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SELF-GUIDED
10 DAYS
Moderate
Immerse yourself in Tuscan landscapes of olive groves, cypress trees and vineyards on this self-guided walking exploration. Between the artistic opulence of Florence and the Renaissance piazzas of Montepulciano, discover the wine towns of Chianti and follow ancient pilgrim trails through the agricultural riches of Val d’Orcia.
Wander the impressive streets of Florence and visit the Uffizi gallery where the Renaissance masterpieces of Caravaggio, Botticelli and Da Vinci hang. Walk to the Etruscan founded wine towns of Radda and Gaiole in Chianti and explore the medieval majesty of Siena. Venture deep into UNESCO protected land of Val d’Orcia and enjoy the Roman way of life, soaking in the hot springs of Bagno Vignoni. Sample fine Brunello wines in Montalcino and hike up to Pienza with breathtaking views across Val d’Orcia. Stay in traditional Tuscan family-run hotels and round off this unforgettable journey in the sleepy piazzas of Montepulciano.
The Cradle of the Renaissance, Florence is a city of fine art, fashion and exceptional architecture. Many of Florence’s sights need little introduction. Stroll across the medieval Ponte Vecchio bridge and head to the world-famous Uffizi art gallery where the masterpieces of Leonardo da Vinci and Raphael hang. Visit the Galleria dell’Accademia to see Michelangelo’s statue of David and walk through cobbled streets to Piazza del Duomo to marvel at the exquisite designs of Brunelleschi.
Accommodation: Hotel David
Located on the southern side the River Arno, the hotel is set in a 19th-century building only a couple of minutes’ walk from the Arno River. Classically furnished rooms have a free mini-bar and breakfast is well known for its selection of homemade pastries. The historic centre is a 5-minute bus journey, or you can enjoy a 20-minute riverside walk to Ponte Vecchio and cross into the splendour of Florence.
Transfer deep into the Chianti Winelands to begin your walk on a forested trail to the fortified village of Volpaia, home of the revered Volpaia red wine (a must to sample while you are here). Steeped in winemaking tradition, the town has been producing wine since the late 12th century. Beyond Volpaia, the trail follows typical ‘white roads’ lined with cypress trees as you ascend to the hilltop church of Santa Maria Novella (which has retained its original Romanesque structure). The trail rolls on through vineyards to the hilltop town of Radda in Chianti, one of the most celebrated wine towns of the Chianti region.
Walk: 13.5km
Ascent: 500m
Descent: 660m
Meals included: Breakfast
Accommodation: Hotel Palazzo San Niccolo
An elegant 4* hotel in Radda’s the Ciacci and Palagi. Within the building is a peaceful courtyard where you can relax with a glass of local Chianti or head into the garden to soak up the Tuscan sun. Rooms have been classically designed, in keeping with the history of the building. Before you leave this hotel, do take time to visit the small sitting room with an incredibly well-preserved fresco that is said to be a symbol of unity between the 2 families.
A gentle start begins with a descent southwards to your destination today, Gaiole in Chianti. Walk through wooded valleys, vineyards and olive groves. Enjoy rambling through picture-postcard Tuscan landscapes, passing through the hamlets of San Giusto in Salcio and Adine. Descend into the sleepy streets of Gaiole in Chianti where you will spend the next two nights and have the opportunity to learn more of the Chianti wine production and signature Tuscan dishes of Gaiole in Chianti.
Walk: 12km
Ascent: 350m
Descent: 500m
Meals included: Breakfast
Accommodation: Cavarchino
A restored farmhouse on the outskirts of Gaiole, Cavarchino is a charming family-run bed and breakfast. On arrival, you can relax in the gardens or take a dip in the pool before strolling into the Gaiole centre for dinner. Your host, Irene is always happy to help out with any questions or assistance you might need whilst in Gaiole.
Walk through the medieval streets of Gaiole and into the rich Tuscan countryside as the route climbs to Castello di San Donato in Perano, a cluster of well-preserved 10th-century houses. Continue on through woodland trails which will see you arrive at the hamlet of Badia a Coltibuono. For over 1000 years the Coltibuono farm has been producing wines, olive oils and has been a great spot for lunch before walking to the hilltop village of Montegrossi. A gentle but straightforward ramble descends back to the tranquillity of Gaiole and your hotel.
Walk: 19.5km or 15km
Ascent: 660m or 400m
Descent: 600m or 250m
Meals included: Breakfast
Accommodation: Cavarchino
Follow trails across a rolling landscape of olive groves and vineyards of Castelle di Meteo where since 1256 much of the land has been dedicated to producing this prestigious wine. Onwards from Castelle, much of the land is cloaked in oak woods and you might be lucky enough to spot an elusive deer en-route. Arriving into Lecchi Chainti, little has changed in this delightful town since the 12th century. From Lecchi, a private transfer will take you onwards to Siena and a visit to Piazza del Campo, one of the largest medieval squares in the world.
Walk: 11km
Ascent: 350m
Descent: 300m
Meals included: Breakfast
Accommodation: Hotel Chiusarelli
Spend the 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.
Transfer by private transport to Buonconvento. Wander along its historical centre, Via Soccini. Continue walking through the iconic Sienese landscapes, along trails and the strade bianche (white roads) lined with the towering and elegant cypress trees and through the Brunello vineyards that grow Sangiovese grapes for world-class wine. The day ends with a climb up to the 14th-century hill town of Montalcino, nestled amongst the hills of the Val d’Orcia.
Walk: 18.5km
Ascent: 540m
Descent: 3170m
Meals included: Breakfast
Accommodation: Hotel dei Capitani
Dating back to the middle ages, Hotel dei Capitani is believed to have been used as a refuge for Sienese people fleeing the Florentine army. The hotel pool boasts splendid views across Val d’Orcia and Val d’Arbia, which can also be viewed from your room. All rooms have a typical Tuscan decor.
South of Montalcino, an easy-going route, rolls through classic Tuscan landscapes. Just before reaching the delightful town of Castelnuovo dell’Abate, take time to visit the Romanesque Abbey of Sant’Antimo, dating back to the 8th century. The monks at the abbey still meet seven times a day, so you may be fortunate to hear the medieval Gregorian chants. Above the abbey, the village of Castelnuovo is a superb stop for lunch. Later in the afternoon, a private transfer will take you on to the Roman spa town of Bagno Vignoni.
Walk: 12km
Ascent: 280m
Descent: 470m
Meals included: Breakfast
Accommodation: La Locanda Loggiato
Sisters Barbara and Sabrina have been welcoming guests to Bagno Vignoni for almost 20 years. Their 14th-century property has been lovingly restored with all en-suite rooms featuring terracotta flooring and traditional wooden beams. A place of relaxation, not all bedrooms have wi-fi (but it is available in communal areas). La Locanda is the perfect environment to relax in after a visit to the thermal baths just a few minutes away in the main piazza.
Begin the day with a rewarding stretch of uphill to Vignoni Alto, complete with its own fortress tower. Onto San Quirico d’Orcia, the route gently descends through rich agricultural lands. Located on the Via Francigena pilgrim route, in medieval times the beautifully preserved San Quirico d’Orcia was of significant strategic importance, linking Europe with Rome. Do make time to explore the town and enjoy lunch in one of the many rustic restaurants. Continuing onto the hilltop town of Pienza be sure to try the local Pecorino cheese made from sheep’s milk.
Walk: 19.5km or 15km
Ascent: 660m or 400m
Descent: 600m or 250m
Meals included: Breakfast
Accommodation: Hotel La Valle
Within a couple of minutes of Pienza’s historic centre, the hotel occupies a typical Tuscany stone building. Complete with a roof garden, panoramic breakfast room, bar and en-suite rooms, you can enjoy breakfast on the terrace with views that stretch out over golden wheat fields and vineyards.
Set across a rolling hilltop, the elegant town of Montepulciano boasts one of Tuscany’s oldest wine producers; Vino Nobile. Walk via the hamlet of Monticchiello through a patchwork of rolling fields as the trail climbs up to Montepulciano. Explore the labyrinth of cobbled streets, lined with elegant Renaissance palaces, former homes of nobility and hidden piazzas. At the heart of the town is the Piazza Grande, a wonderful setting to taste the rich variety of Montepulciano wines. In the evening it’s worth strolling out to the edge of the old town to see the sunset over the Val d’Orcia.
Walk: 15km
Ascent: 550m
Descent: 450m
Meals included: Breakfast
Accommodation: Hotel II Rondo
Located outside the lively town centre, the family-run Hotel II Rondo is tucked away in a peaceful corner of Montepulciano. After a day of walking and exploring, relax in the impeccably maintained gardens. In keeping with the period of the building, rooms have been decorated to an 18th-century style.
From Montepulciano the nearby train station, Chiusi Chianciano Terme has regular connections through to Florence, Pisa and Siena. You may also have time to further explore the streets of Montepulciano or relax in the garden of your hotel.
Meals included: Breakfast
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. Many of them will be family-run so are very knowledgeable about the region and 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. 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 9 breakfasts after each of the nights stay. There are many delicious options for you to choose from in Tuscany for lunch and dinner; your host will be able to provide recommendations if you’d like! 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 being moderate. Tracks and trails may have short steep hill sections and rough surfaces. A moderate active lifestyle makes 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 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 village 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 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 will begin to mark 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.
How to get there and away
This walk starts in Florence and ends in Montepulciano. Florence has a small airport, whereas the larger airports of Pisa 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.
Pisa Airport
From Pisa Airport you can take the ‘Pisa Mover’ train shuttle to the Pisa Centrale station to change for direct services to Florence. 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. 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 for Florence. Journey time from Ciampino to Florence is around 2hrs 30mins (depending on times and services).
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
Immerse yourself in Tuscan landscapes of olive groves, cypress trees and vineyards on this self-guided walking exploration. Between the artistic opulence of Florence and the Renaissance piazzas of Montepulciano, discover the wine towns of Chianti and follow ancient pilgrim trails through the agricultural riches of Val d’Orcia.
Wander the impressive streets of Florence and visit the Uffizi gallery where the Renaissance masterpieces of Caravaggio, Botticelli and Da Vinci hang. Walk to the Etruscan founded wine towns of Radda and Gaiole in Chianti and explore the medieval majesty of Siena. Venture deep into UNESCO protected land of Val d’Orcia and enjoy the Roman way of life, soaking in the hot springs of Bagno Vignoni. Sample fine Brunello wines in Montalcino and hike up to Pienza with breathtaking views across Val d’Orcia. Stay in traditional Tuscan family-run hotels and round off this unforgettable journey in the sleepy piazzas of Montepulciano.
The Cradle of the Renaissance, Florence is a city of fine art, fashion and exceptional architecture. Many of Florence’s sights need little introduction. Stroll across the medieval Ponte Vecchio bridge and head to the world-famous Uffizi art gallery where the masterpieces of Leonardo da Vinci and Raphael hang. Visit the Galleria dell’Accademia to see Michelangelo’s statue of David and walk through cobbled streets to Piazza del Duomo to marvel at the exquisite designs of Brunelleschi.
Accommodation: Hotel David
Located on the southern side the River Arno, the hotel is set in a 19th-century building only a couple of minutes’ walk from the Arno River. Classically furnished rooms have a free mini-bar and breakfast is well known for its selection of homemade pastries. The historic centre is a 5-minute bus journey, or you can enjoy a 20-minute riverside walk to Ponte Vecchio and cross into the splendour of Florence.
Transfer deep into the Chianti Winelands to begin your walk on a forested trail to the fortified village of Volpaia, home of the revered Volpaia red wine (a must to sample while you are here). Steeped in winemaking tradition, the town has been producing wine since the late 12th century. Beyond Volpaia, the trail follows typical ‘white roads’ lined with cypress trees as you ascend to the hilltop church of Santa Maria Novella (which has retained its original Romanesque structure). The trail rolls on through vineyards to the hilltop town of Radda in Chianti, one of the most celebrated wine towns of the Chianti region.
Walk: 13.5km
Ascent: 500m
Descent: 660m
Meals included: Breakfast
Accommodation: Hotel Palazzo San Niccolo
An elegant 4* hotel in Radda’s the Ciacci and Palagi. Within the building is a peaceful courtyard where you can relax with a glass of local Chianti or head into the garden to soak up the Tuscan sun. Rooms have been classically designed, in keeping with the history of the building. Before you leave this hotel, do take time to visit the small sitting room with an incredibly well-preserved fresco that is said to be a symbol of unity between the 2 families.
A gentle start begins with a descent southwards to your destination today, Gaiole in Chianti. Walk through wooded valleys, vineyards and olive groves. Enjoy rambling through picture-postcard Tuscan landscapes, passing through the hamlets of San Giusto in Salcio and Adine. Descend into the sleepy streets of Gaiole in Chianti where you will spend the next two nights and have the opportunity to learn more of the Chianti wine production and signature Tuscan dishes of Gaiole in Chianti.
Walk: 12km
Ascent: 350m
Descent: 500m
Meals included: Breakfast
Accommodation: Cavarchino
A restored farmhouse on the outskirts of Gaiole, Cavarchino is a charming family-run bed and breakfast. On arrival, you can relax in the gardens or take a dip in the pool before strolling into the Gaiole centre for dinner. Your host, Irene is always happy to help out with any questions or assistance you might need whilst in Gaiole.
Walk through the medieval streets of Gaiole and into the rich Tuscan countryside as the route climbs to Castello di San Donato in Perano, a cluster of well-preserved 10th-century houses. Continue on through woodland trails which will see you arrive at the hamlet of Badia a Coltibuono. For over 1000 years the Coltibuono farm has been producing wines, olive oils and has been a great spot for lunch before walking to the hilltop village of Montegrossi. A gentle but straightforward ramble descends back to the tranquillity of Gaiole and your hotel.
Walk: 19.5km or 15km
Ascent: 660m or 400m
Descent: 600m or 250m
Meals included: Breakfast
Accommodation: Cavarchino
Follow trails across a rolling landscape of olive groves and vineyards of Castelle di Meteo where since 1256 much of the land has been dedicated to producing this prestigious wine. Onwards from Castelle, much of the land is cloaked in oak woods and you might be lucky enough to spot an elusive deer en-route. Arriving into Lecchi Chainti, little has changed in this delightful town since the 12th century. From Lecchi, a private transfer will take you onwards to Siena and a visit to Piazza del Campo, one of the largest medieval squares in the world.
Walk: 11km
Ascent: 350m
Descent: 300m
Meals included: Breakfast
Accommodation: Hotel Chiusarelli
Spend the 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.
Transfer by private transport to Buonconvento. Wander along its historical centre, Via Soccini. Continue walking through the iconic Sienese landscapes, along trails and the strade bianche (white roads) lined with the towering and elegant cypress trees and through the Brunello vineyards that grow Sangiovese grapes for world-class wine. The day ends with a climb up to the 14th-century hill town of Montalcino, nestled amongst the hills of the Val d’Orcia.
Walk: 18.5km
Ascent: 540m
Descent: 3170m
Meals included: Breakfast
Accommodation: Hotel dei Capitani
Dating back to the middle ages, Hotel dei Capitani is believed to have been used as a refuge for Sienese people fleeing the Florentine army. The hotel pool boasts splendid views across Val d’Orcia and Val d’Arbia, which can also be viewed from your room. All rooms have a typical Tuscan decor.
South of Montalcino, an easy-going route, rolls through classic Tuscan landscapes. Just before reaching the delightful town of Castelnuovo dell’Abate, take time to visit the Romanesque Abbey of Sant’Antimo, dating back to the 8th century. The monks at the abbey still meet seven times a day, so you may be fortunate to hear the medieval Gregorian chants. Above the abbey, the village of Castelnuovo is a superb stop for lunch. Later in the afternoon, a private transfer will take you on to the Roman spa town of Bagno Vignoni.
Walk: 12km
Ascent: 280m
Descent: 470m
Meals included: Breakfast
Accommodation: La Locanda Loggiato
Sisters Barbara and Sabrina have been welcoming guests to Bagno Vignoni for almost 20 years. Their 14th-century property has been lovingly restored with all en-suite rooms featuring terracotta flooring and traditional wooden beams. A place of relaxation, not all bedrooms have wi-fi (but it is available in communal areas). La Locanda is the perfect environment to relax in after a visit to the thermal baths just a few minutes away in the main piazza.
Begin the day with a rewarding stretch of uphill to Vignoni Alto, complete with its own fortress tower. Onto San Quirico d’Orcia, the route gently descends through rich agricultural lands. Located on the Via Francigena pilgrim route, in medieval times the beautifully preserved San Quirico d’Orcia was of significant strategic importance, linking Europe with Rome. Do make time to explore the town and enjoy lunch in one of the many rustic restaurants. Continuing onto the hilltop town of Pienza be sure to try the local Pecorino cheese made from sheep’s milk.
Walk: 19.5km or 15km
Ascent: 660m or 400m
Descent: 600m or 250m
Meals included: Breakfast
Accommodation: Hotel La Valle
Within a couple of minutes of Pienza’s historic centre, the hotel occupies a typical Tuscany stone building. Complete with a roof garden, panoramic breakfast room, bar and en-suite rooms, you can enjoy breakfast on the terrace with views that stretch out over golden wheat fields and vineyards.
Set across a rolling hilltop, the elegant town of Montepulciano boasts one of Tuscany’s oldest wine producers; Vino Nobile. Walk via the hamlet of Monticchiello through a patchwork of rolling fields as the trail climbs up to Montepulciano. Explore the labyrinth of cobbled streets, lined with elegant Renaissance palaces, former homes of nobility and hidden piazzas. At the heart of the town is the Piazza Grande, a wonderful setting to taste the rich variety of Montepulciano wines. In the evening it’s worth strolling out to the edge of the old town to see the sunset over the Val d’Orcia.
Walk: 15km
Ascent: 550m
Descent: 450m
Meals included: Breakfast
Accommodation: Hotel II Rondo
Located outside the lively town centre, the family-run Hotel II Rondo is tucked away in a peaceful corner of Montepulciano. After a day of walking and exploring, relax in the impeccably maintained gardens. In keeping with the period of the building, rooms have been decorated to an 18th-century style.
From Montepulciano the nearby train station, Chiusi Chianciano Terme has regular connections through to Florence, Pisa and Siena. You may also have time to further explore the streets of Montepulciano or relax in the garden of your hotel.
Meals included: Breakfast
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. Many of them will be family-run so are very knowledgeable about the region and 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. 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 9 breakfasts after each of the nights stay. There are many delicious options for you to choose from in Tuscany for lunch and dinner; your host will be able to provide recommendations if you’d like! 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 being moderate. Tracks and trails may have short steep hill sections and rough surfaces. A moderate active lifestyle makes 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 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 village 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 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 will begin to mark 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.
How to get there and away
This walk starts in Florence and ends in Montepulciano. Florence has a small airport, whereas the larger airports of Pisa 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.
Pisa Airport
From Pisa Airport you can take the ‘Pisa Mover’ train shuttle to the Pisa Centrale station to change for direct services to Florence. 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. 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 for Florence. Journey time from Ciampino to Florence is around 2hrs 30mins (depending on times and services).
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
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 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 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 also 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?
Florence. With so much world-famous Renaissance art and delicious food to sample, Florence is worthy of an extra day. From Florence you can also hop on the train to nearby Pisa (1-hour journey) to see the world-famous leaning tower. Radda in Chianti and / or Gaiole in Chianti Historic towns which are best experience by relaxing poolside at your hotel, sampling the locally produced Chianti. In the evening enjoy typical dishes such as pappa al pomodoro, beef ragu pasta and wild boar stew. 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 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?
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 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 Gaiole in Chianti on day 5 and if you already have plans to be in Florence, we can collect you in Florence and take you directly to Greve in Chianti on day 1. We’re always happy to discuss your needs.
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.
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.