• SELF-GUIDED
  • 8 DAYS
  • Moderate
PRICE FROM $ 1,190 per person
SINGLE SUPPLEMENT $ 450 per person

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

AT A GLANCE

TRIP LENGTH
8 DAYS
WALK GRADE
Moderate
PRICE FROM
$ 1190 per person twin/double share
SINGLE OCCUPANCY
$ 450 per person

ITINERARY

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
  • Flexible itinerary to suit your walking needs
  • Enjoy worry-free navigation with your comprehensive maps, route notes and guidebook

ACCOMMODATION & DINING DESKTOP

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.

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, both are very easy to reach by train.

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 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.

CONTACT

If you have any questions, feel free to ask one of our destination consultants. You can get in touch with us via our contact form or email us at info@Stroll.com

MAP

DEPARTURE DATES

  • DATES
    AVAILABILITY
    PRICE
    Single Occupancy
    Details
  • 4 Apr 2024 - 31 Oct 2024
    AVAILABLE

    from $ 1190

    SINGLE OCCUPANCY
    $ 450

    Not available from 1st July – 22nd August

  • 1 Apr 2025 - 31 Oct 2025
    AVAILABLE

    from $ 1240

    SINGLE OCCUPANCY
    $ 470

    Not available from 1st July – 22nd August

sections

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
Itinerary
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
  • Flexible itinerary to suit your walking needs
  • Enjoy worry-free navigation with your comprehensive maps, route notes and guidebook
Accommodation & Dining

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.

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, both are very easy to reach by train.

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 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.

CONTACT

If you have any questions, feel free to ask one of our destination consultants. You can get in touch with us via our contact form or email us at info@Stroll.com

Map
Departure Dates
  • DATES
    AVAILABILITY
    PRICE
    Single Occupancy
    DETAILS
  • Date
    4 Apr 2024 - 31 Oct 2024
    AVAILIBILITY
    AVAILABLE
    PRICE
    from $ 1190
    SINGLE OCCUPANCY
    $ 450
    DETAILS

    Not available from 1st July – 22nd August

  • Date
    1 Apr 2025 - 31 Oct 2025
    AVAILIBILITY
    AVAILABLE
    PRICE
    from $ 1240
    SINGLE OCCUPANCY
    $ 470
    DETAILS

    Not available from 1st July – 22nd August

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.

ENQUIRE NOW

If you’re looking for further information on any of our walking holidays please fill out the enquiry form and we’ll be in touch.
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