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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 pilgrim's path, via Francigena, deep into a landscape of soft rolling hills and avenues of towering cypress trees. Explore the 16th-century wine town of Montalcino, renowned for its precious Brunello wine and enjoy the Roman way of life, soaking in the hot springs of Bagno Vignoni.

Ramble through chestnut groves, vineyards and across classic Tuscan landscapes. Visit the hilltop hamlets of Castelnuovo dell'Abate and Monticchiello and if you're lucky, you may hear the mesmerizing Gregorian chants at the Abbey of Sant'Antimo. Finishing off with 2 nights in Montepulciano allows ample time to explore the charming streets and Renaissance architecture of Montepulciano.

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
  • 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
8 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
$ 1995

per person twin/double share

SINGLE OCCUPANCY
$ 715

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

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Departure Dates
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ITINERARY

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

DAY 1
Arrive in 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 the 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 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.

DAY 2
Walk to Monteroni d'Arbia

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 with 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: 317m
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 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 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: Hotel La Valle Piccolo
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 seeing the sunset over the Val d’Orcia.

Walk: 15km
Ascent: 550m
Descent: 450m
Meals included: Breakfast
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 and all taxi transfers as described in the itinerary
  • Option to upgrade to a wine resort in Gaiole in Chianti
  • 7 breakfasts 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. Of course, you can always call us too should you need anything during your walk. As many of the overnight stays are in small villages or towns, on occasion we may have to book another similar accommodation of equal standard. We will discuss these options with you during the booking process.

You will be provided with 7 breakfasts and 1 dinner.  Lunches are available at various cafes or food stores daily. There are numerous places to get dinner each night, your hosts will give you a list of recommendations. If you have any food allergies or intolerances, please let us know at the time of booking so we can let your hosts know. Should you have severe food allergies, it’s always worth bringing a few of your own snacks with you.

  • NIGHT 1

  • NIGHT 2

  • NIGHT 3

  • NIGHT 4

  • NIGHT 5

  • NIGHT 6 & 7

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 walks, average daily distance is 16.8km, average daily elevation is 448m, average terrain difficulty is 5/10.

ngraph

DISTANCE - ABOVE 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 in a single day. Also include walks on consecutive days to help 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 - ABOVE AVERAGE

Elevation training is a major consideration in your overall training program. You must include walks with serious hill climbs.

If you do not have access to hills, it is essential to replicate the elevation level you will be undertaking in any way possible such as on a treadmill or stair climber. Walking up and down stairs at work, at a local oval with a grandstand, or up and down small hills is incredibly useful. Also, prioritising resistance weight training will help you develop overall muscle strength.  Elevation is often where walkers encounter problems, opposed to distance, as it uses an entirely different set of muscles to everyday flat walking.

If high altitude is a factor, incorporate sessions at a higher altitude to acclimatise your body to reduced oxygen levels if you are able to. Ensure you can comfortably walk the average elevation per day displayed in the graph, at least one month before you undertake your hike.

TERRAIN

FLAT TERRAIN

Whilst training for walking on flat and hard 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.

MOUNTAINOUS / UNDULATING TERRAIN

As terrain associated with mountain climbs is often somewhat uneven and rocky, balancing and core exercises are vital.

Try to also include some form of elevation in more than 50% of your walking and prioritise resistance training, whilst incorporating stairs anytime you can. Walking up mountains or hills, up and down stairs at work, or up and down at a local oval with a grandstand is incredibly useful. Elevation is often where walkers encounter problems not distance, as it uses an entirely different set of muscles to everyday flat walking. Concentrate on doing lots of squats and lunges to build your glute muscles.

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 if you require to use them 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 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 Siena and ends in Montepulciano. There is no airport in Siena. However, you can drive or take a train or bus to Siena from other airports near Siena. Florence and Perugia are the closest airports to Siena and the larger airports of Pisa, Bologna and Rome generally offer a wider range of routes across Europe and beyond. Leaving Montepulciano is very easy to venture by train. Always remember to stamp your ticket before travel on either buses or trains!

Florence airport
You can travel by bus from Florence airport to Florence central. The bus service terminates in central Florence beside the main railway station of Santa Maria Novella. The journey is approximately 25mins. You can then choose to go to Siena by bus or by train. By bus the journey time is 1hr – 1hr 30mins.  There are two different bus lines that run between Florence and Siena. The RAPIDA or 131R is the fastest. It goes directly between the two cities on a dual carriageway. The DIRETTA stops at Poggibonsi and in Colle val D’Elsa – and can be handy if you would like to stop off and explore. By train the journey time via Empoli is 1hr 30mins.

Pisa Airport
From Pisa Airport you can take the ‘Pisa Mover’ train shuttle to the Pisa Centrale station to change for direct services to Siena. Journey time is 1hr-40mins. Please note You cannot buy tickets for the Pisa Mover in the main railway station. You have to walk down to the Pisa Mover itself where there are separate train ticket machines.

Rome Airport
Rome has two airports. Fiumicino and Ciampino. Whether you are travelling from Ciampino or From Fiumicino airports the best option is to head north and change at Chiusi-Chianciano Terme. From Ciampino Airport to Chiusi-Chianciano the journey is between 2hr 32min – 2hr 55 mins. From Flumicino Airport to Chiusi-Chianciano the journey is between 2hr 44min -3hr 55mins. From Chiusi-Chianciano the journey to Siena is 1hr 27min.

The other option is to take the fast train from Rome to Florence. Journey time is 1hr 36m and then connect with the train or bus for the next section of the trip.

Perugia Airport

From Perugia airport you can get a bus to Perugia Train Station. From here there are a few options. Firstly, you can take a bus. SAIS Autolinee have a bus service that takes around an 1 hr 30 mins. Secondly, you can go by train to Terontola, change and head for Chiusi, change again and go to Siena. Finally, you can choose to travel by train to Arezzo. The trip should take around 1hr. From Arezzo there is a bus service to Siena that will take around 1hr 20 mins.

Bologna Airport

From Bologna airport you can get a shuttle into Bologna’s Central Train Station and then a train to Florence. The Shuttle will take around 30 mins and the train to Florence will also take around 30 mins. From Florence you can choose to take the train or bus, as detailed above.

 

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

    $1995

    SINGLE OCCUPANCY
    $715

    Not available from 1st July – 22nd August

    BOOK NOW
  • 1 Apr 2026 - 31 Oct 2026
    AVAILABLE
    from

    $2095

    SINGLE OCCUPANCY
    $745

    Not available from 1st July – 22nd August

    BOOK NOW

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

Ramble through chestnut groves, vineyards and across classic Tuscan landscapes. Visit the hilltop hamlets of Castelnuovo dell'Abate and Monticchiello and if you're lucky, you may hear the mesmerizing Gregorian chants at the Abbey of Sant'Antimo. Finishing off with 2 nights in Montepulciano allows ample time to explore the charming streets and Renaissance architecture of Montepulciano.

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
  • 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
8 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
$ 1995

per person twin/double share

SINGLE OCCUPANCY
$ 715

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

DOWNLOAD PDF
Departure Dates
Book now
Itinerary

ITINERARY

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

DAY 1
Arrive in 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 the 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 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.

DAY 2
Walk to Monteroni d'Arbia

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 with 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: 317m
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 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 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: Hotel La Valle Piccolo
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 seeing the sunset over the Val d’Orcia.

Walk: 15km
Ascent: 550m
Descent: 450m
Meals included: Breakfast
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 and all taxi transfers as described in the itinerary
  • Option to upgrade to a wine resort in Gaiole in Chianti
  • 7 breakfasts 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. Of course, you can always call us too should you need anything during your walk. As many of the overnight stays are in small villages or towns, on occasion we may have to book another similar accommodation of equal standard. We will discuss these options with you during the booking process.

You will be provided with 7 breakfasts and 1 dinner.  Lunches are available at various cafes or food stores daily. There are numerous places to get dinner each night, your hosts will give you a list of recommendations. If you have any food allergies or intolerances, please let us know at the time of booking so we can let your hosts know. Should you have severe food allergies, it’s always worth bringing a few of your own snacks with you.

  • NIGHT 1

  • NIGHT 2

  • NIGHT 3

  • NIGHT 4

  • NIGHT 5

  • NIGHT 6 & 7

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 walks, average daily distance is 16.8km, average daily elevation is 448m, average terrain difficulty is 5/10.

ngraph

DISTANCE - ABOVE 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 in a single day. Also include walks on consecutive days to help 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 - ABOVE AVERAGE

Elevation training is a major consideration in your overall training program. You must include walks with serious hill climbs.

If you do not have access to hills, it is essential to replicate the elevation level you will be undertaking in any way possible such as on a treadmill or stair climber. Walking up and down stairs at work, at a local oval with a grandstand, or up and down small hills is incredibly useful. Also, prioritising resistance weight training will help you develop overall muscle strength.  Elevation is often where walkers encounter problems, opposed to distance, as it uses an entirely different set of muscles to everyday flat walking.

If high altitude is a factor, incorporate sessions at a higher altitude to acclimatise your body to reduced oxygen levels if you are able to. Ensure you can comfortably walk the average elevation per day displayed in the graph, at least one month before you undertake your hike.

TERRAIN

FLAT TERRAIN

Whilst training for walking on flat and hard 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.

MOUNTAINOUS / UNDULATING TERRAIN

As terrain associated with mountain climbs is often somewhat uneven and rocky, balancing and core exercises are vital.

Try to also include some form of elevation in more than 50% of your walking and prioritise resistance training, whilst incorporating stairs anytime you can. Walking up mountains or hills, up and down stairs at work, or up and down at a local oval with a grandstand is incredibly useful. Elevation is often where walkers encounter problems not distance, as it uses an entirely different set of muscles to everyday flat walking. Concentrate on doing lots of squats and lunges to build your glute muscles.

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 if you require to use them 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 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 Siena and ends in Montepulciano. There is no airport in Siena. However, you can drive or take a train or bus to Siena from other airports near Siena. Florence and Perugia are the closest airports to Siena and the larger airports of Pisa, Bologna and Rome generally offer a wider range of routes across Europe and beyond. Leaving Montepulciano is very easy to venture by train. Always remember to stamp your ticket before travel on either buses or trains!

Florence airport
You can travel by bus from Florence airport to Florence central. The bus service terminates in central Florence beside the main railway station of Santa Maria Novella. The journey is approximately 25mins. You can then choose to go to Siena by bus or by train. By bus the journey time is 1hr – 1hr 30mins.  There are two different bus lines that run between Florence and Siena. The RAPIDA or 131R is the fastest. It goes directly between the two cities on a dual carriageway. The DIRETTA stops at Poggibonsi and in Colle val D’Elsa – and can be handy if you would like to stop off and explore. By train the journey time via Empoli is 1hr 30mins.

Pisa Airport
From Pisa Airport you can take the ‘Pisa Mover’ train shuttle to the Pisa Centrale station to change for direct services to Siena. Journey time is 1hr-40mins. Please note You cannot buy tickets for the Pisa Mover in the main railway station. You have to walk down to the Pisa Mover itself where there are separate train ticket machines.

Rome Airport
Rome has two airports. Fiumicino and Ciampino. Whether you are travelling from Ciampino or From Fiumicino airports the best option is to head north and change at Chiusi-Chianciano Terme. From Ciampino Airport to Chiusi-Chianciano the journey is between 2hr 32min – 2hr 55 mins. From Flumicino Airport to Chiusi-Chianciano the journey is between 2hr 44min -3hr 55mins. From Chiusi-Chianciano the journey to Siena is 1hr 27min.

The other option is to take the fast train from Rome to Florence. Journey time is 1hr 36m and then connect with the train or bus for the next section of the trip.

Perugia Airport

From Perugia airport you can get a bus to Perugia Train Station. From here there are a few options. Firstly, you can take a bus. SAIS Autolinee have a bus service that takes around an 1 hr 30 mins. Secondly, you can go by train to Terontola, change and head for Chiusi, change again and go to Siena. Finally, you can choose to travel by train to Arezzo. The trip should take around 1hr. From Arezzo there is a bus service to Siena that will take around 1hr 20 mins.

Bologna Airport

From Bologna airport you can get a shuttle into Bologna’s Central Train Station and then a train to Florence. The Shuttle will take around 30 mins and the train to Florence will also take around 30 mins. From Florence you can choose to take the train or bus, as detailed above.

 

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

    $1995

    SINGLE OCCUPANCY
    $715
    BOOK NOW
  • 1 Apr 2026 - 31 Oct 2026
    AVAILABLE
    Details
    from

    $2095

    SINGLE OCCUPANCY
    $745
    BOOK NOW
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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