OVERVIEW

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 pilgrims 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. Along the way, enjoy encounters with villagers and winemakers. 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, sample many of the fine wines, including the award winning, Vino Nobile.

 

HIGHLIGHTS:

  • Walk from Siena, through Tuscany’s Val d’Orcia region to Montepulciano
  • Hangout in the glorious ‘Piazza del Campo’ in Siena
  • Sample the award-winning Brunello wines of Montalcino
  • Walk through classic, rolling Tuscan landscape
  • Soak in the thermal baths of Bagno Vignoni
  • Visit medieval abbeys, hilltop towers and Romanesque churches
  • Dine on rustic dishes of Tortello pasta with ragu
  • Spend each night in classic Tuscan townhouse or rural hotels
  • Explore the Renaissance town of Montepulciano

WALK OVERVIEW

TYPE OF WALK
SELF GUIDED
TRIP LENGTH
8 DAYS
WALK GRADE
Moderate

Grade 3 – Moderate

Short, steep hill sections. Moderate active lifestyle and some walking experience recommended.

PRICE FROM
$ 2455

per person twin/double share

SINGLE OCCUPANCY
$ 1295

Accommodations charge the same price per room regardless of whether there are one or two people occupying it. To cover the cost of the accommodation when occupied by one person we need to charge the single occupancy fee.

per person

Book now

ITINERARY

  • Day 1
  • Day 2
  • Day 3
  • Day 4
  • Day 5
  • Day 6
  • Day 7
  • Day 8

DAY 1
Arrive Siena

On arrival to Siena, head to the dramatic Piazza del Campo. Formerly the meeting point of 3 major routes in and out of Siena, the piazza was developed as a neutral meeting ground where political holidays and festivals could be staged. A unique design, said to be in the shape of Virgin Mary’s cloak, the piazza thrives with tourists and twice a year hosts the colourful Palio horse event.

Meals included: None
Accommodation: Hotel Chiusarelli
Start your Tuscan week of walking with a night in a typical neoclassical villa dating back to the 1870’s. Located in the historical centre, several years ago the hotel was refurbished to a traditional Sienese house, complete with a large, beautiful preserved frescos. A charming and fitting end to your walking trip.

DAY 2
Walk to Monteroni d'Arbia, transfer to Buonconvento

From the magnificent Piazza del Campo, depart Siena on foot as you follow sections of the ancient pilgrim route, ‘Via Francigena’ (which starts in Canterbury, southern England and ends in St Peter’s Square, Rome). The trail heads through the ‘Crete Senesi’ landscape to Monteroni d’Arbia and along typical ‘Strade Bianchi’ (Tuscan white gravel roads). On arrival at Monteroni d’Arbia, a short, private transfer (10mins) will take you to your rural accommodation in the hills above Buonconvento.

Walk: 21km
Ascent: 160m
Descent: 330m
Meals included: Breakfast & Dinner
Accommodation: Pieve a Salti
Nestled deep in the Tuscan countryside at this agriturismo. Relax poolside, overlooking the countryside or head to the spa for a reviving leg massage. Pieve a Salti is a working farm, run by the Parandi family who cultivate over 700 hectares of land for local produce (much of which you will sample during your stay here).

DAY 3
Walk to Montalcino

Begin the day with a short transfer to Buonconvento (10mins) and wander along its historical centre, Via Soccini. Leaving   Continue walking through the iconic Senese landscapes, along trails and strade bianchi (white roads) lined with the towering and elegant cypress trees and through the Brunello vineyards, using 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 & Lunch
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 Van d’Arbia, which can also be viewed from your room, which have a typical Tuscan decor.

DAY 4
Walk to Castelnuovo dell’Abate, transfer to Bagno Vignoni

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.

DAY 5
Walk to Pienza

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, enjoy breakfast on the terrace with views that stretch out over golden wheat fields and vineyards.

DAY 6
Walk to Montepulciano

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 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 and to see the sun set over the Val d’Orcia.

Walk: 15km
Ascent: 550m
Descent: 450m
Meals included: Breakfast & Walkers Lunch
Accommodation: Hotel Il 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.

DAY 7
Explore Montepulciano / optional walk to Montefollonico

North of Montepulciano is the delightful hilltop hamlet of Montefollonico overlooking the Val d’Orcia and Valdichianna. A 13th century walled town, the Church of San Leonardo has become one of the most important examples of Romanesque architecture within southern Tuscany. If you’d prefer an easier day, it is possible to take local transport to Montefollonico or simply head back in the cavernous streets of Montepulciano and further acquaint your palette with the diverse and delicious red wines produced in the region.

Walk: 18.5km (or 9km and return by bus)
Ascent: 665m
Descent: Descent: 665m
Meals included: Breakfast
Accommodation: Hotel Il Rondo

DAY 8
Onward Travel

From Montepulciano the nearby train station, Chiusi Chianterme has regular connections through to Florence, Pisa and Siena. You may also have time to further explore the streets or Montepulciano or relax in the garden of your hotel.

Meals included: Breakfast

WHAT’S INCLUDED

  • 7 nights ensuite room accommodation in Guesthouses, 3* & 4* Hotels
  • All luggage transfers
  • All taxi transfers as described in the itinerary
  • Option to upgrade to a wine resort in Gaiole in Chianti
  • 6 breakfasts 2 lunches and 1 dinner
  • Maps, daily walk notes and information pack
  • 24/7 telephone support
  • Flexible itinerary to suit your walking needs
  • Enjoy worry free navigation with your comprehensive maps, route notes and guidebook

ACCOMMODATION & DINING

OVERVIEW

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 Chianti 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 7 breakfasts and 2 lunches and 1 dinner. 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.

GENERAL INFO

About the walking

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 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 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 for your own device.

Availability

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 mark 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.

How to get there and away

This walk starts in Siena and ends in Montepulciano, both are very easy to reach by train.

Onward Travel From Siena

From Pisa you can take a special “people mover” from the airport to the Pisa Centrale Train Station and then a train to Siena. They leave every 30 mins, with one change, the full journey takes approximately 1hr 45min. From Rome you can take a Leonardo Express Train into Rome centre and then a train to Siena (however you have to go to Florence, then change). The trains leave approximately every hour and the journey will take approximately 3hrs 30min. From Florence you can take a train to Siena. The journey time is about 1hr 30min. Some trains are direct whereas on others you will have to change in Empoli.

Another useful planning tool for travel is Rome2Rio should you be travelling from, or to, other destinations.

Insurance

We strongly recommend the purchase of travel insurance for all of our trips. We require that you purchase a travel insurance policy for all travel overseas, as we charge a cancellation fee if you cancel your walking holiday after we have confirmed it. It is also important in the event of an accident or loss of property.  See FAQ’s for more information.

MAP

DEPARTURE DATES

  • DATES
    AVAILABILITY
    PRICE
    Single Occupancy
    DETAILS
  • 22 Aug 2020 - 20 Oct 2020
    AVAILABLE
    from

    $2455

    SINGLE OCCUPANCY
    $1295

    Not available from 1st July – 22nd August

  • 4 Apr 2021 - 31 Oct 2021
    AVAILABLE
    from

    $2575

    SINGLE OCCUPANCY
    $1345

    Not available from 1st July – 22nd August

FAQS

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: Is this tour OK for solo walkers?

Yes this tour is ok for solo walkers. It is likely that you’ll bump into other walkers along the trails and in many of the places you will stay. You will also pass through villages and towns should you need any assistance. Generally there is always good network coverage for mobile phones, should you worry about walking alone.

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.

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Overview

OVERVIEW

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 pilgrims 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. Along the way, enjoy encounters with villagers and winemakers. 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, sample many of the fine wines, including the award winning, Vino Nobile.

 

HIGHLIGHTS:

  • Walk from Siena, through Tuscany’s Val d’Orcia region to Montepulciano
  • Hangout in the glorious ‘Piazza del Campo’ in Siena
  • Sample the award-winning Brunello wines of Montalcino
  • Walk through classic, rolling Tuscan landscape
  • Soak in the thermal baths of Bagno Vignoni
  • Visit medieval abbeys, hilltop towers and Romanesque churches
  • Dine on rustic dishes of Tortello pasta with ragu
  • Spend each night in classic Tuscan townhouse or rural hotels
  • Explore the Renaissance town of Montepulciano

WALK OVERVIEW

TYPE OF WALK
SELF GUIDED
TRIP LENGTH
8 DAYS
WALK GRADE
Moderate

Grade 3 – Moderate

Short, steep hill sections. Moderate active lifestyle and some walking experience recommended.

PRICE FROM
$ 2455

per person twin/double share

SINGLE OCCUPANCY
$ 1295

Accommodations charge the same price per room regardless of whether there are one or two people occupying it. To cover the cost of the accommodation when occupied by one person we need to charge the single occupancy fee.

per person

Book now
Itinerary

ITINERARY

  • Day 1
  • Day 2
  • Day 3
  • Day 4
  • Day 5
  • Day 6
  • Day 7
  • Day 8

DAY 1
Arrive Siena

On arrival to Siena, head to the dramatic Piazza del Campo. Formerly the meeting point of 3 major routes in and out of Siena, the piazza was developed as a neutral meeting ground where political holidays and festivals could be staged. A unique design, said to be in the shape of Virgin Mary’s cloak, the piazza thrives with tourists and twice a year hosts the colourful Palio horse event.

Meals included: None
Accommodation: Hotel Chiusarelli
Start your Tuscan week of walking with a night in a typical neoclassical villa dating back to the 1870’s. Located in the historical centre, several years ago the hotel was refurbished to a traditional Sienese house, complete with a large, beautiful preserved frescos. A charming and fitting end to your walking trip.

DAY 2
Walk to Monteroni d'Arbia, transfer to Buonconvento

From the magnificent Piazza del Campo, depart Siena on foot as you follow sections of the ancient pilgrim route, ‘Via Francigena’ (which starts in Canterbury, southern England and ends in St Peter’s Square, Rome). The trail heads through the ‘Crete Senesi’ landscape to Monteroni d’Arbia and along typical ‘Strade Bianchi’ (Tuscan white gravel roads). On arrival at Monteroni d’Arbia, a short, private transfer (10mins) will take you to your rural accommodation in the hills above Buonconvento.

Walk: 21km
Ascent: 160m
Descent: 330m
Meals included: Breakfast & Dinner
Accommodation: Pieve a Salti
Nestled deep in the Tuscan countryside at this agriturismo. Relax poolside, overlooking the countryside or head to the spa for a reviving leg massage. Pieve a Salti is a working farm, run by the Parandi family who cultivate over 700 hectares of land for local produce (much of which you will sample during your stay here).

DAY 3
Walk to Montalcino

Begin the day with a short transfer to Buonconvento (10mins) and wander along its historical centre, Via Soccini. Leaving   Continue walking through the iconic Senese landscapes, along trails and strade bianchi (white roads) lined with the towering and elegant cypress trees and through the Brunello vineyards, using 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 & Lunch
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 Van d’Arbia, which can also be viewed from your room, which have a typical Tuscan decor.

DAY 4
Walk to Castelnuovo dell’Abate, transfer to Bagno Vignoni

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.

DAY 5
Walk to Pienza

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, enjoy breakfast on the terrace with views that stretch out over golden wheat fields and vineyards.

DAY 6
Walk to Montepulciano

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 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 and to see the sun set over the Val d’Orcia.

Walk: 15km
Ascent: 550m
Descent: 450m
Meals included: Breakfast & Walkers Lunch
Accommodation: Hotel Il 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.

DAY 7
Explore Montepulciano / optional walk to Montefollonico

North of Montepulciano is the delightful hilltop hamlet of Montefollonico overlooking the Val d’Orcia and Valdichianna. A 13th century walled town, the Church of San Leonardo has become one of the most important examples of Romanesque architecture within southern Tuscany. If you’d prefer an easier day, it is possible to take local transport to Montefollonico or simply head back in the cavernous streets of Montepulciano and further acquaint your palette with the diverse and delicious red wines produced in the region.

Walk: 18.5km (or 9km and return by bus)
Ascent: 665m
Descent: Descent: 665m
Meals included: Breakfast
Accommodation: Hotel Il Rondo

DAY 8
Onward Travel

From Montepulciano the nearby train station, Chiusi Chianterme has regular connections through to Florence, Pisa and Siena. You may also have time to further explore the streets or Montepulciano or relax in the garden of your hotel.

Meals included: Breakfast

What’s Included

WHAT’S INCLUDED

  • 7 nights ensuite room accommodation in Guesthouses, 3* & 4* Hotels
  • All luggage transfers
  • All taxi transfers as described in the itinerary
  • Option to upgrade to a wine resort in Gaiole in Chianti
  • 6 breakfasts 2 lunches and 1 dinner
  • Maps, daily walk notes and information pack
  • 24/7 telephone support
  • Flexible itinerary to suit your walking needs
  • Enjoy worry free navigation with your comprehensive maps, route notes and guidebook
Accommodation & Dining

ACCOMMODATION & DINING

OVERVIEW

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 Chianti 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 7 breakfasts and 2 lunches and 1 dinner. 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.

General Info

GENERAL INFO

About the walking

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 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 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 for your own device.

Availability

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 mark 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.

How to get there and away

This walk starts in Siena and ends in Montepulciano, both are very easy to reach by train.

Onward Travel From Siena

From Pisa you can take a special “people mover” from the airport to the Pisa Centrale Train Station and then a train to Siena. They leave every 30 mins, with one change, the full journey takes approximately 1hr 45min. From Rome you can take a Leonardo Express Train into Rome centre and then a train to Siena (however you have to go to Florence, then change). The trains leave approximately every hour and the journey will take approximately 3hrs 30min. From Florence you can take a train to Siena. The journey time is about 1hr 30min. Some trains are direct whereas on others you will have to change in Empoli.

Another useful planning tool for travel is Rome2Rio should you be travelling from, or to, other destinations.

Insurance

We strongly recommend the purchase of travel insurance for all of our trips. We require that you purchase a travel insurance policy for all travel overseas, as we charge a cancellation fee if you cancel your walking holiday after we have confirmed it. It is also important in the event of an accident or loss of property.  See FAQ’s for more information.

Map

MAP

Departure Dates

DEPARTURE DATES

  • DATES
    AVAILABILITY
    PRICE
    Single Occupancy
    DETAILS
  • 22 Aug 2020 - 20 Oct 2020
    AVAILABLE
    Details
    from

    $2455

    SINGLE OCCUPANCY
    $1295
  • 4 Apr 2021 - 31 Oct 2021
    AVAILABLE
    Details
    from

    $2575

    SINGLE OCCUPANCY
    $1345
Faqs

FAQS

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: Is this tour OK for solo walkers?

Yes this tour is ok for solo walkers. It is likely that you’ll bump into other walkers along the trails and in many of the places you will stay. You will also pass through villages and towns should you need any assistance. Generally there is always good network coverage for mobile phones, should you worry about walking alone.

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.

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