• 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 Brunello region
  • Cycle on the historic Sentiero della Bonifica

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: La Bandita Town House

Rendezvous at Chiusi train station. A short drive brings us to Pienza, a remarkable example of Renaissance town planning set on a hill with stunning views over the UNESCO world heritage site of the Val d'Orcia and Monte Amiata. After our Introductory Talk and Welcome Drink we will enjoy the first of our delicious Tuscan meals.

Monday Overnight: La Bandita Town House

This morning we will stroll the narrow vicoli of Pienza and visit the Romitorio, an Etruscan tomb carved out of the tufo rock and later used as a hermitage by monks from a nearby abbey. We will then take a scenic walk to a farmhouse for lunch. The afternoon walk will take us to Monticchiello, a charming medieval village which preserves its old paving, characteristic stone houses and hidden gardens. We will then drive back to Pienza in time for a siesta before another memorable dinner.

Tuesday Overnight: La Bandita Town House

This morning we will walk down below the ancient walls of Pienza and visit the Pieve of Corsignano, stunning in its simplicity. We will then cross the wheat fields made famous by the film 'Gladiator' to il Rigo where we will roll up our sleeves and don aprons for cookery lesson. After lunch we will continue on to Bagno Vignoni to relax in the hot water springs of this unique spa hamlet.

Wednesday Overnight: Villa Cicolina

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: Villa Cicolina

This morning we will walk through rolling countryside and vineyards below Montepulciano to visit Cantina Salcheto, a fascinating organic and biodynamic wine estate where we will visit the cellars and learn how they manage their wine production with maximum attention to being environmentally friendly. Here we will taste their wines over a lunch using local products and seasonal vegetables from their garden. After lunch we will be driven back to Montepulciano to explore the cellars of the wine cathedral dug out below the town.

Friday Overnight: Villa Cicolina

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 25 to Oct 1 (more dates)
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Arrival: Chiusi Rail Station
Departure: Arezzo Rail Station


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Classic Tuscany September 2016 Map

Hotels - Where we stay

La Bandita Town House

La Bandita Town House

La Bandita is a luxury boutique hotel in the historic center of Pienza. The building is a rambling Renaissance-era palazzo where nuns have lived for over 500 years. The nuns' cells have been replaced by 12 large guest rooms merging contemporary design with wood beam ceilings, parquet floors, and exposed, centuries-old stone walls. All rooms air-conditioning, hair dryer and free wi-fi access with safety deposit & irons available at reception. Behind the property is a private walled garden with shaded day-beds for lounging and a small plunge pool.

Villa Cicolina

Villa Cicolina

A former country residence of one of Montepulcianos noble families, the 16th century villa has been transformed into an elegant and airy hotel. Carefully restored by its owners, who love to travel, original features have been preserved to maintain the sense of history, while creating the ambience of African safari lodges where the environment blends with stylish and comfortable accommodation. Surrounded by lovely gardens and with an infinity pool and whirlpool bath, it is a haven of peace and tranquility offering stunning views of the Tuscan countryside. The individually designed suites feature an ensuite bath and shower, air-conditioning and heating, a hairdryer, satellite TV, telephone, safe, minibar and WiFi internet access. The cuisine on offer in Villa Cicolinas restaurant is inspired by the products of the region, using Tuscany's famous cured meats, beef, cheeses and vegetables and herbs grown in the kitchen garden and the Villas own olive oil.

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