Tuscany – Short Breaks

Tuscany, Italy

Holiday overview




Self Guided




Jan - Dec


£ 370 pp


5 nights

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Walking holidays Tuscany: We offer two short breaks in Tuscany – one based in the Renaissance town of Pienza, the other starting in Le Marche, staying in an exceptional agriturismo and finishing in Sepolcro – full details below.


Tour 1:

Based in Pienza.


In B&B accommodation: £245 per person based on 2 people sharing.

Single supplement: £85.


In 3-star hotel: £300 per person.

Single supplement: £105.


In 4-star hotel: £370 per person.

Single supplement £125.


Tour 2:

Based in historic agriturismo in Badia Tedaldo, finishing in Sepolcro.


£335 per person.
Single supplement £45.



Tour 1:

  • Three nights B&B in one of three types of accommodation – see above. All rooms with private facilities.
  • 3 breakfasts.
  • Route notes and itineraries.


Tour 2:

  • Two nights in an excellent Agriturismo (double room with private bath).
  • Two breakfasts.
  • Two dinners, beverages included.
  • One cooking class.
  • A guided walk with truffle hunter and dog.
  • 1 short walk plus 2 full day walks (self guided).
  • Route notes and maps, restaurant and shopping suggestions.
  • Day 1 transfer from Arezzo to Agriturismo.
  • Day 2 transfer to the start of the walk ( Sasso di Simone).
  • Day 3 luggage transfer to Sansepolcro.


Not Included:

  • Getting to or from starting and finishing points.
  • Insurance.
  • Lunches or dinners (Tour 1), lunches (Tour 2).
  • Drinks.
  • Entrance fees.
  • Anything not mentioned in the programme.


When to Go:

Available all year.

Best times:

Tour 1 – April through June and September through October.

Tour 2 – April through October.

Tour 1:

A self-guided walking break amid the Tuscan rolling hills as portrayed in Renaissance paintings, a landscape with a deep blue sky, and golden ochres and lush greens. From the famous vineyards of Vino Nobile and Brunello to walled Medieval and Renaissance towns visiting superb churches and abbeys with comfortable accommodation and typical restaurants. Ideal as a short break or as an add-on to another holiday.


Day 1:

Arrive Pienza

Explore the old town. In 1459 Pope Pius II (a humanist philosopher) decided to rebuild his hometown (Corsignano) employing Il Rossellino as his architect to build it according to Renaissance ideals, to be called “Pienza” (from Pius). Your walking maps and route notes await you here.

Highlights of the day: Stunning views of the Orcia valley and an easy walk (approx 2 km) in the environs of the town.


Day 2:

Montepulciano – Pienza

Take a public bus to Montepulciano, a medieval walled town built on a limestone ridge and filled with Renaissance palaces and chuches; and famous for its ‘vino nobile’, which you can taste here. Then, an easy walk of about 14 km/9 miles through classic Tuscan countryside filled with cypress trees and gorgeous villages, including the walled village of Monticchiello. Overnight Pienza.


Day 3:

Pienza – Bagno Vignoni – S. Quirico

Another easy walk of 14 km over rolling hills and through the tranquil and often overlooked village of S. Quirico d’Orcia. Before reaching Bagno Vignoni you will see the small village of Vignoni Alto with its picturesque medieval citadel. Bagno Vignoni is noted for its Renassaince thermal baths, where you can take a relaxing dip. Return to Pienza by public bus for overnight.


Day 4:

End of tour after breakfast.

Local bus service to Siena or Chiusi Railway Station.


Tour 2:

From Montefeltro to Valtiberina following the Via Ariminensis pilgrim route, with cooking class. From the Appennines that separate the Tuscan Tiber Valley from the Marecchia valley following the ancient paths of the pilgrims heading to Rome crossing the rugged highlands of Montefeltro, dotted with castles and medieval hamlets. Start in Le Marche, cross into Tuscany coasting the slopes of the Sasso di Simone, an impressive limestone rock dominating meadows and beech tree forests. Descend into the Valtiberina Toscana, depicted by Piero della Francesca. You will stay at Il Casalone – not an ordinary Agriturismo, but one specializing in the organic cultivation of forest fruits and old crops, the result of the careful restoration of a medieval castle.


Day 1:

Arrive Arezzo, transfer to Badia Tedalda (50 mins.)

Once accommodated in the Agriturismo, you may enjoy doing a relaxing exploratory walk in the environs in the oak woods where the precious truffles are found.Day 2: Sasso di Simone – Badia TedaldaToday you’ll experience a stunning walk across the meadows and woods of the Sasso di Simore Natural Reserve. The Sasso di Simone and the smaller Simoncello are two stunning limestone rock formations raising from the clay ravines and the forests of the area. The Sasso di Simone has always been an inspiring site for its flat plateaulike summit and its vast views. Follow footpaths to the Marecchia river valley and to Badia Tedalda, dominating the valley.

Walk Details: Moderate – 20 km or 16km; rolling hike reaching the base of the Sasso then a gradual descent towards the valley and a final ascent to the village of Badia Tedalda. Hands on cooking class. Overnight Il Casalone.


Day 3:

Badia Tedalda – Sansepolcro

From the meadows of Badia you will reach the forested ridges of the Apennines through paths used by pilgrims, soldiers and saints like St. Francis you will gradually enter the scenic Tiber valley. The vista of the Upper Tiber Valley is lovely and the tasty “secrets” of the local wood such as truffles and mushrooms are a must here.

Walk Details: Moderate/Difficult – approx 18 km (paths, double tracks and gravel roads).


End of tour.


Extra nights available in Sepolcro or elsewhere in Tuscany.


In Sansepolcro there is a bus connection to Arezzo railway station, connections to Florence and Rome. Direct bus departures are also available to Rome and Florence.