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A Taste of Tuscany Self-Guided Walking

Rating: 4.5
Rating: 4.5/5 Read 2 reviews

Activity Level

Easy & Moderate

See our Activity Level Guidelines to check if this holiday is right for you.

Activity

Walking & Trekking

Overview

Based in the town of Chianciano Terme, on this single-centre walking holiday you’ll experience archetypal Tuscany: stunning timeless landscapes, delicious rustic cuisine, friendly local people and, of course, interesting walking routes.

This is not just a walking holiday it is a full immersion into local Tuscan life, from a guided walk passing the local produce providers to wine-tasting and a chance to bathe in sulphur-rich healing waters. You’ll walk through ancient chestnut forests, vineyards and olive groves, passing lakes and freshwater ponds alive with the sounds of frog chorus. Visit medieval, Roman and Etruscan towns and villages, sample the Vino Nobile of Montepulciano, rich Pecorino cheese in Pienza or take a bath in Roman Bagno Vignoni.

Key Information

What's Included

  • All accommodation
  • All buffet breakfasts and 4-course evening meals
  • Management by local hotelier
  • Headwater App
  • Wine, olive oil and local produce tasting
  • One thermal spa entrance

5 days of Walking & Trekking

Terrain:

The walking routes follow a mixture of paths, quiet roads, gravel track and woodland trails.

Highlights

  • Fabulous insight into traditional Tuscan life: the food, the wine, the culture
  • Wonderfully varied walking, including the beautiful UNESCO Val d'Orcia
  • Delicious classic Tuscan cuisine 'km 0' cooking (all local food)
  • The wine and cheese towns of Montepulciano and Pienza
  • Warm and welcoming agriturismo (farmhouse accommodation) with a passionate owner - the best of Italian hospitality

Itinerary

A Taste of Tuscany Self-Guided Walking
  • First Destination: Chianciano Terme
  • Next Destination: Chianciano Terme
  • Meals included:Dinner
  • Meals included:Breakfast, Dinner
  • Meals included:Breakfast, Dinner
  • Meals included:Breakfast, Dinner
  • Meals included:Breakfast, Dinner
  • Meals included:Breakfast, Dinner
  • Meals included:Breakfast, Dinner
  • Meals included:Breakfast
  • First Destination: Chianciano Terme
  • Next Destination: Chianciano Terme

Arrive at the Agriturismo La Pietriccia and enjoy a stroll to the old town, before your evening briefing by the owner, Stefano, and the first of many home cooked dinners. (Staying at the Agriturismo La Pietriccia for 7 nights, Half Board)

  • Meals included:Dinner

Today’s walk takes you over the hills around la Pietriccia, with stunning views over Monte Marzolana and Chianciano Terme itself. The walk will finish in Chianciano’s medieval centre, from where you can make your way back to the hotel or spend more time exploring this ancient spa town.

  • Meals included:Breakfast, Dinner

As you descend into the Valdichiana, a mix of quiet lanes and gravel tracks provide perfect views of the vineyards and over to Monte Rufeno. Passing pretty farmhouses you make your way to the small town of Montallese, and from here you pick up the Sentiero della Bonifica, a long-distance path between Chiusi and Arezzo. This leads you to the charming Lake Chiusi, where you can enjoy the birdlife and perhaps lunch at the lakeside restaurant. You will be transferred back to the hotel.

  • Meals included:Breakfast, Dinner

A short transfer takes you to the charming village of Castiglioncello; once abandoned it is now restored with a hotel, a cafe and the interesting Etruscan burial site. From the village you follow a trail through the forest to pass wonderful viewpoints of the area, dropping down to Poggio Pietraporciana, a Nazi gun point in the war. Continuing through the Pietraporciana Nature Reserve you pass the Rifugio Pietraporciana, once owned by the Marchesa of Val d’Orcia, Iris Origo, who, during the war, cordoned off this area to create a neutral zone, which the allies, Nazis and partisans all obeyed. From here, a forest track takes you past a charming argiturismo before a trail along a dried up river alongside rocky cliffs and on to the outskirts of Chianchiano stopping at the Dopolavoro La Foce where an optional transfer back to the hotel awaits you. Alternative carry on walking along a narrow trail with wonderful views and past a model of an Etruscan farm, before arriving in Chianchiano Terme and a choice of following the white gravel roads passing farms or through the town to return to the agriturismo.

  • Meals included:Breakfast, Dinner

Today you have time to yourself, maybe walk into Chianciano Vecchia and visit the Etruscan Museum of Chianciano Terme, enjoy olive oil tasting at the agriturismo or use your voucher for the Thermal Spa and relax in the healing waters or treat yourself to one of their many treatments.

  • Meals included:Breakfast, Dinner

Today you walk to the wine town of Montepulciano, where you will be rewarded with stunning views across the Valdichiana. Follow a chestnut-laden track to meet the forest road, before following a track around the vines and farmlands up to Montepulciano. You will be picked up here, but before this, take time to explore the town, which is full of wine bars and shops and has plenty of tasting opportunities.

  • Meals included:Breakfast, Dinner

After a short transfer to Pienza, take time to explore the town, it is one of the cheese capitals of Italy, and a beautiful mediaeval historic centre. Perhaps pick up a sandwich filled with porchetta or a slab of rich and creamy pecorino cheese. The walk takes you downhill from Pienza, crossing the stunning Val d’Orcia. It is an easy walk following a well-marked trail, giving you the chance to take in the views of mediaeval towns, rolling hills and rows of cypress trees. You will reach Bagno Vignoni then follow the river Orcia before climbing up to the town passing the spring baths and the old mill, before arriving in the Roman town, with its large baths in the centre of town. Perhaps treat yourself to the hot waters of the Hotel Posta Marcucci, where the baths come with a view! We transfer you back to the hotel for your final night of Stefano’s lovely food.

  • Meals included:Breakfast, Dinner

Leave Chianciano Terme

  • Meals included:Breakfast

Dates & Prices

A Taste of Tuscany Self-Guided Walking

Skip the hassle: We’ll handle your trip from start to finish, with competitive flight prices, dates that suit you, 24-hour support, loyalty discounts, and peace of mind for delays or disruption.

Read more about our flights
  • Saturday 28 Mar 2026 to Saturday 04 Apr 2026

    Availability
    Available

    This departure is available for new bookings, and will be guaranteed to go ahead once it reaches minimum numbers. Please click Continue to proceed with booking or contact our Sales team for assistance.

    Optional Single Supplement
    Free
    Available upon Request

    USD 2105 (excl. flights)

  • Saturday 04 Apr 2026 to Saturday 11 Apr 2026

    Availability
    Guaranteed (Available)

    This departure is available for new bookings and has reached the minimum number of passengers required to go ahead. Please click Continue to proceed with booking or contact our Sales team for assistance.

    Optional Single Supplement
    +USD 419
    Available upon Request

    USD 2105 (excl. flights)

  • Saturday 11 Apr 2026 to Saturday 18 Apr 2026

    Availability
    Available

    This departure is available for new bookings, and will be guaranteed to go ahead once it reaches minimum numbers. Please click Continue to proceed with booking or contact our Sales team for assistance.

    Optional Single Supplement
    +USD 419
    Available upon Request

    USD 2105 (excl. flights)

  • Saturday 18 Apr 2026 to Saturday 25 Apr 2026

    Availability
    Available

    This departure is available for new bookings, and will be guaranteed to go ahead once it reaches minimum numbers. Please click Continue to proceed with booking or contact our Sales team for assistance.

    Optional Single Supplement
    +USD 419
    Available upon Request

    USD 2105 (excl. flights)

  • Saturday 25 Apr 2026 to Saturday 02 May 2026

    Availability
    Guaranteed (On Request)

    This departure is guaranteed to go ahead and can be booked, although some components will need to be requested. Please click Continue to proceed with booking or contact our Sales team for assistance.

    Optional Single Supplement
    +USD 419
    Available upon Request

    USD 2105 (excl. flights)

  • Saturday 02 May 2026 to Saturday 09 May 2026

    Availability
    Guaranteed (On Request)

    This departure is guaranteed to go ahead and can be booked, although some components will need to be requested. Please click Continue to proceed with booking or contact our Sales team for assistance.

    Optional Single Supplement
    +USD 419
    Available upon Request

    USD 2300 (excl. flights)

  • Saturday 09 May 2026 to Saturday 16 May 2026

    Availability
    Guaranteed (On Request)

    This departure is guaranteed to go ahead and can be booked, although some components will need to be requested. Please click Continue to proceed with booking or contact our Sales team for assistance.

    Optional Single Supplement
    +USD 419
    Available upon Request

    USD 2300 (excl. flights)

  • Saturday 16 May 2026 to Saturday 23 May 2026

    Availability
    Available

    This departure is available for new bookings, and will be guaranteed to go ahead once it reaches minimum numbers. Please click Continue to proceed with booking or contact our Sales team for assistance.

    Optional Single Supplement
    +USD 419
    Available upon Request

    USD 2300 (excl. flights)

  • Saturday 23 May 2026 to Saturday 30 May 2026

    Availability
    Available

    This departure is available for new bookings, and will be guaranteed to go ahead once it reaches minimum numbers. Please click Continue to proceed with booking or contact our Sales team for assistance.

    Optional Single Supplement
    +USD 419
    Available upon Request

    USD 2300 (excl. flights)

  • Saturday 30 May 2026 to Saturday 06 Jun 2026

    Availability
    Guaranteed (Available)

    This departure is available for new bookings and has reached the minimum number of passengers required to go ahead. Please click Continue to proceed with booking or contact our Sales team for assistance.

    Optional Single Supplement
    +USD 419
    Available upon Request

    USD 2300 (excl. flights)

  • Saturday 06 Jun 2026 to Saturday 13 Jun 2026

    Availability
    Available

    This departure is available for new bookings, and will be guaranteed to go ahead once it reaches minimum numbers. Please click Continue to proceed with booking or contact our Sales team for assistance.

    Optional Single Supplement
    +USD 419
    Available upon Request

    USD 2300 (excl. flights)

  • Sunday 07 Jun 2026 to Sunday 14 Jun 2026

    Availability
    On Request

    This trip is available on request. Please proceed with your booking online or contact our Sales Team for assistance.

    Optional Single Supplement
    +USD 419
    Available upon Request

    USD 2340 (excl. flights)

  • Saturday 13 Jun 2026 to Saturday 20 Jun 2026

    Availability
    Available

    This departure is available for new bookings, and will be guaranteed to go ahead once it reaches minimum numbers. Please click Continue to proceed with booking or contact our Sales team for assistance.

    Optional Single Supplement
    +USD 419
    Available upon Request

    USD 2300 (excl. flights)

    Book with USD 575 deposit

  • Saturday 20 Jun 2026 to Saturday 27 Jun 2026

    Availability
    Available

    This departure is available for new bookings, and will be guaranteed to go ahead once it reaches minimum numbers. Please click Continue to proceed with booking or contact our Sales team for assistance.

    Optional Single Supplement
    +USD 419
    Available upon Request

    USD 2300 (excl. flights)

    Book with USD 575 deposit

  • Saturday 27 Jun 2026 to Saturday 04 Jul 2026

    Availability
    Available

    This departure is available for new bookings, and will be guaranteed to go ahead once it reaches minimum numbers. Please click Continue to proceed with booking or contact our Sales team for assistance.

    Optional Single Supplement
    +USD 419
    Available upon Request

    USD 2300 (excl. flights)

    Book with USD 575 deposit

  • Saturday 04 Jul 2026 to Saturday 11 Jul 2026

    Availability
    Available

    This departure is available for new bookings, and will be guaranteed to go ahead once it reaches minimum numbers. Please click Continue to proceed with booking or contact our Sales team for assistance.

    Optional Single Supplement
    +USD 419
    Available upon Request

    USD 2105 (excl. flights)

    Book with USD 526 deposit

  • Saturday 11 Jul 2026 to Saturday 18 Jul 2026

    Availability
    Available

    This departure is available for new bookings, and will be guaranteed to go ahead once it reaches minimum numbers. Please click Continue to proceed with booking or contact our Sales team for assistance.

    Optional Single Supplement
    +USD 419
    Available upon Request

    USD 2105 (excl. flights)

    Book with USD 526 deposit

  • Saturday 18 Jul 2026 to Saturday 25 Jul 2026

    Availability
    Available

    This departure is available for new bookings, and will be guaranteed to go ahead once it reaches minimum numbers. Please click Continue to proceed with booking or contact our Sales team for assistance.

    Optional Single Supplement
    +USD 419
    Available upon Request

    USD 2105 (excl. flights)

    Book with USD 526 deposit

  • Saturday 25 Jul 2026 to Saturday 01 Aug 2026

    Availability
    Available

    This departure is available for new bookings, and will be guaranteed to go ahead once it reaches minimum numbers. Please click Continue to proceed with booking or contact our Sales team for assistance.

    Optional Single Supplement
    +USD 419
    Available upon Request

    USD 2105 (excl. flights)

    Book with USD 526 deposit

  • Saturday 01 Aug 2026 to Saturday 08 Aug 2026

    Availability
    Available

    This departure is available for new bookings, and will be guaranteed to go ahead once it reaches minimum numbers. Please click Continue to proceed with booking or contact our Sales team for assistance.

    Optional Single Supplement
    +USD 419
    Available upon Request

    USD 2105 (excl. flights)

    Book with USD 526 deposit

  • Saturday 08 Aug 2026 to Saturday 15 Aug 2026

    Availability
    Available

    This departure is available for new bookings, and will be guaranteed to go ahead once it reaches minimum numbers. Please click Continue to proceed with booking or contact our Sales team for assistance.

    Optional Single Supplement
    +USD 419
    Available upon Request

    USD 2105 (excl. flights)

    Book with USD 526 deposit

  • Saturday 15 Aug 2026 to Saturday 22 Aug 2026

    Availability
    Available

    This departure is available for new bookings, and will be guaranteed to go ahead once it reaches minimum numbers. Please click Continue to proceed with booking or contact our Sales team for assistance.

    Optional Single Supplement
    +USD 419
    Available upon Request

    USD 2105 (excl. flights)

    Book with USD 526 deposit

  • Saturday 22 Aug 2026 to Saturday 29 Aug 2026

    Availability
    Available

    This departure is available for new bookings, and will be guaranteed to go ahead once it reaches minimum numbers. Please click Continue to proceed with booking or contact our Sales team for assistance.

    Optional Single Supplement
    +USD 419
    Available upon Request

    USD 2105 (excl. flights)

    Book with USD 526 deposit

  • Saturday 29 Aug 2026 to Saturday 05 Sep 2026

    Availability
    Available

    This departure is available for new bookings, and will be guaranteed to go ahead once it reaches minimum numbers. Please click Continue to proceed with booking or contact our Sales team for assistance.

    Optional Single Supplement
    +USD 419
    Available upon Request

    USD 2105 (excl. flights)

    Book with USD 526 deposit

  • Saturday 05 Sep 2026 to Saturday 12 Sep 2026

    Availability
    Available

    This departure is available for new bookings, and will be guaranteed to go ahead once it reaches minimum numbers. Please click Continue to proceed with booking or contact our Sales team for assistance.

    Optional Single Supplement
    +USD 419
    Available upon Request

    USD 2300 (excl. flights)

    Book with USD 575 deposit

  • Saturday 12 Sep 2026 to Saturday 19 Sep 2026

    Availability
    Guaranteed (Available)

    This departure is available for new bookings and has reached the minimum number of passengers required to go ahead. Please click Continue to proceed with booking or contact our Sales team for assistance.

    Optional Single Supplement
    +USD 419
    Available upon Request

    USD 2300 (excl. flights)

    Book with USD 575 deposit

  • Saturday 19 Sep 2026 to Saturday 26 Sep 2026

    Availability
    Available

    This departure is available for new bookings, and will be guaranteed to go ahead once it reaches minimum numbers. Please click Continue to proceed with booking or contact our Sales team for assistance.

    Optional Single Supplement
    +USD 419
    Available upon Request

    USD 2300 (excl. flights)

    Book with USD 575 deposit

  • Sunday 20 Sep 2026 to Sunday 27 Sep 2026

    Availability
    Guaranteed (On Request)

    This departure is guaranteed to go ahead and can be booked, although some components will need to be requested. Please click Continue to proceed with booking or contact our Sales team for assistance.

    Optional Single Supplement
    +USD 419
    Available upon Request

    USD 2300 (excl. flights)

    Book with USD 575 deposit

  • Saturday 26 Sep 2026 to Saturday 03 Oct 2026

    Availability
    Guaranteed (Available)

    This departure is available for new bookings and has reached the minimum number of passengers required to go ahead. Please click Continue to proceed with booking or contact our Sales team for assistance.

    Optional Single Supplement
    +USD 419
    Available upon Request

    USD 2300 (excl. flights)

    Book with USD 575 deposit

  • Saturday 03 Oct 2026 to Saturday 10 Oct 2026

    Availability
    Available

    This departure is available for new bookings, and will be guaranteed to go ahead once it reaches minimum numbers. Please click Continue to proceed with booking or contact our Sales team for assistance.

    Optional Single Supplement
    +USD 419
    Available upon Request

    USD 2300 (excl. flights)

    Book with USD 575 deposit

  • Saturday 10 Oct 2026 to Saturday 17 Oct 2026

    Availability
    Available

    This departure is available for new bookings, and will be guaranteed to go ahead once it reaches minimum numbers. Please click Continue to proceed with booking or contact our Sales team for assistance.

    Optional Single Supplement
    +USD 419
    Available upon Request

    USD 2300 (excl. flights)

    Book with USD 575 deposit

  • Saturday 17 Oct 2026 to Saturday 24 Oct 2026

    Availability
    Available

    This departure is available for new bookings, and will be guaranteed to go ahead once it reaches minimum numbers. Please click Continue to proceed with booking or contact our Sales team for assistance.

    Optional Single Supplement
    +USD 419
    Available upon Request

    USD 2300 (excl. flights)

    Book with USD 575 deposit

  • Saturday 27 Mar 2027 to Saturday 03 Apr 2027

    Availability
    On Request

    This trip is available on request. Please proceed with your booking online or contact our Sales Team for assistance.

    Optional Single Supplement
    +USD 419
    Available upon Request

    USD 2225 (excl. flights)

    Book with USD 556 deposit

  • Saturday 03 Apr 2027 to Saturday 10 Apr 2027

    Availability
    On Request

    This trip is available on request. Please proceed with your booking online or contact our Sales Team for assistance.

    Optional Single Supplement
    +USD 419
    Available upon Request

    USD 2225 (excl. flights)

    Book with USD 556 deposit

  • Saturday 10 Apr 2027 to Saturday 17 Apr 2027

    Availability
    On Request

    This trip is available on request. Please proceed with your booking online or contact our Sales Team for assistance.

    Optional Single Supplement
    +USD 419
    Available upon Request

    USD 2225 (excl. flights)

    Book with USD 556 deposit

  • Saturday 17 Apr 2027 to Saturday 24 Apr 2027

    Availability
    On Request

    This trip is available on request. Please proceed with your booking online or contact our Sales Team for assistance.

    Optional Single Supplement
    +USD 419
    Available upon Request

    USD 2225 (excl. flights)

    Book with USD 556 deposit

  • Saturday 24 Apr 2027 to Saturday 01 May 2027

    Availability
    On Request

    This trip is available on request. Please proceed with your booking online or contact our Sales Team for assistance.

    Optional Single Supplement
    +USD 419
    Available upon Request

    USD 2225 (excl. flights)

    Book with USD 556 deposit

  • Saturday 01 May 2027 to Saturday 08 May 2027

    Availability
    On Request

    This trip is available on request. Please proceed with your booking online or contact our Sales Team for assistance.

    Optional Single Supplement
    +USD 419
    Available upon Request

    USD 2435 (excl. flights)

    Book with USD 608 deposit

  • Saturday 08 May 2027 to Saturday 15 May 2027

    Availability
    On Request

    This trip is available on request. Please proceed with your booking online or contact our Sales Team for assistance.

    Optional Single Supplement
    +USD 419
    Available upon Request

    USD 2435 (excl. flights)

    Book with USD 608 deposit

  • Saturday 15 May 2027 to Saturday 22 May 2027

    Availability
    On Request

    This trip is available on request. Please proceed with your booking online or contact our Sales Team for assistance.

    Optional Single Supplement
    +USD 419
    Available upon Request

    USD 2435 (excl. flights)

    Book with USD 608 deposit

  • Saturday 22 May 2027 to Saturday 29 May 2027

    Availability
    On Request

    This trip is available on request. Please proceed with your booking online or contact our Sales Team for assistance.

    Optional Single Supplement
    +USD 419
    Available upon Request

    USD 2435 (excl. flights)

    Book with USD 608 deposit

  • Saturday 29 May 2027 to Saturday 05 Jun 2027

    Availability
    On Request

    This trip is available on request. Please proceed with your booking online or contact our Sales Team for assistance.

    Optional Single Supplement
    +USD 419
    Available upon Request

    USD 2435 (excl. flights)

    Book with USD 608 deposit

  • Saturday 05 Jun 2027 to Saturday 12 Jun 2027

    Availability
    On Request

    This trip is available on request. Please proceed with your booking online or contact our Sales Team for assistance.

    Optional Single Supplement
    +USD 419
    Available upon Request

    USD 2435 (excl. flights)

    Book with USD 608 deposit

  • Saturday 12 Jun 2027 to Saturday 19 Jun 2027

    Availability
    On Request

    This trip is available on request. Please proceed with your booking online or contact our Sales Team for assistance.

    Optional Single Supplement
    +USD 419
    Available upon Request

    USD 2435 (excl. flights)

    Book with USD 608 deposit

  • Saturday 19 Jun 2027 to Saturday 26 Jun 2027

    Availability
    On Request

    This trip is available on request. Please proceed with your booking online or contact our Sales Team for assistance.

    Optional Single Supplement
    +USD 419
    Available upon Request

    USD 2435 (excl. flights)

    Book with USD 608 deposit

  • Saturday 26 Jun 2027 to Saturday 03 Jul 2027

    Availability
    On Request

    This trip is available on request. Please proceed with your booking online or contact our Sales Team for assistance.

    Optional Single Supplement
    +USD 419
    Available upon Request

    USD 2435 (excl. flights)

    Book with USD 608 deposit

  • Saturday 03 Jul 2027 to Saturday 10 Jul 2027

    Availability
    On Request

    This trip is available on request. Please proceed with your booking online or contact our Sales Team for assistance.

    Optional Single Supplement
    +USD 419
    Available upon Request

    USD 2225 (excl. flights)

    Book with USD 556 deposit

  • Saturday 10 Jul 2027 to Saturday 17 Jul 2027

    Availability
    On Request

    This trip is available on request. Please proceed with your booking online or contact our Sales Team for assistance.

    Optional Single Supplement
    +USD 419
    Available upon Request

    USD 2225 (excl. flights)

    Book with USD 556 deposit

  • Saturday 17 Jul 2027 to Saturday 24 Jul 2027

    Availability
    On Request

    This trip is available on request. Please proceed with your booking online or contact our Sales Team for assistance.

    Optional Single Supplement
    +USD 419
    Available upon Request

    USD 2225 (excl. flights)

    Book with USD 556 deposit

  • Saturday 24 Jul 2027 to Saturday 31 Jul 2027

    Availability
    On Request

    This trip is available on request. Please proceed with your booking online or contact our Sales Team for assistance.

    Optional Single Supplement
    +USD 419
    Available upon Request

    USD 2225 (excl. flights)

    Book with USD 556 deposit

  • Saturday 31 Jul 2027 to Saturday 07 Aug 2027

    Availability
    On Request

    This trip is available on request. Please proceed with your booking online or contact our Sales Team for assistance.

    Optional Single Supplement
    +USD 419
    Available upon Request

    USD 2225 (excl. flights)

    Book with USD 556 deposit

  • Saturday 07 Aug 2027 to Saturday 14 Aug 2027

    Availability
    On Request

    This trip is available on request. Please proceed with your booking online or contact our Sales Team for assistance.

    Optional Single Supplement
    +USD 419
    Available upon Request

    USD 2225 (excl. flights)

    Book with USD 556 deposit

  • Saturday 14 Aug 2027 to Saturday 21 Aug 2027

    Availability
    On Request

    This trip is available on request. Please proceed with your booking online or contact our Sales Team for assistance.

    Optional Single Supplement
    +USD 419
    Available upon Request

    USD 2225 (excl. flights)

    Book with USD 556 deposit

  • Saturday 21 Aug 2027 to Saturday 28 Aug 2027

    Availability
    On Request

    This trip is available on request. Please proceed with your booking online or contact our Sales Team for assistance.

    Optional Single Supplement
    +USD 419
    Available upon Request

    USD 2225 (excl. flights)

    Book with USD 556 deposit

  • Saturday 28 Aug 2027 to Saturday 04 Sep 2027

    Availability
    On Request

    This trip is available on request. Please proceed with your booking online or contact our Sales Team for assistance.

    Optional Single Supplement
    +USD 419
    Available upon Request

    USD 2225 (excl. flights)

    Book with USD 556 deposit

  • Saturday 04 Sep 2027 to Saturday 11 Sep 2027

    Availability
    On Request

    This trip is available on request. Please proceed with your booking online or contact our Sales Team for assistance.

    Optional Single Supplement
    +USD 419
    Available upon Request

    USD 2435 (excl. flights)

    Book with USD 608 deposit

  • Saturday 11 Sep 2027 to Saturday 18 Sep 2027

    Availability
    On Request

    This trip is available on request. Please proceed with your booking online or contact our Sales Team for assistance.

    Optional Single Supplement
    +USD 419
    Available upon Request

    USD 2435 (excl. flights)

    Book with USD 608 deposit

  • Saturday 18 Sep 2027 to Saturday 25 Sep 2027

    Availability
    On Request

    This trip is available on request. Please proceed with your booking online or contact our Sales Team for assistance.

    Optional Single Supplement
    +USD 419
    Available upon Request

    USD 2435 (excl. flights)

    Book with USD 608 deposit

  • Saturday 25 Sep 2027 to Saturday 02 Oct 2027

    Availability
    On Request

    This trip is available on request. Please proceed with your booking online or contact our Sales Team for assistance.

    Optional Single Supplement
    +USD 419
    Available upon Request

    USD 2435 (excl. flights)

    Book with USD 608 deposit

  • Saturday 02 Oct 2027 to Saturday 09 Oct 2027

    Availability
    On Request

    This trip is available on request. Please proceed with your booking online or contact our Sales Team for assistance.

    Optional Single Supplement
    +USD 419
    Available upon Request

    USD 2435 (excl. flights)

    Book with USD 608 deposit

  • Saturday 09 Oct 2027 to Saturday 16 Oct 2027

    Availability
    On Request

    This trip is available on request. Please proceed with your booking online or contact our Sales Team for assistance.

    Optional Single Supplement
    +USD 419
    Available upon Request

    USD 2435 (excl. flights)

    Book with USD 608 deposit

  • Saturday 16 Oct 2027 to Saturday 23 Oct 2027

    Availability
    On Request

    This trip is available on request. Please proceed with your booking online or contact our Sales Team for assistance.

    Optional Single Supplement
    +USD 419
    Available upon Request

    USD 2435 (excl. flights)

    Book with USD 608 deposit

Your Group, Your Adventure

Want to choose your travel companions? Gather your family and friends and let us create a Private Adventure just for you.

View Details

Accommodation

A Taste of Tuscany Self-Guided Walking

Hotel

Your base for the week is the modest but comfortable Agriturismo La Pietricca, which stands on a hill with great views of Chianciano Vecchia. Stefano who runs the agriturismo will welcome you with his enthusiasm for everything to do with nature in the surrounding area and will also teach you all about the artisan products in the local area. The hotel produces 65% of what it serves on your table, and is surrounded by its own farm and orchards. There is a lovely terrace and swimming pool and lovely shady grassy area that looks out across the valley, where in the heat of summer you can take your dinner outside.

Essential Information

This is a self-guided tour; you can walk at your own pace (we recommend taking your time and enjoying the sights!)
Terrain & route: The walking routes follow a mixture of paths, quiet roads, gravel track and woodland trails.
Vehicle Support: This is a self-guided trip for those who prefer to walk independently, but with our assistance to take out the stress of the logistics and planning. We arrange your accommodation and provide you with route notes so that you can walk at your own pace. The hotelier, Stefano, will be there to meet you and will be available, throughout the trip, should you need assistance.

As this is a self-guided holiday there is no group and no leader. There may be others on the same departure date as you, but you will not be organised together. The route notes contain an emergency assistance telephone number should you need it and in emergencies, the hotelier will be able to help arrange a taxi or pick you up themselves. They may wish to charge for this service.

Alternative Air Travel
Alternative flights, onward rail to your holiday area, and connecting private transfers can be arranged from most UK airports.  We can also book UK shuttles to connect with your onward flight, please call for details and prices.

Alternative transfers
If you require alternative transfers, then we can usually arrange these for you (there may be an additional charge).

Self Drive
We can arrange various channel crossings for you. Please call for details and prices.

 

Italy

Travellers from the UK, US and EU normally do not need a visa to enter Italy. Please note, visa requirements often change and it is your responsibility to obtain any required visas for this trip. Therefore, we recommend that you check with the nearest embassy or consulate of your chosen destination(s), including any countries you may be transiting or transferring through.

Some local governments provide guidance on what visas their citizens need. To help, we’ve gathered a selection of useful links below.

• Australia: www.smartraveller.gov.au/destinations/europe/italy
• Canada: www.travel.gc.ca/destinations/italy
• United Kingdom: www.gov.uk/foreign-travel-advice/italy/entry-requirements
• USA:  www.travel.state.gov/content/travel/en/international-travel/International-Travel-Country-Information-Pages/Italy.html

Please note: it is compulsory to carry ID with you at all times in Italy.

Tuscan food is based on the Italian idea of ‘cucina povera’ (poor cooking); simple inexpensive meals that can be made for large groups. Whilst this was once dictated by the economy and expense of the produce, the tradition has remained. The cuisine of this region doesn’t use complicated seasonings or elaborate recipes, and instead focuses on fresh, high quality ingredients that allow the natural flavours in each dish to shine through. Typical dishes include fagioli con salsiccia (cannellini beans with sausage), tagliatelle al tartufo (pasta in a truffle sauce), bistecca alla Fiorentina (a T-bone steak which is only cooked blue/rare and often large enough to share!), pici (a fat, handmade spaghetti, often served with tomato and garlic sauce or game meat). Don’t miss the local cacio and pecorino cheeses and sample the famous wines: Nobile di Montepulciano and Brunello di Montalcino.

April and May departures can expect warm days, although rain is always possible. Nights may still be rather cool. Early June is similar, with the days becoming progressively hotter and the evenings much warmer. September and October are cooler and wetter, yet visibility is usually better. We strongly recommend a fleece-lined jacket or warm sweater in May, September and October.

As a certified B Corp, we’re on a mission to improve our social and environmental impact across all our adventures.

We do this through our innovative Thriving Nature, Thriving People plan.

This ‘nature positive’ approach is designed to help nature and communities thrive in harmony through practical solutions, such as reducing carbon and waste on our trips, supporting conservation projects through the Exodus Adventure Travels Foundation, and rewilding 100 square metres for every Exodus traveller.

Susan Hoogenboom

Rating: 5

A Taste of Tuscany- Self Guided Walking Tour

This tour was a welcome change from the fast paced touring of the big cities. We became familiar with the topography and vegetation as we hiked daily, also visiting towns known for wines and cheeses. The town of Chianciano provided a magnificent backdrop to our accomodation of Agriturismo La Pietriccia....

Most Inspirational Moment

The topography and vegetation of the Val d'Orcia. I fell in love with the cypress trees. The famous winding road lined with cypress. The history of the Etruscans, and learning of Iris Origo's recounting of the war in Val d'Orcia.

Thoughts on Group Leader

Stefano was available, knowledgeable and very personable!

Advice for Potential Travellers

There is a lot of walking, you need good walking shoes, a hat and insect repellent!

Suggestions

A great trip and a good balance to seeing the cities!

Barbara Dolynchuk

Rating: 4

HEADWATERS TUSCANY WALKABOUT

The walkabout was lovely. The agritourismo, food, wine and walking were great. The problem with the walkabout is namely directions. The directions submitted by Headwaters need to be updated. Sometimes, they just DID NOT WORK. This is very frustrating when you're in a country that you are unfamiliar with, are...

Most Inspirational Moment

The scenic views on the walks.....so astounding!!!!

Thoughts on Group Leader

Stephano was fabulous. He is a very thorough and conscientious guy. Even with the language barrier, Stephano was easily able to make his directions or point of what he was discussing clear. He was ALWAYS on time for transfers etc and very easy to chat with from destination to destination.

Advice for Potential Travellers

To do the walks you must be minimally in average shape/conditioning. Some of the hikes are easy but some (especially one) is quite steep and quite physically demanding!! Overall, Tuscany is very hilly so there is no getting around climbing!!

Suggestions

Overall, a trip of my lifetime. I enjoyed it very much. The 4 course meals are fabulous....sometimes too much. For example on one of the days we do a wine-tasting around 5 pm and then headed back to the Agritourismo for our 4 course meal. In retrospect, I would have asked the kitchen not to prepare a meal for me that evening because the wine-tasting we experienced was #1. fabulous #2. lots of meats, cheese and bread was provided to enjoy with the tasting. We were stuffed when we left.

USD 2105
8 Days Excluding Flights

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W07ST - A Taste of Tuscany Self-Guided Walking

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A Taste of Tuscany Self-Guided Walking