• Rich landscape, brilliant light and exquisite villages
  • Learn how to prepare Tuscan farmhouse specialities
  • Visit the caves where St Francis lived
  • Organic wine tasting in renowned Montepulciano region
  • Cycle on the historic Sentiero della Bonifica
  • Relax in the hot springs

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: Etruria Resort

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: Etruria Resort

Follow the rolling countryside and vineyards below Montepulciano to visit Cantina Salcheto, a fascinating organic and biodynamic wine estate. We taste their wines over a lunch of local products and seasonal vegetables from the estate. After lunch, we drive back to Montepulciano to explore the cellars of the wine cathedral.

Friday Overnight: Etruria Resort

After a short transfer, take a relaxing bike ride on the historic Sentiero della Bonifica through the agricultural plains of the Val di Chiana valley, cycling alongside the Maestro canal to Foiano della Chiana. Transfer to Lucignano, a fortified medieval village, built into concentric rings with spectacular views. We explore the village and view the 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
per person, double occupancy
(Single Supplement $695.00)
Our Wayfarers friends' Price is $4,270.00


From May 27 to Jun 2 (more dates)
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Arrival: Chiusi Rail Station
Departure: Arezzo Rail Station


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Classic Tuscany 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.)

Etruria Resort

Etruria Resort

A charming hotel, once a noble gentlemans villa, built in 1800, it has been thoughtfully renovated to reflect its origins while providing all modern conveniences. Surrounded by extensive grounds, including a secret garden, with an outdoor pool and a spa providing a wide range of pampering treatments, the hotel is in the heart of the land of the vino nobile di Montepulciano. Elegant and comfortable rooms, each individually furnished and decorated, offer a hairdryer, WiFi, satellite TV, safe, minibar, telephone, heating and air-conditioning. The chefs in the La Corte di Bacco restaurant prepare the best of Tuscan cuisine using the famous local olive oil and produce.

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