Hill Towns of Tuscany
- Explore the famed hill towns of Southern Tuscany on foot
- Hike through scenic views of Renaissance and medieval towns, vineyards, and olive groves
- Relax and recharge in the thermal baths at Bagno Vignoni
- Enjoy free time to reflect and listen to the sound of monastic chants in Sant’ Antimo Abbey
- Be sure to sample the region’s famous cuisine: delicious Pecorino cheese, truffles, and wine including Brunello di Montalcino and Nobile di Montepulciano
Gallery
Itinerary
Day 1 Arrive in Montepulciano, transfer to the town centerThis Tuscan hiking trip begins in the medieval and Renaissance hill town of Montepulciano. Upon arrival at the Montepulciano Train Station, there is an included transfer to your hotel in town, which is a few kilometres/miles away.
The historic center 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 trip 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 while watching the world go by.
Please let us know your train's arrival time into the Montepulciano Train Station as soon as possible after booking so we can book your included transfer to your hotel accordingly.
Our hosts offer a warm welcome to all guests to their extraordinarily charming B&B. Rooms are museum-like, decorated with period Italian antiques and frescoed ceilings while on the other hand there are 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. This small hotel has a bar and peaceful gardens. A buffet breakfast with local products is included daily and can be served in the garden.
Leave Montepulciano through one of the historic gates before heading out into the surrounding countryside. From the San Biagio Church, follow a quiet trail past 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 - a perfect spot to indulge in Tuscan treats!
For anyone wanting to take an easier hike today, it’s possible to schedule a transfer to Monticchiello (payable locally) and walk from here to Pienza.
The Corsignano is in Pienza and offers breathtaking views of the Orcia Valley. This family-run hotel offers a terrace with hot tub, and a typical Tuscan restaurant. This comfortable and homely hotel is located in the town centre, just off the main square. They have a focus on sustainability and have received green certification.
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, perfect for relaxing after a day of activity. 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).
This is a particularly great hike 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 hike from Pienza, admire views of Tuscan scenery with cypress trees, rolling farmland, and olive groves from across the valley. 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 to soak up the Tuscan warmth and relax after a day’s hiking.
For anyone wanting to take an easier hike today, it’s possible to schedule transfer to San Quirico d'Orcia (payable locally) and hike from there to Bagno Vignoni.
The unique location is what truly makes this hotel special. Surrounded by the warm steam from the thermal hot springs located just outside. The hotel has a spa where you can partake in the mineral rich thermal waters. There’s a Roman sauna and treatments are available (additional charges apply). The restaurant specialises in traditional Tuscan cuisine where simple ingredients are combined into delicious dishes.
Set in a restored 16th century horse and carriage station, this small hotel is located on the Via Francigena, where, in centuries past, pilgrims from Northern Europe travelling to Rome regularly sought rest and refreshment. The building has retained its original charm and, at the same time, has all modern comforts. There is a restaurant, bar, garden, outdoor swimming pool. Massage treatments are available (charges apply).
A transfer in the morning at 0900am takes you to the medieval village of Castelnuovo dell'Abate and the Sant’Antimo Abbey, an impressive example of Romanesque Cistercian architecture. You have time here to explore this isolated abbey situated in a pastoral landscape. The exterior facade has a menagerie of animals, and the interior frescoes are very intriguing. From here, hike to the charming medieval village of Montalcino passing olive groves with fine views down the valley with its iconic Tuscan scenery and vineyards galore.
Montalcino is a classic Tuscan hilltop village with a complete circle of fortified walls. It is famous for it’s Brunello red wine, and its 16th century buildings are gloriously set with isolated cypress trees.
Ascent/Descent: 395m/180m (1,296ft/591ft)
Located in the medieval town centre of Montalcino with magnificent views of the Tuscan hills, this charming small hotel is situated in part of the 18th century “Catasto Leopoldino”. Enjoy the hotel's restaurant, bar, terrace, and a large panoramic garden with an outdoor swimming pool.
Hike 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 hike finishes at Fattoria Pieve a Salti Agriturismo near Buonconvento. It's an the ideal spot to relax after a long hike, or perhaps choose to 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 - the Religious Art Museum of the Val d’Arbia and the Museum of Sharecropping.
Alternatively, there is an easier hiking option today, which is slightly shorter and a gentle downhill route into Buonconvento village. Spend some time exploring here before taking a transfer (payable locally) to Fattoria Pieve a Salti.
This agriturismo has been converted from farm buildings into a stunning country hotel including both an indoor and outdoor swimming pool, garden, spa with sauna, steam room and massages available (additional charges apply; advance bookings recommended). The agriturismo is in a natural truffle zone, so this is often on the restaurants menu along with local wines and organic produce grown on the farm.
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.
Hotel Ghibellino is a family-run property in the centre of Buonconvento. It has a large terrace on the third floor providing a great view over the historic village. Cakes, fresh fruit and cold meats are served as part of the buffet breakfast.
A short but hilly day begins with a quick transfer at 0900am to Monte Oliveto Maggiore Monastery, an impressive abbey built of red brick and set in the rugged Tuscan landscape. The huge complex's main attraction are the frescoes in the cloisters, which portray the life of St. Benedict. After an early visit to avoid the crowds, walk back to the agriturismo near Buonconvento, perhaps stopping for a freshly made panini en route. Part of the route goes through shaded woodland as it explores more of the rolling Crete Senesi landscape.
Ascent/Descent: 230m/315m (755ft/1,033ft)
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. There will be a transfer to return from the end point to the hotel at around 3pm.
Alternatively, for anyone not wishing to hike today you may wish to explore the charming village of Buonconvento or perhaps book a massage treatment at the Fattoria Pieve a Salti Agriturismo.
This agriturismo has been converted from farm buildings into a stunning country hotel including both an indoor and outdoor swimming pool, garden, spa with sauna, steam room and massages available (additional charges apply; advance bookings recommended). The agriturismo is in a natural truffle zone, so this is often on the restaurants menu along with local wines and organic produce grown on the farm.
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.
Hotel Ghibellino is a family-run property in the centre of Buonconvento. It has a large terrace on the third floor providing a great view over the historic village. Cakes, fresh fruit and cold meats are served as part of the buffet breakfast.
Today starts with a short transfer at 0900am to the well-preserved medieval fortified farm at Grancia di Cuna. It’s on the site of what was once a 12th century hospice and hospital for pilgrims on the Via Francigena. It’s worth taking the time to explore this historic site before beginning the hike to the UNESCO listed city of Siena.
Alternatively, it’s possible to take a transfer today (payable locally) to Colle di Malamerenda, which is closer to Siena. It’s an easier hiking option, which is both shorter and less hilly and will allow more time to explore Siena on arrival.
Hike through a landscape of rolling hills and small hamlets as the unmistakable sight of Siena appears in the distance. Walk past vineyards and olive groves along the way. Finishing at the main medieval gate to the city, the Porta Romana, makes for a fantastic photo opportunity. A memorable end to a great tour!
Alternatively today, you have the option to arrange a private transfer or grab a taxi (additional charges apply) to go directly to Siena and skip the hike, in favor of spending more time exploring this iconic city.
If time allows, we recommend adding an additional night in Siena, as this is an ideal location to relax in a café beside the main square or to explore the winding streets at a leisurely pace after completing this hiking trip.
Situated in Siena city centre, so perfect for exploring on foot. Built in around 1870 as a Neoclassical villa, it was restored in 2004, keeping its original style as well as its beautiful, frescoed common rooms. The hotel has a restaurant, bar, terrace, and small garden to relax in.
This 18th-century residence was transformed into a hotel with all modern comforts. It’s adjacent to Porta Romana gate into the historic city and just a few minutes' walk from Piazza del Campo. The comfortable bedrooms are decorated in a traditional Tuscan style. There is a large panoramic garden where a bar service is available. Upon request, a in bedroom massage service is available (additional charges apply; advance booking recommended).
Located inside Siena's historic walls, Hotel Athena offers an elegant Italian restaurant and a furnished terrace with views of the town and the surrounding valley. Internet is free. With air conditioning, rooms are spacious and elegantly furnished with warm colour schemes and tiled floors. Rooms on the upper floors offer beautiful views.
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 hikes of the Cinque Terre and Amalfi Coast or any of the Umbria trips.
This trip has a carbon score of 5kg per person per night, meaning it’s one of our best trips! For comparison, a carbon count of 5kg is equivalent to 1 Neapolitan margherita pizza. Here at Macs, we pride ourselves on being a responsible travel company and continue to adopt, develop and innovate ways to positively impact the environment. Find out more information about how we've carbon counted our trips.
Other Information
Is it for me?Perfect for anyone who hikes regularly and wants to explore at their own pace. There are plenty of places of historic interest to discover amidst picture-postcard scenery, coupled with comfortable and welcoming accommodation and mouth-watering food and wine. There are some considerable ascents/descents (up to 520m or 1,700ft) to the hill towns at the start and end of the walks due to the nature of the rolling Tuscan scenery. It’s best to do some practice hikes ahead of time, including stairs, ascents and descents like those you will experience on the trip while carrying your day bag. However, most hikes can be shortened, and there is an optional hike that can be sat skippedif a rest day is needed. If time allows, we suggest adding a day at the end of the trip in historic Siena to soak up the atmosphere and rejuvenate before continuing with onward travel.
Classic Routes | If you’re the active, outdoorsy type, who’s interested in taking on the great routes of the world or looking for a challenge, then our Classic Routes are for you. We’re talking the West Highland Way in Scotland, the world renown Tour Du Mont Blanc and Germany's Moselle Cycle Path, to name but a few!
Inn to Inn Walking | Walk from place-to-place changing accommodations each night. Generally staying in B&Bs, inns, and guesthouses.
Solo Travellers, Families with Teens
The minimum age for this tour is: 12 Years
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 along with minor roads occasionally. On days 2, 4 and 5 the hiking is graded ‘moderate’ as these are more challenging days. There are options to shorten the hikes most days by joining the luggage transfer to get closer to your destination. The hike on day 6 is optional.
Stay in charming small hotels, guesthouses and an agriturismo. We carefully select small and friendly accommodation that offers great value, so you enjoy every minute.
Meals
The delicious Tuscan food and wine is undoubtedly a highlight of this vacation.
Breakfast is included each morning and normally consists of a traditional European style continental breakfast ranging from coffee, tea, yogurt, 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 hiking route, or to purchase snacks and a picnic lunch from local markets to bring along on the hikes. 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.
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.
- 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 info with the Macs Adventure app
- All your trip documents including a detailed information pack provided digitally through your online Macs “My Account”
- We're here for you 24/7 if you need anything, just give us a call
- Travel insurance (recommended) 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
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 spring 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 favorable time of year, boasting cooler weather and a striking landscape made up of autumnal colors. July and August can be very hot for hiking and therefore aren’t 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.
This trip starts in Montepulciano and includes a transfer from the Montepulciano Train Station (which is located a few km/miles outside of town) to your hotel. To reach Montepulciano, we recommend flying into Rome Airports (FCO or CIA) or Florence (FLR), however, flights in and out of this airport are limited. You can also arrive at the Pisa Airport (PSA), but you'll want to take the train to Florence in order to make your way to Montepulciano.
If arriving in Florence: There’s a tram that departs approx. every 10min that will take you to Florence’s main railway station – the Santa Maria Novella (takes 20min). From there, there are trains to Montepulciano, usually changing onto a different train with a layover in Chiusi or Sinalunga. Total travel time from SMN train station to Montepulciano train station ranges between approx. 2H15 – 3H30, depending on train changeover time in the connecting city.
If arriving in Pisa: From the airport take the PisaMover that departs approx. every 10min to the Pisa Centrale Train Station (takes 5 minutes). After exiting Arrivals, follow the signs for the PisaMover, turning left and walking along the passageway to the little Pisamover station at the end of this passageway. You can either take the stairs up or go up to the platform with the elevator. Once upstairs you can buy a ticket from the machine. From Pisa Centrale Train Station, trains to Florence leave around every 30min, and the journey takes approx. 1H15. From there, you'll want to follow the instructions for traveling to Montepulciano from Florence.
If arriving in Rome (note Rome has two airports): From Rome Fiumicino Airport (FCO), take the Leonardo Express Train that’s located inside the airport and departs every 15min to the central train station Roma Termini (takes about 32min). From Ciampino Airport (CIA), there’s a bus to Roma Termini (takes about 40min). From Rome’s Roma Termini Train Station, there are trains to Montepulciano, usually changing onto a different train with a layover in Chiusi or Siena. Total travel time from Roma Termini train station to the Montepulciano train station ranges between approx. 2H15 – 3H30, depending on train changeover time in the connecting city. If you would prefer not to wait for the connecting train in Chiusi, we can arrange a car transfer to your hotel (additional costs apply). You also have the option to arrange a taxi on your own.
Please check the Trenitalia website for timetable planning. Please note that not all buses/trains run on a Sunday, or they may have a reduced timetable.
As soon as possible after booking your train ticket, notify Macs what time you will arrive at the Montepulciano Train Station so that we can arrange your included transfer accordingly.
Alternatively, if you’d rather not use the included transfer from Montepulciano Train Station, you may choose to instead take a taxi or the bus that runs from Chiusi Train Station to Montepulciano Bus Station. The journey is about 25 minutes and is payable locally. Please let us know if you don’t require the included transfer.
If you’d prefer to avoid public transport from the airport, 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). Once your trip is confirmed please share your flight information with us, including your arrival time, as soon as you have booked your flights, so that we have those details well in advance and we can arrange the transfer for you ahead of time.
It's easy to travel from Siena by train to the major airports of Florence, Pisa, and Rome.
The Siena Train Station and Bus Station are located in the valley below the city center. (about a 2km/1.25mi walk from the majority of accommodations we use). To make your way to the station you have a few options (each payable locally): 1) take the escalators 2) take a bus or 3) take a taxi.
Approx. total journey times from Siena are:
To Florence 2H15 – 3H15
- The train to Florence Santa Maria Novella station is usually a direct train that goes via Empoli and takes around 1H30. Some trains are direct whereas others go via Empoli.
To Rome 2H15 – 3H20
- To Roma Termini Train Station it’s normally necessary to change trains in Florence or Chiusi-Chianciano Terme and takes around 3H30.
To Pisa 2H00 – 3H15
- To Pisa’s Train Station there is usually a train that departs approx. every 30min that goes via Empoli and takes around 1H45.
Once again it will be necessary to travel from the central train stations in these cities back to the airports (see ‘Getting to the Start’ for further information about this).
Alternatively, we can arrange a taxi from Siena to your departure city or airport. Please let us know in advance if you wish to include this option for an additional fee.
Please check the Trenitalia website for timetable planning. There are also local buses that you can take for your onward travel and you can find the information here. Please note that not all buses/trains run on a Sunday, or they may have a reduced timetable.
One bag of up to 20kg/44lbs 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.
To get the most from this trip you should be in good physical shape and comfortable hiking on hilly terrain with many ascents and descents. Please read the ‘Is it for me?’ section of the web page and the itinerary for further info 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 finalized to ensure availability for specific dates especially when traveling late Spring through early Fall.
You will need good hiking shoes/boots, comfortable hiking clothes, a day pack, and depending on when you are travelling: waterproof jacket and pants, and hats/gloves, reusable water bottle, etc. You may also wish to bring hiking poles. Our Information Pack has a list of all equipment to bring on your trip.
No problem! You can use public transport or local taxis to reach your next overnight stop.
Many of our hikers choose to add extra nights along the trip to sample more of the wonderful hiking 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.
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