• Rolling landscapes, brilliant light and breathtaking medieval villages
  • San Quirico d'Orcia, Pienza, Montepulciano, Bagno Vignoni
  • Walk on an ancient pilgrims' route, visit the caves of St Francis
  • Wine 'cathedral' visit and wine tastings
  • Tuscan cooking class, thermal spa visit, La Foce gardens, cycling

The Italian Renaissance sprang from the rich landscape of Tuscany - its green and golden hills, groves of cypress and olive trees, brilliant light and exquisite cities. From this rich earth comes the acclaimed cuisine of Tuscany, one of the world's healthiest. Feast on olive oil, Tuscan beans, vegetables, fish, pasta, crostini, risotto, handmade cheeses, succulent beef and wild boar. Hearty, honest and subtle, the food, like the country, is a revelation.

We walk in a UNESCO World Heritage Site, explore the medieval treasures of Montalcino in the heart of the Brunello wine country, enjoy a wine tasting at an organic farm and delight in a lesson about Tuscan cooking.

Sunday Overnight: Palazzo del Capitano

Meet at Chiusi train station. A short drive brings us to medieval San Quirico d'Orcia, one of the five communes that make up the UNESCO World Heritage Site of the Val d'Orcia. Introductory Talk and Welcome Dinner tonight.

Monday Overnight: Palazzo del Capitano

Explore the village of San Quirico d'Orcia with its medieval walls. Set on the Via Francigena, an ancient pilgrims' route, it has seen the passage of popes, mercenaries, kings and emperors. We set off to il Rigo for a cookery lesson and lunch. Afterwards, we walk on to Pienza.

Tuesday Overnight: Palazzo del Capitano

Walk out of San Quirico along white roads and woodlands to Bagno Vignoni, an ancient spa resort where hot water bubbles up from the ground. The mineral-rich waters have been enjoyed since Etruscan times. After lunch, we have time to relax in the hot springs of this unique hamlet.

Wednesday Overnight: Villa Cicolina

Oak and maple woods lead the way for today's visit to the caves of Saint Francis. We'll stop for lunch at Castiglioncello del Trinoro, a tiny hamlet with heart-stopping views. Then descend through a nature reserve to visit La Foce gardens, originally designed by the English architect Cecil Pinsent.

Thursday Overnight: Villa Cicolina

This morning we walk through rolling countryside and vineyards towards Montepulciano. Along the way we stop at a charming farmhouse for lunch in the garden. Once in Montepulciano, we explore the cellars of the wine 'cathedral' dug out below the town and taste some of their wines.

Friday Overnight: Villa Cicolina

After a short transfer, walk on the hillsides of the Chiana valley. We'll lunch in the medieval village of Lucignano, a fine example of modern urban planning, with streets built into concentric rings and spectacular views overlooking the valley. We explore the village and museum, home to the exquisite  Tree of Life, a masterpiece of gold work.


Before we depart, one last visit to the birthplace of artist Giorgio Vasari in Arezzo, to see the famous fresco cycle of the True Cross by Piero della Francesca. Transfer to the rail station in Arezzo.
"It's much less touristic. You get out in the countryside and see the real life of the country."
Terrain: Unpaved roads, woodland trails with some hills 4-9 miles walking per day. 15 miles easy cycling on Friday.


6 nights from
US $4,495.00
per person, double occupancy
(Single Supplement US $695.00)
Our Wayfarers friends' Price is US $4,270.00


From Sep 29 to Oct 5 (more dates)
Request booking
Arrival: Chiusi-Chianciano Terme Rail Station
Departure: Arezzo Rail Station
Classic Tuscany September 2019 Map

Hotels - Where we stay

Palazzo del Capitano

Palazzo del Capitano

Set just inside the historic town walls of San Quirico, Palazzo del Capitano is a charming 15th-century building. The rooms are decorated in rustic style, with wooden-beamed ceilings, antique furniture and terracotta floors. They all have satellite TV, free Wi-Fi, radio, hairdryer, minibar air conditioning, heating, safe and en-suite bathrooms fitted with travertine marble. Guests can also enjoy the relaxing Zodiac Lounge. The hotel restaurant, 'Al Vecchio Forno', is housed in what were once the stables. This Michelin-recommended restaurant serves traditional Tuscan food and wine indoors by the fireplace, or outside under the olive trees, depending on the season and guests preferences. Palazzo del Capitano is surrounded by peaceful olive groves and features a wellness center and a garden with vegetable patches, flowers and fountains. The wellness center includes a hot tub, a Turkish bath and massage facilities (the wellness center needs to be pre-booked and entails an extra charge.)

Villa Poggiano

Villa Poggiano

Villa Poggiano is an elegant, fully restored 18th century villa, nestled in parkland just outside Montepulciano with panoramic views of the famous wine town and the soft hills of the Val dOrcia. The hotel suites and rooms are elegantly furnished with antique furniture, paintings and fittings, with spacious marble bathrooms fitted with showers or/and bathtubs. All rooms have satellite TV, strongbox, mini-bar, direct access to Internet and an external telephone line. Every morning, guests are treated to a display of delicious cakes, biscuits and pastries all made on premises. The Villa has a magnificent marble swimming pool decorated with statues and fountains.

Start planning your trip

What Is Included in the Price of My Vacation

  • Full-time services of two staff - a Walk Leader and Walk Manager
  • A backup vehicle for resting walkers and moving luggage
  • Comprehensive Travel Information Package and Reading List
  • Diverse itineraries with an emphasis on history, geography, culture, peoples, flora and fauna
  • Demonstrations, wine tasting, admissions to museums and historic sites
  • All ground transfers (ferries, cable cars, trains, etc.)
  • Maps and unique souvenirs to commemorate your trip
  • First-class accommodations with cultural and historical interest
  • All meals - with choices - (Special dietary requirements? No problem!)
  • Wine with dinner
  • On-trail snacks and refreshments
  • All gratuities at hotels and restaurants