• 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
  • Hear a Gregorian chant in medieval abbey setting

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: Hotel Vecchia Oliviera

After our rendezvous we take a guided walking tour of Siena, undoubtedly one of Italy's most enchanting cities, and visit the wonderful cathedral and its stunning piazza. We take a scenic drive to Montalcino, in the heart of the Brunello wine country, for our Introductory Talk and Welcome Dinner.

Monday Overnight: Hotel Vecchia Oliviera

In the morning we explore the medieval treasures of Montalcino, one the most historic and vibrant Tuscan hilltop towns. After a short transfer we walk through olive groves and vineyards to the romantic abbey of SantAntimo to attend to a gregorian chant. After lunch in a local trattoria, we continue walking until we reach a family run Brunello organic wine farm where we will be shown the wine production in the canteens and enjoy a wonderful wine tasting.

Tuesday Overnight: Palazzo Del Capitano

We walk directly from the hotel over rolling hillsides, through vineyards and wheat fields, to the medieval village of San Quirico dOrcia, where we have lunch in a local restaurant. After lunch we walk through the countryside along dirt roads to the hot water Spa resort of Bagno Vignoni, with a Renaissance pool in the main square where hot water bubbles up from underground springs. Here Santa Caterina of Siena and Lorenzo the Magnificent, of the Medici family, came to enjoy the benefits of these waters. We can spend the afternoon in the hot water pool or wander around and relax in a café.

Wednesday Overnight: Palazzo Del Capitano

On Monte Cetona, we walk through oak and maple woods to see the caves where Saint Francis lived and continue to lunch in Castiglioncello del Trinoro. Trails through beech woods lead us to the spectacular stately gardens of La Foce, originally designed by the English architect Cecil Pinsent, and once the home of Iris Origo. The harmony between buildings, garden and nature makes this an ideal example of Tuscany's architectural and cultural evolution in the 20th century.

Thursday Overnight: La Bandita Town House

We walk to Pienza through the rolling hills and grain fields so typical of the region. Upon arrival in Pienza, we have lunch in a lovely trattoria and then a free afternoon in lovely Pienza. There are a number of beautiful and historic buildings to visit in Pienza, The Cathedral, Museum and the Popes Palace or spend the afternoon strolling around exploring this classic example of Renaissance town planning. Shopping is also available or simply sit in a cafe with a glass of wine and enjoy the views of the Tuscan hills.

Friday Overnight: La Bandita Town House

We walk to Sandra in Il Casale, an organic farm which produces cheese. We visit the farm and have the chance to join in preparing Tuscan specialties in a cooking class followed by lunch in this glorious setting. Afterwards we continue to Montepulciano, a stunning little renaissance town perched on its hill of tufa and famous for its "vino nobile" red wine, which we try for ourselves. We return to Pienza for an aperitif and Farewell Dinner.


This morning The Wayfarers arrange your transfer to Chiusi station.
"It's much less touristic. You get out in the countryside and see the real life of the country"
Terrain: Rolling hills, meadow paths, village lanes.7-12 miles walking per day.


6 nights from
Double Occupancy
(Single Supplement $595.00)
Our Wayfarers friends Price is $4,080.00


From Jun 22 to Jun 28 (more dates)
Request booking
Arrival: Siena Rail Station
Departure: Chiusi Rail Station


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Classic Tuscany June 2014 Map

Hotels - Where we stay

Hotel Vecchia Oliviera

Hotel Vecchia Oliviera

The Hotel Vecchia Oliviera is a friendly, intimate hotel situated at the gates of Montalcino in a beautiful setting with breathtaking views across the Val d'Orcia. It was originally an old olive oil mill that as been carefully renovated and is located only five minutes' walk from the old town's shops, restaurants and historic buildings. Each bedroom is personalised with the name of a flower and is tastefully furnished, offering every comfort: TV, phone, fridge, air conditioning, hydromassage shower, safe and internet access. The swimming pool within the garden overlooks the stunning countryside and is a great place to enjoy a glass of wine in the evening.

Palazzo del Capitano

Palazzo del Capitano

Located at the peak of this ancient walled, hilltop town, the hotel is snuggled amongst a maze of buildings and yet also offers tranquil outside space in its lovely Garden of Eden. The charming bedrooms are furnished in typical Tuscan style characterized by warm colors with particular attention to detail. Each is equipped with satellite TV, radio, minibar, safe, phone, hairdryer, bathroom with crystal shower, air conditioning and heating. The restaurant guarantees the finest quality food featuring a variety of local dishes and Tuscan delicacies. The Cave of Venus Spa offers guests secluded corners for private Wellness and relaxation.

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.

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