OVERVIEW

Walk and explore Tuscany from Volterra via the medieval powerhouse of Siena and the hilltop town of San Gimignano. From Siena, hike across the UNESCO-protected Val d’Orcia region to the elegant hilltop town of Montepulciano. Follow sections of the ancient pilgrim’s path, via Francigena, deep into a landscape of soft rolling hills and avenues of towering cypress trees. Explore the 16th-century wine town of Montalcino, renowned for its precious Brunello wine and enjoy the Roman way of life, soaking in the hot springs of Bagno Vignoni.

This is a moderate graded ramble through chestnut groves, vineyards and across classic Tuscan landscapes. Visit the hilltop hamlets of Castelnuovo dell’Abate and Monticchiello, among many other stunning Tuscany villages.

Highlights

  • Walk from Volterra, via Sienna through Tuscany’s Val d’Orcia region, to Montepulciano
  • Hang out in the glorious ‘Piazza del Campo’ in Siena and in the hilltop town of San Gimignano
  • Sample the award-winning Brunello wines of Montalcino
  • Soak in the thermal baths of Bagno Vignoni
  • Visit medieval abbeys, hilltop towers and Romanesque churches
  • Explore the Renaissance town of Montepulciano
  • Spend each night in classic Tuscan townhouses or rural hotels

WALK OVERVIEW

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

Grade 3 – Moderate

Short, steep hill sections. Walks that are longer than 12km with varied terrain. A moderate active lifestyle and some walking experience is recommended.

PRICE FROM
$ 3195

per person twin/double share

SINGLE OCCUPANCY
$ 1195

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

per person

  • 30+ years

  • eco travel

  • self guided

  • Luggage Transfers

CONTACT US Book now

ITINERARY

  • Day 1
  • Day 2
  • Day 3
  • Day 4
  • Day 5
  • Day 6
  • Day 7
  • Day 8
  • Day 9
  • Day 10
  • Day 11

DAY 1
Arrive in Volterra

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: Volterra

DAY 2
Walk to San Gimignano

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: San Gimignano

DAY 3
Loop Walk San Gimignano

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: San Gimignano

DAY 4
Walk to Colle Di Val D’Elsa

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: Colle Di Val D’Elsa

DAY 5
Transfer to Monteriggioni, walk to Siena

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: Siena

DAY 6
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: 317m
Meals included: Breakfast
Accommodation: Montalcino

DAY 7
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: Bagno Vignoni

DAY 8
Walk to Pienza

Begin the day with a rewarding stretch 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: 15km
Ascent: 400m
Descent: 250m
Meals included: Breakfast
Accommodation: Pienza

DAY 9
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 seeing the sunset over the Val d’Orcia.

Walk: 15km
Ascent: 550m
Descent: 450m
Meals included: Breakfast
Accommodation: Montepulciano

DAY 10
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: Montepulciano

DAY 11
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

  • 3 & 4 star

  • walking app

  • with ensuites

  • pack free

  • 10 nights ensuite room accommodation in Guesthouses, 3* & 4* Hotels
  • All luggage transfers and all taxi transfers as described in the itinerary
  • Option to upgrade to a wine resort in Gaiole in Chianti
  • 10 breakfasts and 1 dinner
  • Maps, daily walk notes, information pack and walking app
  • 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. 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 10 breakfasts and 1 dinner.  Lunches are available at various cafes or food stores daily. There are numerous places to get dinner each night, your hosts will give you a list of recommendations. If you have any food allergies or intolerances, please let us know at the time of booking so we can let your hosts know. Should you have severe food allergies, it’s always worth bringing a few of your own snacks with you.

  • NIGHT 1

  • NIGHT 2 & 3

  • NIGHT 4

  • NIGHT 5

  • NIGHT 6

  • NIGHT 7

  • NIGHT 8

  • NIGHT 9 & 10

FITNESS GUIDE

It’s well worth investing some time and effort preparing for your walking holiday. The graph shows the average daily distance, elevation and terrain difficulty for your hike. The dotted line indicates the average across all our walks, which will give you a feel for how challenging your walk is compared to all – and the recommended type, and amount, of preparation needed.  Of course, you can adapt this according to your existing fitness levels and lifestyle.

The graph and the information below can be used in conjunction with the fitness guide to help you prepare for your walking adventure. Across all of our walks, the average daily distance is 16.8km, the average daily elevation is 448m, and the average terrain difficulty is 5/10.

ngraph

DISTANCE - AVERAGE

Distance training is a major consideration in your overall training program. As you progress, incorporate longer walks into your training plan. Schedule one or two long walks each week, gradually increasing the distance until you can comfortably cover 17-25 km daily. Additionally, also include back-to-back walks to simulate walking on consecutive days. This helps your body adapt to the demands of walking for multiple days in a row. Take every opportunity you can to walk. If you have a fitness watch or phone, you should try to reach >15,000 steps every day. Ensure you can comfortably walk the average distance per day displayed in the graph, at least one month before you undertake your hike.

ELEVATION - AVERAGE

Elevation training is undoubtedly a consideration in your overall training program. Try to include some form of elevation in more than 40% of your walking and prioritise resistance training, whilst incorporating stairs anytime you can. Walking up and down stairs at work, at a local oval with a grandstand or up and down small hills, boring as that sounds, is incredibly useful. Elevation is often the chief walking killer, not distance, as it uses an entirely different set of muscles. Ensure you can comfortably walk the average elevation per day displayed in the graph, at least one month before you undertake your hike.

FLAT AND VARIED UNEVEN TERRAIN

Whilst training for walking on flat and slightly uneven terrain, you should focus on building endurance and ensuring you can maintain a comfortable pace.

Start with regular walks on sidewalks, roads, or paved paths to get used to the surface. Maintain a proper posture and engage your core muscles to support your back, keeping a steady gait. Ensure that you have comfortable, supportive footwear with adequate cushioning. If endurance is important, consider incorporating low-impact cross-training activities like swimming or cycling into your routine.

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 walking more enjoyable, an exercise regime of 2 to 3 times a week is needed. Walks are generally along well-defined trails. You should be used to walking between 10km-19km per day with up to 500m of ascent and descent. The vast majority of trails and tracks are well defined and cover a variety of terrain. On any typical day, you will be walking on forest trails, gravel tracks, rolling farmland, through vineyards and into the villages and towns where you will stay. It is commonplace in Italy that there are no separate footpaths (even in the towns) which means you will often be walking on the road. Please always be mindful of all road users when doing so. For each of the walks, you will be provided with daily walk notes, a map and the GPX tracks in our walking app.

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 marks the beginning of the grape harvests, so you might be lucky enough to encounter a local festival or two. By October, the summer heat has retreated. The days are warm with evenings cooling off. It isn’t uncommon for Tuscany to experience thunderstorms during summer days, so you should always be prepared for a change of season during the day.

How to get there and away

This walk starts in Volterra and ends in Montepulciano. Volterra does not have an airport, but nearby Siena has excellent train links to Pisa, Florence, and Rome airports. We can arrange a private transfer for you from Siena, or you can use the public transport links to Volterra. Siena does not have an airport.

However, the nearest train stations are in Cecina and Pontedera. From these stations, you can take a bus to Volterra. There’s also a smaller train station at Saline di Volterra, which is connected to Cecina by bus.

Buses also run to Volterra from Florence, Siena, and San Gimignano, often requiring a change at Colle di Val d’Elsa or Pontedera.

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).

Onward Travel From Montepulciano

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.

Insurance

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.

MAP

DEPARTURE DATES

  • DATES
    AVAILABILITY
    PRICE
    PER PERSON
    Single Occupancy
    DETAILS
  • 1 Apr 2025 - 31 Oct 2025
    AVAILABLE
    from

    $3195

    SINGLE OCCUPANCY
    $1195

    Not available from 1st July – 22nd August

  • 1 Apr 2026 - 31 Oct 2026
    AVAILABLE
    from

    $3295

    SINGLE OCCUPANCY
    $1245

    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: 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 and explore Tuscany from Volterra via the medieval powerhouse of Siena and the hilltop town of San Gimignano. From Siena, hike across the UNESCO-protected Val d’Orcia region to the elegant hilltop town of Montepulciano. Follow sections of the ancient pilgrim’s path, via Francigena, deep into a landscape of soft rolling hills and avenues of towering cypress trees. Explore the 16th-century wine town of Montalcino, renowned for its precious Brunello wine and enjoy the Roman way of life, soaking in the hot springs of Bagno Vignoni.

This is a moderate graded ramble through chestnut groves, vineyards and across classic Tuscan landscapes. Visit the hilltop hamlets of Castelnuovo dell’Abate and Monticchiello, among many other stunning Tuscany villages.

Highlights

  • Walk from Volterra, via Sienna through Tuscany’s Val d’Orcia region, to Montepulciano
  • Hang out in the glorious ‘Piazza del Campo’ in Siena and in the hilltop town of San Gimignano
  • Sample the award-winning Brunello wines of Montalcino
  • Soak in the thermal baths of Bagno Vignoni
  • Visit medieval abbeys, hilltop towers and Romanesque churches
  • Explore the Renaissance town of Montepulciano
  • Spend each night in classic Tuscan townhouses or rural hotels

WALK OVERVIEW

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

Grade 3 – Moderate

Short, steep hill sections. Walks that are longer than 12km with varied terrain. A moderate active lifestyle and some walking experience is recommended.

PRICE FROM
$ 3195

per person twin/double share

SINGLE OCCUPANCY
$ 1195

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

  • 30+ years

  • eco travel

  • self guided

  • Luggage Transfers

CONTACT US Book now
Itinerary

ITINERARY

  • Day 1
  • Day 2
  • Day 3
  • Day 4
  • Day 5
  • Day 6
  • Day 7
  • Day 8
  • Day 9
  • Day 10
  • Day 11

DAY 1
Arrive in Volterra

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: Volterra

DAY 2
Walk to San Gimignano

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: San Gimignano

DAY 3
Loop Walk San Gimignano

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: San Gimignano

DAY 4
Walk to Colle Di Val D’Elsa

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: Colle Di Val D’Elsa

DAY 5
Transfer to Monteriggioni, walk to Siena

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: Siena

DAY 6
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: 317m
Meals included: Breakfast
Accommodation: Montalcino

DAY 7
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: Bagno Vignoni

DAY 8
Walk to Pienza

Begin the day with a rewarding stretch 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: 15km
Ascent: 400m
Descent: 250m
Meals included: Breakfast
Accommodation: Pienza

DAY 9
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 seeing the sunset over the Val d’Orcia.

Walk: 15km
Ascent: 550m
Descent: 450m
Meals included: Breakfast
Accommodation: Montepulciano

DAY 10
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: Montepulciano

DAY 11
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

  • 3 & 4 star

  • walking app

  • with ensuites

  • pack free

  • 10 nights ensuite room accommodation in Guesthouses, 3* & 4* Hotels
  • All luggage transfers and all taxi transfers as described in the itinerary
  • Option to upgrade to a wine resort in Gaiole in Chianti
  • 10 breakfasts and 1 dinner
  • Maps, daily walk notes, information pack and walking app
  • 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. 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 10 breakfasts and 1 dinner.  Lunches are available at various cafes or food stores daily. There are numerous places to get dinner each night, your hosts will give you a list of recommendations. If you have any food allergies or intolerances, please let us know at the time of booking so we can let your hosts know. Should you have severe food allergies, it’s always worth bringing a few of your own snacks with you.

  • NIGHT 1

  • NIGHT 2 & 3

  • NIGHT 4

  • NIGHT 5

  • NIGHT 6

  • NIGHT 7

  • NIGHT 8

  • NIGHT 9 & 10

Fitness Guide

FITNESS GUIDE

It’s well worth investing some time and effort preparing for your walking holiday. The graph shows the average daily distance, elevation and terrain difficulty for your hike. The dotted line indicates the average across all our walks, which will give you a feel for how challenging your walk is compared to all – and the recommended type, and amount, of preparation needed.  Of course, you can adapt this according to your existing fitness levels and lifestyle.

The graph and the information below can be used in conjunction with the fitness guide to help you prepare for your walking adventure. Across all of our walks, the average daily distance is 16.8km, the average daily elevation is 448m, and the average terrain difficulty is 5/10.

ngraph

DISTANCE - AVERAGE

Distance training is a major consideration in your overall training program. As you progress, incorporate longer walks into your training plan. Schedule one or two long walks each week, gradually increasing the distance until you can comfortably cover 17-25 km daily. Additionally, also include back-to-back walks to simulate walking on consecutive days. This helps your body adapt to the demands of walking for multiple days in a row. Take every opportunity you can to walk. If you have a fitness watch or phone, you should try to reach >15,000 steps every day. Ensure you can comfortably walk the average distance per day displayed in the graph, at least one month before you undertake your hike.

ELEVATION - AVERAGE

Elevation training is undoubtedly a consideration in your overall training program. Try to include some form of elevation in more than 40% of your walking and prioritise resistance training, whilst incorporating stairs anytime you can. Walking up and down stairs at work, at a local oval with a grandstand or up and down small hills, boring as that sounds, is incredibly useful. Elevation is often the chief walking killer, not distance, as it uses an entirely different set of muscles. Ensure you can comfortably walk the average elevation per day displayed in the graph, at least one month before you undertake your hike.

FLAT AND VARIED UNEVEN TERRAIN

Whilst training for walking on flat and slightly uneven terrain, you should focus on building endurance and ensuring you can maintain a comfortable pace.

Start with regular walks on sidewalks, roads, or paved paths to get used to the surface. Maintain a proper posture and engage your core muscles to support your back, keeping a steady gait. Ensure that you have comfortable, supportive footwear with adequate cushioning. If endurance is important, consider incorporating low-impact cross-training activities like swimming or cycling into your routine.

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 walking more enjoyable, an exercise regime of 2 to 3 times a week is needed. Walks are generally along well-defined trails. You should be used to walking between 10km-19km per day with up to 500m of ascent and descent. The vast majority of trails and tracks are well defined and cover a variety of terrain. On any typical day, you will be walking on forest trails, gravel tracks, rolling farmland, through vineyards and into the villages and towns where you will stay. It is commonplace in Italy that there are no separate footpaths (even in the towns) which means you will often be walking on the road. Please always be mindful of all road users when doing so. For each of the walks, you will be provided with daily walk notes, a map and the GPX tracks in our walking app.

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 marks the beginning of the grape harvests, so you might be lucky enough to encounter a local festival or two. By October, the summer heat has retreated. The days are warm with evenings cooling off. It isn’t uncommon for Tuscany to experience thunderstorms during summer days, so you should always be prepared for a change of season during the day.

How to get there and away

This walk starts in Volterra and ends in Montepulciano. Volterra does not have an airport, but nearby Siena has excellent train links to Pisa, Florence, and Rome airports. We can arrange a private transfer for you from Siena, or you can use the public transport links to Volterra. Siena does not have an airport.

However, the nearest train stations are in Cecina and Pontedera. From these stations, you can take a bus to Volterra. There’s also a smaller train station at Saline di Volterra, which is connected to Cecina by bus.

Buses also run to Volterra from Florence, Siena, and San Gimignano, often requiring a change at Colle di Val d’Elsa or Pontedera.

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).

Onward Travel From Montepulciano

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.

Insurance

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.

Map

MAP

Departure Dates

DEPARTURE DATES

  • DATES
    AVAILABILITY
    PRICE
    PER PERSON
    Single Occupancy
    DETAILS
  • 1 Apr 2025 - 31 Oct 2025
    AVAILABLE
    Details
    from

    $3195

    SINGLE OCCUPANCY
    $1195
  • 1 Apr 2026 - 31 Oct 2026
    AVAILABLE
    Details
    from

    $3295

    SINGLE OCCUPANCY
    $1245
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: 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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