies a finely restored 16th century horse and carriage station, located along the Via Francigena, in the vicinity of Bagno Vignoni, where, in centuries past, pilgrims from Northern Europe traveling to Rome regularly sought rest and refreshment.
In the late 1990’s, Hotel Osteria dell’Orcia Relais became the subject of an extensive restoration project, which successfully reinstated the building’s original charm and, at the same time, allowed for the careful integration of the latest in modern comforts and technology
Today’s Hotel Osteria dell’Orcia Relais is an intimate, four star establishment, providing quality guest accommodation in just 16 bedrooms, each of which is individually furnished in romantic Tuscan country style.
A more challenging but rewarding day’s walking awaits. Follow dry riverbeds through a fairly wild environment. The view initially is dominated by the castle on the hill, Ripa d'Orcia. Ascending into the medieval village of Castelnuovo dell'Abate. There are fine views from here down the valley with its iconic Tuscan scenery and vineyards galore. Reaching Sant’ Antimo, an isolated abbey situated in a pastoral landscape. This large abbey is an impressive example of Romanesque Cistercian architecture. The exterior facade has a menagerie of animals, and the interior frescoes are very intriguing. After time to explore the abbey, there is an included transfer to the accommodation in the charming medieval town of Montalcino.
Located in the medieval old town of Montalcino with magnificent views of the Tuscan Hills. With an emphasis on excellent service this charming small hotel is situated in part of the eighteenth-century “Catasto Leopoldino” in the historic centre of Montalcino. However, there is reason to believe that the building may have been used since the Middle Ages (owing to its location in the vicinity of Porta Burelli) as a shelter for the Sienese people fleeing from the Florentine army.
Walk through the famous Brunello wine region, passing vineyards and olive groves, before entering the Tuscan landscape of the “Crete Senesi” with its rolling hills and farmland, dotted with patches of woodland and quaint little villages. The walk finishes up at Fattoria Pieve a Salti Agriturismo near Buonconvento. Our characterful accommodation is the ideal spot to relax after a long walk, alternatively why not explore a bit more and visit nearby Buonconvento. This photogenic village is still nearly entirely surrounded by the ancient city walls with only a small section being destroyed in World War II. There’s also a pretty little church and two small museums here - Religious Art Museum of the Val d’Arbia and the Museum of Sharecropping.
Alternatively, there is an easier walking option today, which is slightly shorter and is a gentle downhill route into Buonconvento village. Spend some time exploring here before transferring to Fattoria Pieve a Salti.
Shorter walk to Buonconvento: 12kms/7mi Ascent/Descent: 43m/396m
Walk to Pieve a Salti: 16kms/10mi Ascent/Descent: 277m/522m
Please note that on the rare occasions that the Fattoria Pieve a Salti Agriturismo is fully booked the accommodation will instead be in a small hotel centrally located in Buonconvento. In which case it will be the shorter walking option used today.
Fattoria Pieve a Salti is an agriturismo that has been converted from restored farm ruins into a stunning country hotel complex including a swimming pool and health centre. The rooms are furnished in traditional rustic Tuscan farm style.
This small hotel is on Buonconvento's main street, so is ideally located for exploring on foot. Its comfortable bedrooms have been decorated in a clean, modern style but have also highlighted the building historical features. They have air conditioning and WiFi access.
Hotel Ghibellino is a modern 23 room three-star hotel in the centre of Buonconvento. It has an excellent reputation and the comfortable air-conditioned rooms are a relaxing haven.
A short transfer is included to Buonconvento Train Station, where there are trains to Siena. Alternatively, it’s possible to arrange a private transfer to Siena for an additional charge. Please ask our Sales team about this at the time of booking.
From Siena catch the train to Rome, Pisa or Florence airports or perhaps continue to journey further within Italy. Tuscany combines perfectly with our coastal walks of the Cinque Terre and Amalfi Coast or any of the Umbria trips.
The Macs Way
- Tried & Tested Adventures
- Book with Confidence
- Positive Impact
- Knowledgeable and helpful specialist trip planners
- Wide variety of tours to suit all interests and experience levels
- Start on any date that suits you
- Choose your ideal trip length and difficulty
- Range of accommodation comfort levels
- Choice of trip styles
- Choose your own travel companions
- Walk, cycle and explore at your own pace
- Make your own decisions
- Choose your own path
- Indulge your passions
- 15,000+ unbiased trip & service reviews
- Feefo Platinum Award 2022
- 25,000+ travelers trust us each year
- As featured in the Guardian, Times, Nat Geo Traveler
- Founder owned & operated since 2003
- 100+ passionate team members across the US, UK & Europe
- Carefully planned adventures
- Quality, hand-picked accommodations
- Seamless and reliable arrangements
- Comprehensive trip information & insider tips
- Detailed maps, route notes and mobile GPS app
- Helpful 24/7 support should you need it
- Travel responsibly
- Explore off the beaten track
- Support locally owned businesses
- Engage with local communities
- Minimize your impact
- Maximize the benefit of your travel
- Challenge yourself & grow