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Walk from the medieval powerhouse of Siena, across the UNESCO protected Val d’Orcia region, to the elegant hilltop town of Montepulciano. South of Siena follow sections of the ancient pilgrim’s path, via Francigena, deep into a landscape of soft rolling hills and avenues of towering cypress trees. Explore the 16th-century wine town of Montalcino, renowned for its precious Brunello wine and enjoy the Roman way of life, soaking in the hot springs of Bagno Vignoni.
Ramble through chestnut groves, vineyards and across classic Tuscan landscapes. Visit the hilltop hamlets of Castelnuovo dell’Abate and Monticchiello and if you’re lucky, you may hear the mesmerizing Gregorian chants at the Abbey of Sant’Antimo. Finishing off with 2 nights in Montepulciano allows ample time to explore the charming streets and Renaissance architecture of Montepulciano.
During this tour, you will spend each night in small family-run boutique B&B’s and 3* and 4* hotels. Chosen for their location, facilities and history, each accommodation is used to welcoming walkers. Of course, you can always call us too should you need anything during your walk. As many of the overnight stays are in small villages or towns, on occasion we may have to book another similar accommodation of equal standard. We will discuss these options with you during the booking process.
You will be provided with 7 breakfasts and 1 dinner. Lunches are available at various cafes or food stores daily. There are numerous places to get dinner each night, your hosts will give you a list of recommendations. If you have any food allergies or intolerances, please let us know at the time of booking so we can let your hosts know. Should you have severe food allergies, it’s always worth bringing a few of your own snacks with you.
We grade this trip as moderate. Tracks and trails may have short steep hill sections, some rough surfaces and steps. A moderate active lifestyle makes walking more enjoyable, an exercise regime of 2 to 3 times a week is needed. Walks are generally along well-defined trails. You should be used to walking between 10km-19km per day with up to 500m of ascent and descent. The vast majority of trails and tracks are well defined and cover a variety of terrain. On any typical day, you will be walking on forest trails, gravel tracks, rolling farmland, through vineyards and into the villages and towns where you will stay. It is commonplace in Italy that there are no separate footpaths (even in the towns) which means you will often be walking on the road. Please always be mindful of all road users when doing so. For each of the walks, you will be provided with daily walk notes, a map and the GPX tracks if you require to use them for your own device.
This walk is available from late April to the end of June and mid-August through to October.
Not available from 1st July – 22nd August.
From April into May the days are warm and sunny with equally pleasant evenings. Into June, sunflowers are in full bloom, vineyards are flowering, and the days become much warmer (up to 30 degrees). Village piazza’s buzz with life and are perfect for enjoying an al fresco dinner. Mid-August into September marks the beginning of the grape harvests, so you might be lucky enough to encounter a local festival or two. By October, the summer heat has retreated. The days are warm with evenings cooling off. It isn’t uncommon for Tuscany to experience thunderstorms during summer days, so you should always be prepared for a change of season during the day.
This walk starts in Siena and ends in Montepulciano. There is no airport in Siena. However, you can drive or take a train or bus to Siena from other airports near Siena. Florence and Perugia are the closest airports to Siena and the larger airports of Pisa, Bologna and Rome generally offer a wider range of routes across Europe and beyond. Leaving Montepulciano is very easy to venture by train. Always remember to stamp your ticket before travel on either buses or trains!
Florence airport
You can travel by bus from Florence airport to Florence central. The bus service terminates in central Florence beside the main railway station of Santa Maria Novella. The journey is approximately 25mins. You can then choose to go to Siena by bus or by train. By bus the journey time is 1hr – 1hr 30mins. There are two different bus lines that run between Florence and Siena. The RAPIDA or 131R is the fastest. It goes directly between the two cities on a dual carriageway. The DIRETTA stops at Poggibonsi and in Colle val D’Elsa – and can be handy if you would like to stop off and explore. By train the journey time via Empoli is 1hr 30mins.
Pisa Airport
From Pisa Airport you can take the ‘Pisa Mover’ train shuttle to the Pisa Centrale station to change for direct services to Siena. Journey time is 1hr-40mins. Please note You cannot buy tickets for the Pisa Mover in the main railway station. You have to walk down to the Pisa Mover itself where there are separate train ticket machines.
Rome Airport
Rome has two airports. Fiumicino and Ciampino. Whether you are travelling from Ciampino or From Fiumicino airports the best option is to head north and change at Chiusi-Chianciano Terme. From Ciampino Airport to Chiusi-Chianciano the journey is between 2hr 32min – 2hr 55 mins. From Flumicino Airport to Chiusi-Chianciano the journey is between 2hr 44min -3hr 55mins. From Chiusi-Chianciano the journey to Siena is 1hr 27min.
The other option is to take the fast train from Rome to Florence. Journey time is 1hr 36m and then connect with the train or bus for the next section of the trip.
Perugia Airport
From Perugia airport you can get a bus to Perugia Train Station. From here there are a few options. Firstly, you can take a bus. SAIS Autolinee have a bus service that takes around an 1 hr 30 mins. Secondly, you can go by train to Terontola, change and head for Chiusi, change again and go to Siena. Finally, you can choose to travel by train to Arezzo. The trip should take around 1hr. From Arezzo there is a bus service to Siena that will take around 1hr 20 mins.
Bologna Airport
From Bologna airport you can get a shuttle into Bologna’s Central Train Station and then a train to Florence. The Shuttle will take around 30 mins and the train to Florence will also take around 30 mins. From Florence you can choose to take the train or bus, as detailed above.
From Montepulciano, you can catch a train from two nearby stations. The closest but smallest station with less services is Montepulciano Stazione (9km away, approx. 10 mins by car or 20 mins by bus). The other is Chiusi Chianterme Station (24km away, approx. 30 mins by car or 50 mins by bus). This is a larger station offering more frequent bus services and supports another train service line from Siena.
For all train travel in Italy prices, timetables and ticket reservations can be made through Trainline or Trenitalia.
Another useful planning tool for travel is Rome2Rio should you be travelling from, or to, other destinations.
We require that you have adequate travel insurance against potential losses, damage or injury, including cancellation costs and loss of luggage.
For all trips that require international travel, you must have purchased travel insurance that also includes medical evacuation coverage.
We also charge a cancellation fee if you cancel your walking holiday after we have confirmed it to cover costs incurred from our suppliers and in the office. See the FAQ section for more information.
If you have any questions, feel free to ask one of our destination consultants. You can get in touch with us via our contact form or email us at info@Stroll.com
from $ 1190
Not available from 1st July – 22nd August
from $ 1040
Not available from 1st July – 22nd August
from $ 1080
Not available from 1st July – 22nd August
Walk from the medieval powerhouse of Siena, across the UNESCO protected Val d’Orcia region, to the elegant hilltop town of Montepulciano. South of Siena follow sections of the ancient pilgrim’s path, via Francigena, deep into a landscape of soft rolling hills and avenues of towering cypress trees. Explore the 16th-century wine town of Montalcino, renowned for its precious Brunello wine and enjoy the Roman way of life, soaking in the hot springs of Bagno Vignoni.
Ramble through chestnut groves, vineyards and across classic Tuscan landscapes. Visit the hilltop hamlets of Castelnuovo dell’Abate and Monticchiello and if you’re lucky, you may hear the mesmerizing Gregorian chants at the Abbey of Sant’Antimo. Finishing off with 2 nights in Montepulciano allows ample time to explore the charming streets and Renaissance architecture of Montepulciano.
During this tour, you will spend each night in small family-run boutique B&B’s and 3* and 4* hotels. Chosen for their location, facilities and history, each accommodation is used to welcoming walkers. Of course, you can always call us too should you need anything during your walk. As many of the overnight stays are in small villages or towns, on occasion we may have to book another similar accommodation of equal standard. We will discuss these options with you during the booking process.
You will be provided with 7 breakfasts and 1 dinner. Lunches are available at various cafes or food stores daily. There are numerous places to get dinner each night, your hosts will give you a list of recommendations. If you have any food allergies or intolerances, please let us know at the time of booking so we can let your hosts know. Should you have severe food allergies, it’s always worth bringing a few of your own snacks with you.
We grade this trip as moderate. Tracks and trails may have short steep hill sections, some rough surfaces and steps. A moderate active lifestyle makes walking more enjoyable, an exercise regime of 2 to 3 times a week is needed. Walks are generally along well-defined trails. You should be used to walking between 10km-19km per day with up to 500m of ascent and descent. The vast majority of trails and tracks are well defined and cover a variety of terrain. On any typical day, you will be walking on forest trails, gravel tracks, rolling farmland, through vineyards and into the villages and towns where you will stay. It is commonplace in Italy that there are no separate footpaths (even in the towns) which means you will often be walking on the road. Please always be mindful of all road users when doing so. For each of the walks, you will be provided with daily walk notes, a map and the GPX tracks if you require to use them for your own device.
This walk is available from late April to the end of June and mid-August through to October.
Not available from 1st July – 22nd August.
From April into May the days are warm and sunny with equally pleasant evenings. Into June, sunflowers are in full bloom, vineyards are flowering, and the days become much warmer (up to 30 degrees). Village piazza’s buzz with life and are perfect for enjoying an al fresco dinner. Mid-August into September marks the beginning of the grape harvests, so you might be lucky enough to encounter a local festival or two. By October, the summer heat has retreated. The days are warm with evenings cooling off. It isn’t uncommon for Tuscany to experience thunderstorms during summer days, so you should always be prepared for a change of season during the day.
This walk starts in Siena and ends in Montepulciano. There is no airport in Siena. However, you can drive or take a train or bus to Siena from other airports near Siena. Florence and Perugia are the closest airports to Siena and the larger airports of Pisa, Bologna and Rome generally offer a wider range of routes across Europe and beyond. Leaving Montepulciano is very easy to venture by train. Always remember to stamp your ticket before travel on either buses or trains!
Florence airport
You can travel by bus from Florence airport to Florence central. The bus service terminates in central Florence beside the main railway station of Santa Maria Novella. The journey is approximately 25mins. You can then choose to go to Siena by bus or by train. By bus the journey time is 1hr – 1hr 30mins. There are two different bus lines that run between Florence and Siena. The RAPIDA or 131R is the fastest. It goes directly between the two cities on a dual carriageway. The DIRETTA stops at Poggibonsi and in Colle val D’Elsa – and can be handy if you would like to stop off and explore. By train the journey time via Empoli is 1hr 30mins.
Pisa Airport
From Pisa Airport you can take the ‘Pisa Mover’ train shuttle to the Pisa Centrale station to change for direct services to Siena. Journey time is 1hr-40mins. Please note You cannot buy tickets for the Pisa Mover in the main railway station. You have to walk down to the Pisa Mover itself where there are separate train ticket machines.
Rome Airport
Rome has two airports. Fiumicino and Ciampino. Whether you are travelling from Ciampino or From Fiumicino airports the best option is to head north and change at Chiusi-Chianciano Terme. From Ciampino Airport to Chiusi-Chianciano the journey is between 2hr 32min – 2hr 55 mins. From Flumicino Airport to Chiusi-Chianciano the journey is between 2hr 44min -3hr 55mins. From Chiusi-Chianciano the journey to Siena is 1hr 27min.
The other option is to take the fast train from Rome to Florence. Journey time is 1hr 36m and then connect with the train or bus for the next section of the trip.
Perugia Airport
From Perugia airport you can get a bus to Perugia Train Station. From here there are a few options. Firstly, you can take a bus. SAIS Autolinee have a bus service that takes around an 1 hr 30 mins. Secondly, you can go by train to Terontola, change and head for Chiusi, change again and go to Siena. Finally, you can choose to travel by train to Arezzo. The trip should take around 1hr. From Arezzo there is a bus service to Siena that will take around 1hr 20 mins.
Bologna Airport
From Bologna airport you can get a shuttle into Bologna’s Central Train Station and then a train to Florence. The Shuttle will take around 30 mins and the train to Florence will also take around 30 mins. From Florence you can choose to take the train or bus, as detailed above.
From Montepulciano, you can catch a train from two nearby stations. The closest but smallest station with less services is Montepulciano Stazione (9km away, approx. 10 mins by car or 20 mins by bus). The other is Chiusi Chianterme Station (24km away, approx. 30 mins by car or 50 mins by bus). This is a larger station offering more frequent bus services and supports another train service line from Siena.
For all train travel in Italy prices, timetables and ticket reservations can be made through Trainline or Trenitalia.
Another useful planning tool for travel is Rome2Rio should you be travelling from, or to, other destinations.
We require that you have adequate travel insurance against potential losses, damage or injury, including cancellation costs and loss of luggage.
For all trips that require international travel, you must have purchased travel insurance that also includes medical evacuation coverage.
We also charge a cancellation fee if you cancel your walking holiday after we have confirmed it to cover costs incurred from our suppliers and in the office. See the FAQ section for more information.
If you have any questions, feel free to ask one of our destination consultants. You can get in touch with us via our contact form or email us at info@Stroll.com
Not available from 1st July – 22nd August
Not available from 1st July – 22nd August
Not available from 1st July – 22nd August
Q: What happens if I don’t want to walk one of the days?
As some of the walks on this itinerary are loop walks you can relax in the grounds of your accommodation (some of which have a pool) or explore the local town and its wineries. On the days where you will be walking to the next town, it might be possible to travel with the taxi service which transports your luggage. You can also use the local bus service between towns. Your accommodation hosts will have up to date information and advice should you wish to travel to the next destination by local transport. There is always plenty of information about options for the day in your daily walk notes and as always, you can call us at the office for help during your walk should you need any assistance.
Q: Where would you suggest adding an extra night?
SIENA - An incredibly well-preserved city with the show stopping Piazza del Campo at the heart of Sienese life. It is also possible to take a short bus journey to the hilltop towers of San Gimignano (an hour journey, or private transfers can be quoted and arranged).
Q: Can you extend our stay in Montepulciano?
Of course, please let us know at the time of booking if you would like to extend your time in Montepulciano. There is so much to see, we’d suggest at least 1 extra night.
Q: Can my children walk with me?
We don't allow under 16's to do this walk. No discounts can be offered for children who do book.
Q: We’re travelling as friends, can we get a triple room?
Triple rooms can be difficult to book. Many accommodations don’t always offer them but we can offer a twin/double together with a single room.
Q: Can we reduce the days walked?
You can start this tour by taking the train on day 1 direct from Siena to Buonconvento or Montalcino. This would reduce the trip to 7 or 6 days. Alternatively, we can discuss booking an additional taxi transfer for you to omit any 1 of the walks.
Q: Can we extend the days walked?
Of course, you may want to start by looking at our Tuscan Explorer which is 10 days and 9 nights, starting in Florence and ending in southern wine town of Montepulciano.