• 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

Rendezvous at Chiusi train station. A short drive brings us to the medieval village of San Quirico dOrcia, one of the five ˜comune that make up the UNESCO world heritage site of the Val d'Orcia. Introductory Talk and Welcome Dinner.

Monday Overnight: Palazzo del Capitano

This morning we explore the village of San Quirico dOrcia 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 will walk through the 16th century Horti Leonini before setting off across the rolling countryside of the Val dOrcia to to il Rigo where we will roll up our sleeves and don aprons for a cookery lesson. After lunch we pass by the wheat fields made famous by the film the Gladiator to the village of Pienza, a jewel of Renaissance architecture. There will be free time to visit the village and shop before being transferred back to San Quirico.

Tuesday Overnight: Palazzo del Capitano

This morning we will walk out of San Quirico along white roads and woodland to the village of Bagno Vignoni, an ancient spa resort with hot water bubbling up from the ground. The mineral rich waters have been enjoyed since Etruscan and Roman times. After lunch we have time to relax in the hot springs of this unique spa hamlet before being transferred back to San Quirico.

Wednesday Overnight: Etruria Resort

On Monte Cetona we walk through oak and maple woods to visit the caves of Saint Francis then continue on to lunch in Castiglioncello del Trinoro a tiny hamlet set in a spectacular position. After lunch we will continue down through the nature reserve of Pietraporciana to visit La Foce gardens, originally designed by the English architect Cecil Pinsent. We transfer to Montepulciano and enjoy dinner in our new hotel.

Thursday Overnight: Etruria Resort

We wander through the winding streets of Montepulciano leading down to the Tempio di San Biagio, one of the masterpieces of the High Renaissance. Then we wend our way along the white dirt roads so typical of this area, accompanied by vineyards and fantastic views, over the valley to an ancient farmhouse for lunch. In the afternoon we drive back to Montepulciano and enjoy a guided visit at one of the most historic wine cellars in the town, Cantina deRicci, followed by a wine tasting. There will be free time to shop.

Friday Overnight: Etruria Resort

This morning there will be a short transfer before starting a relaxing bike ride on the historic Sentiero della Bonifica, taking us along the agricultural plains of the Val di Chiana valley, cycling alongside the Maestro canal to Foiano della Chiana. Here we will be transferred to Lucignano, a small village set in a spectacular position overlooking the Val di Chiana, it is one of the most extraordinary examples of medieval urbanism because of its elliptical plan with concentric rings. After lunch we will explore the village and visit the museum which is home to the Tree of Life, one of the most remarkable examples of gold work in Tuscany.


This morning we will drive to Arezzo, birthplace of the artist Giorgio Vasari, for a short guided visit including the famous fresco cycle of the True Cross and masterpiece by Piero della Francesca. There will be free time to visit the antique market, one of the most important in Italy, which winds its way around the historic streets and squares. Departure is from 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
Double Occupancy
(Single Supplement $595.00)
Our Wayfarers friends' Price is $4,270.00


From Sep 24 to Sep 30 (more dates)
Request booking
Arrival: Chiusi Rail Station
Departure: Arezzo Rail Station


Walk ClassicGarden Visit
Classic Tuscany September 2017 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