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SELF-GUIDED
6 DAYS
Moderate
Walk across a timeless region of Tuscany to the medieval hilltop towns of Volterra, San Gimignano and Monteriggioni. Follow ancient Etruscan trails and pilgrim routes through vineyards and olive groves ending in the majestic Piazza del Campo in Siena.
The walk begins deep in the heart of Tuscany at Volterra, one of the most ancient Etruscan settlements. Set atop a high plateau, explore its labyrinth of cobbled streets awash with Roman and medieval architecture. Head east across a rolling landscape peppered with sleepy hamlets as the impressive 14 medieval towers of San Gimignano come into view.
Continue on your journey to Siena along the pilgrim route, Via Francigena. As thousands of pilgrims would have before you, walk the classic white gravel roads stopping to explore the perfectly preserved 13th-century walled town of Monteriggioni. The final day of this Tuscan discovery ends in Siena’s lively Piazza del Campo, the perfect spot to kick back and relax with an Aperol Spritz.
Today arrive at leisure into the old town of Volterra. Built on a high plateau, Volterra was once a trading powerhouse and although the old town is only a third of its original size, it is a joy to explore. Wander through a maze of cobbled streets, crammed with gorgeously preserved Etruscan, Roman and mediev
Today arrive at leisure into the old town of Volterra. Built on a high plateau, Volterra was once a trading powerhouse and although the old town is only a third of its original size, it is a joy to explore. Wander through a maze of cobbled streets, crammed with gorgeously preserved Etruscan, Roman and medieval architecture. Later in the evening, you will dine at a nearby restaurant to your hotel.
Accommodation: Hotel Volterra Inn
Located within the 5th-century walls of historic Volterra, the hotel is classically yet simply designed. All the rooms have an en-suite and there is a hotel bar open in the evenings, where you can enjoy an Aperol Spritz.
The day starts with a private transfer to the trailhead near Podere Fontanelle. Follow rural trails through the woodland of Castelvecchio nature reserve and into the sleepy hamlet of San Donato, nestled in the classic picture-postcard landscape. Nearing San Gimignano you’ll begin to see its Manhattan-like skyline of medieval towers. One of the most visited villages in Italy, the UNESCO listed historic centre is incredibly well preserved and is a step back in time to when the aristocracy of the 12th and 13th centuries flaunted their wealth by constructing the most elaborate of towers.
Walk: 16km
Ascent: 250m
Descent: 530m
Meals included: Breakfast
Accommodation: Hotel la Cisterna
Overlooking the Piazza Cisterna, the property has been at the heart of San Gimignano for over 1000 years. Rooms have views of the cobbled square, buzzing with life, or looking out over the vineyards and rooftops of the countryside. Restaurants and bars are only a few steps away and as you’re here for 2 nights there is also an opportunity to visit Gelateria Dondoli, a previous winner of the world’s best gelato shop.
Immerse yourself in classic Tuscan countryside as you spend the day walking through the villages and vineyards east of San Gimignano. Follow the traditional white gravel roads (strade bianche) which are a defining feature of Tuscany. Pass through the historic settlements of Poggio Casaglia and Poggio Alloro where you can enjoy a picnic under the olive trees or have lunch in a traditional Fattoria. On return to San Gimignano, you’ll soon see the familiar towers before arriving into the bustle of the historic centre.
Walk: 16km
Ascent: 500m
Descent: 500m
Meals included: Breakfast
Accommodation: Hotel la Cisterna
Today follow the Via Francigena, an ancient pilgrim route starting in Canterbury, England and finishing in Rome which has been walked by pilgrims since the 6th century. Not long after leaving San Gimignano, you’ll be back enjoying the gorgeous Tuscan countryside, including vineyards, as you head south towards Colle Di Val D’Elsa. This is a beautiful amble through a Tuscan la
Today follow the Via Francigena, an ancient pilgrim route starting in Canterbury, England and finishing in Rome which has been walked by pilgrims since the 6th century. Not long after leaving San Gimignano, you’ll be back enjoying the gorgeous Tuscan countryside, including vineyards, as you head south towards Colle Di Val D’Elsa. This is a beautiful amble through a Tuscan landscape of olive groves and vineyards, the route descends into the new town and shortly after into the charming medieval centre and relaxed piazza.
Walk: 13.5km
Ascent: 280m
Descent: 430m
Meals included: Breakfast
Accommodation: B&B Arnolfo
Located next to Ponte di Campana, the Arnolfo is in the heart of the old town and within a few minutes stroll of the historic sights. Rooms have typical stone walls, timber ceilings and have an ensuite. If you wish to relax you can also take advantage of the guest reading room and small garden.
ndscape of olive groves and vineyards, the route descends into the new town and shortly after into the charming medieval centre and relaxed piazza.
Walk: 13.5km
Ascent: 280m
Descent: 430m
Meals included: Breakfast
Accommodation: B&B Arnolfo
Located next to Ponte di Campana, the Arnolfo is in the heart of the old town and within a few minutes stroll of the historic sights. Rooms have typical stone walls, timber ceilings and have an ensuite. If you wish to relax you can also take advantage of the guest reading room and small garden.
A short transfer takes you to the old town walls of Monteriggioni. Built in the medieval ages as a defence fort against Florence, little has changed since the 13th century, so do take time to explore the ancient ramparts and cobbled streets. Leaving the Monteriggioni, rejoin the Via Francigena as you begin a walk through wooded trails, wheat fields and across the flatlands of Pian de Lago. One final climb heads into the outskirts’ of Siena as you make your way to the finishing point of the elaborate Piazza del Campo.
Walk: 21km
Ascent: 330m
Descent: 260m
Meals included: Breakfast
Accommodation: Hotel Chiusarelli
Round off your week with a night in a typical neoclassical villa dating back to the 1870s. Located in the historical centre, several years ago the hotel was refurbished to a traditional Sienese house, complete with large, beautiful preserved frescos. A charming and fitting end to your walking trip.
Depending on your onward travel arrangements, we’d suggest an early morning stroll around the streets of Siena and the Piazza del Campo before the buzz of the crowds descend into the streets.
Meals included: Breakfast
During this tour, you will spend each night in small family-run boutique B&B’s and 3* hotels. Chosen for their location, facilities and history, each accommodation is used to welcoming walkers. As many of them will be family-run your hosts are very knowledgeable about each of the towns you will stay in. They will always be happy to chat with you about the history, food and wine. Of course, you can always call us too should you need anything during your walk. 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 5 breakfasts, 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 walk as moderate. Tracks and trails may have short steep hill sections and rough surfaces. A moderate active lifestyle makes the walking 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 15km 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 roads. 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 beginnings 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 Volterra and ends in Siena. Volterra does not have an airport, but nearby Siena has excellent train links to the Pisa, Florence and Rome airports. From Siena, we can arrange a private transfer for you or you can use the public transport links to Volterra.
Florence airport
Take the airport train directly into the Florence centre. Here you can change for a direct train service to Siena (approx 2 hrs).
Pisa Airport
On arrival at Pisa Airport, you can take the ‘Pisa Mover’ train shuttle to the Pisa Centrale station to change for services to Siena (changing in Empoli). Journey time is between 1hr 30mins – 2hrs.
Rome Airport
Rome has two airports. Fiumicino and Ciampino. Fiumicino airport connects through to Florence Central station in around 2hrs 30mins (with a change of trains in Rome central station). If you’re arriving at Rome Ciampino airport you will need to take the airport bus to Ciampino station and change at Rome central station for services to Siena. Journey time from Ciampino to Siena is around 2hrs 30mins (depending on times and services).
Siena does not have an airport but does have excellent train connections to Florence (direct service, 1hr 30mins), Pisa (change at Empoli, 1hr 45mins) and Rome (via Chiusi Chianciano Terme, 4hrs or via Florence, 3hrs 15mins).
For all train travel in Italy prices, timetables and ticket reservations can be made through The Trainline or Tren Italia.
Another useful generic 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
Walk across a timeless region of Tuscany to the medieval hilltop towns of Volterra, San Gimignano and Monteriggioni. Follow ancient Etruscan trails and pilgrim routes through vineyards and olive groves ending in the majestic Piazza del Campo in Siena.
The walk begins deep in the heart of Tuscany at Volterra, one of the most ancient Etruscan settlements. Set atop a high plateau, explore its labyrinth of cobbled streets awash with Roman and medieval architecture. Head east across a rolling landscape peppered with sleepy hamlets as the impressive 14 medieval towers of San Gimignano come into view.
Continue on your journey to Siena along the pilgrim route, Via Francigena. As thousands of pilgrims would have before you, walk the classic white gravel roads stopping to explore the perfectly preserved 13th-century walled town of Monteriggioni. The final day of this Tuscan discovery ends in Siena’s lively Piazza del Campo, the perfect spot to kick back and relax with an Aperol Spritz.
Today arrive at leisure into the old town of Volterra. Built on a high plateau, Volterra was once a trading powerhouse and although the old town is only a third of its original size, it is a joy to explore. Wander through a maze of cobbled streets, crammed with gorgeously preserved Etruscan, Roman and mediev
Today arrive at leisure into the old town of Volterra. Built on a high plateau, Volterra was once a trading powerhouse and although the old town is only a third of its original size, it is a joy to explore. Wander through a maze of cobbled streets, crammed with gorgeously preserved Etruscan, Roman and medieval architecture. Later in the evening, you will dine at a nearby restaurant to your hotel.
Accommodation: Hotel Volterra Inn
Located within the 5th-century walls of historic Volterra, the hotel is classically yet simply designed. All the rooms have an en-suite and there is a hotel bar open in the evenings, where you can enjoy an Aperol Spritz.
The day starts with a private transfer to the trailhead near Podere Fontanelle. Follow rural trails through the woodland of Castelvecchio nature reserve and into the sleepy hamlet of San Donato, nestled in the classic picture-postcard landscape. Nearing San Gimignano you’ll begin to see its Manhattan-like skyline of medieval towers. One of the most visited villages in Italy, the UNESCO listed historic centre is incredibly well preserved and is a step back in time to when the aristocracy of the 12th and 13th centuries flaunted their wealth by constructing the most elaborate of towers.
Walk: 16km
Ascent: 250m
Descent: 530m
Meals included: Breakfast
Accommodation: Hotel la Cisterna
Overlooking the Piazza Cisterna, the property has been at the heart of San Gimignano for over 1000 years. Rooms have views of the cobbled square, buzzing with life, or looking out over the vineyards and rooftops of the countryside. Restaurants and bars are only a few steps away and as you’re here for 2 nights there is also an opportunity to visit Gelateria Dondoli, a previous winner of the world’s best gelato shop.
Immerse yourself in classic Tuscan countryside as you spend the day walking through the villages and vineyards east of San Gimignano. Follow the traditional white gravel roads (strade bianche) which are a defining feature of Tuscany. Pass through the historic settlements of Poggio Casaglia and Poggio Alloro where you can enjoy a picnic under the olive trees or have lunch in a traditional Fattoria. On return to San Gimignano, you’ll soon see the familiar towers before arriving into the bustle of the historic centre.
Walk: 16km
Ascent: 500m
Descent: 500m
Meals included: Breakfast
Accommodation: Hotel la Cisterna
Today follow the Via Francigena, an ancient pilgrim route starting in Canterbury, England and finishing in Rome which has been walked by pilgrims since the 6th century. Not long after leaving San Gimignano, you’ll be back enjoying the gorgeous Tuscan countryside, including vineyards, as you head south towards Colle Di Val D’Elsa. This is a beautiful amble through a Tuscan la
Today follow the Via Francigena, an ancient pilgrim route starting in Canterbury, England and finishing in Rome which has been walked by pilgrims since the 6th century. Not long after leaving San Gimignano, you’ll be back enjoying the gorgeous Tuscan countryside, including vineyards, as you head south towards Colle Di Val D’Elsa. This is a beautiful amble through a Tuscan landscape of olive groves and vineyards, the route descends into the new town and shortly after into the charming medieval centre and relaxed piazza.
Walk: 13.5km
Ascent: 280m
Descent: 430m
Meals included: Breakfast
Accommodation: B&B Arnolfo
Located next to Ponte di Campana, the Arnolfo is in the heart of the old town and within a few minutes stroll of the historic sights. Rooms have typical stone walls, timber ceilings and have an ensuite. If you wish to relax you can also take advantage of the guest reading room and small garden.
ndscape of olive groves and vineyards, the route descends into the new town and shortly after into the charming medieval centre and relaxed piazza.
Walk: 13.5km
Ascent: 280m
Descent: 430m
Meals included: Breakfast
Accommodation: B&B Arnolfo
Located next to Ponte di Campana, the Arnolfo is in the heart of the old town and within a few minutes stroll of the historic sights. Rooms have typical stone walls, timber ceilings and have an ensuite. If you wish to relax you can also take advantage of the guest reading room and small garden.
A short transfer takes you to the old town walls of Monteriggioni. Built in the medieval ages as a defence fort against Florence, little has changed since the 13th century, so do take time to explore the ancient ramparts and cobbled streets. Leaving the Monteriggioni, rejoin the Via Francigena as you begin a walk through wooded trails, wheat fields and across the flatlands of Pian de Lago. One final climb heads into the outskirts’ of Siena as you make your way to the finishing point of the elaborate Piazza del Campo.
Walk: 21km
Ascent: 330m
Descent: 260m
Meals included: Breakfast
Accommodation: Hotel Chiusarelli
Round off your week with a night in a typical neoclassical villa dating back to the 1870s. Located in the historical centre, several years ago the hotel was refurbished to a traditional Sienese house, complete with large, beautiful preserved frescos. A charming and fitting end to your walking trip.
Depending on your onward travel arrangements, we’d suggest an early morning stroll around the streets of Siena and the Piazza del Campo before the buzz of the crowds descend into the streets.
Meals included: Breakfast
During this tour, you will spend each night in small family-run boutique B&B’s and 3* hotels. Chosen for their location, facilities and history, each accommodation is used to welcoming walkers. As many of them will be family-run your hosts are very knowledgeable about each of the towns you will stay in. They will always be happy to chat with you about the history, food and wine. Of course, you can always call us too should you need anything during your walk. 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 5 breakfasts, 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 walk as moderate. Tracks and trails may have short steep hill sections and rough surfaces. A moderate active lifestyle makes the walking 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 15km 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 roads. 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 beginnings 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 Volterra and ends in Siena. Volterra does not have an airport, but nearby Siena has excellent train links to the Pisa, Florence and Rome airports. From Siena, we can arrange a private transfer for you or you can use the public transport links to Volterra.
Florence airport
Take the airport train directly into the Florence centre. Here you can change for a direct train service to Siena (approx 2 hrs).
Pisa Airport
On arrival at Pisa Airport, you can take the ‘Pisa Mover’ train shuttle to the Pisa Centrale station to change for services to Siena (changing in Empoli). Journey time is between 1hr 30mins – 2hrs.
Rome Airport
Rome has two airports. Fiumicino and Ciampino. Fiumicino airport connects through to Florence Central station in around 2hrs 30mins (with a change of trains in Rome central station). If you’re arriving at Rome Ciampino airport you will need to take the airport bus to Ciampino station and change at Rome central station for services to Siena. Journey time from Ciampino to Siena is around 2hrs 30mins (depending on times and services).
Siena does not have an airport but does have excellent train connections to Florence (direct service, 1hr 30mins), Pisa (change at Empoli, 1hr 45mins) and Rome (via Chiusi Chianciano Terme, 4hrs or via Florence, 3hrs 15mins).
For all train travel in Italy prices, timetables and ticket reservations can be made through The Trainline or Tren Italia.
Another useful generic 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
The notes were comprehensive and mostly accurate. The accommodation choices were excellent – lovely, characterful places – and the luggage transfer was seamless throughout, which helped a great deal. So good to arrive at your accommodation and know that there are dry clothes waiting! I also greatly appreciated the provision of support materials such as maps and GPS routes, and emergency phone numbers. I did use some of these extras and they gave me considerable peace of mind.
Q: What happens if I don’t want to walk on one of the days?
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 (although it can be very limited). 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 any 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 Siena?
Of course, please let us know at the time of booking if you would like to extend your time in Siena. There is so much to see, we’d suggest at least 1 extra night.
Q: Can my children walk with me?
This trip cannot be booked for under 16's. We aren't able to offer discounted rates for children.
Q: We’re travelling as friends, can we get a triple room?
Triple rooms are in limited availability. Some accommodations do not offer triple rooms but we can always provide a twin or double room with a single room.
Q: Can we reduce the days walked?
Easily! This tour has been created with flexibility in mind. You can easily remove the loop walk in San Gimignano on day 3 and if you already have plans to be in Volterra before starting the walk, we can collect you on day 1 and take you directly to the start of the walk. We’re always happy to discuss your needs.
Q: Can we extend the days walked?
Of course, you may want to start by walking Siena to Montepulciano which is 8 days and fits perfectly by starting in Siena.
Richard Y
The notes were comprehensive and mostly accurate. The accommodation choices were excellent – lovely, characterful places – and the luggage transfer was seamless throughout, which helped a great deal. So good to arrive at your accommodation and know that there are dry clothes waiting! I also greatly appreciated the provision of support materials such as maps and GPS routes, and emergency phone numbers. I did use some of these extras and they gave me considerable peace of mind.