Classic Tuscany
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Classic Tuscany


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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.

Walk Summary


28-SEP-14 - 04-OCT-14


7 days, 6 nights


Walk Rating: Moderate. Rolling hills, meadow paths, village lanes. 7-12 miles walking per day.


US$4195.00 per person double occupancy
(single supplement US$595.00)

Walk begins in Montalcino, with arrival at Siena Rail Station and ends in Pienza, with departure from Chiusi Rail Station.

Walk Itinerary


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.

Overnight: Montalcino


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 Sant’Antimo to hear 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.

Overnight: Montalcino


We walk directly from the hotel over rolling hillsides, through vineyards and wheat fields, to the medieval village of San Quirico d’Orcia, 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.

Overnight: Bagno Vignoni


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.

Overnight: Bagno Vignoni


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.

Overnight: Pienza


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 taste. We return to Pienza for an aperitif and Farewell Dinner. 

Overnight: Pienza


This morning The Wayfarers arrange your transfer to Chiusi station.

This itinerary represents a typical Walk. We prepare itineraries well in advance of the trip and therefore we reserve the right to make changes due to weather, local events or other circumstances - but always to improve the experience of our guests.


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Hotel Vecchia Oliviera - Sunday & Monday

Hotel Vecchia Oliviera

Porta Cerbaia
Angolo via Landi 1
53024 Montalcino

T: +39 (0)577 846028
F: +39 (0)577 846029
E: [email protected]

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 personalized 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.

La Bandita Town House - Thursday & Friday

La Bandita Town House

Corso Rossellini 111, Pienza

T: +39 333 404 6704
Mobile: +39 3939 355593
E: [email protected]

 "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."

This hotel list is a provided as an example. We may use different hotels of the same quality and style on specific trips. The Wayfarers will notify confirmed travelers of any changes to the hotels.

Photo Gallery

Walking the Tuscan trails. Village walking. On the trail. Morning mist. Hands on practice! Poppies Hill top town. Villa a Tolli The hills are alive! Cooking lesson - the tools of the trade. Guinea fowl. Biscotti Gnocci The menu Cooking Sign for Il Rigo Fields Vienyards Lesley & Jock - Walk Leader and Manager.

Travel Information

Before & After Your Walk:

  • Spend time in Florence, one of the world's most beautiful cities and an unrivalled center of art and culture
  • Enjoy dining in restaurants in the home of Tuscan cuisine and Chianti wine
  • Visit Pisa, crammed full of wonderful, historical monuments and buildings dating back many hundreds of years including its famous Leaning Tower


In general the climate in Tuscany is very mild Temperate. Average temperatures are around 74ºF (23°C) in May and October, and 80ºF (27°C) in September with peak day temperatures sometimes several degrees higher. You are likely to need a jacket or light sweater in the evenings. The coast and valleys are mainly dry and sunny in September but there may be some rain in hilly areas. In May and October rain is a little more widespread. We recommend you bring good quality, light rain protection in all months.

To see more Travel Information and a list of our recommended tips please register or sign in. Once you confirm a booking for this walk, as a registered website member, you will be able to access detailed Joining Instructions including exact arrival and departure points and times as part of the Travel Information.


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  1. Are there any hidden costs?
    Our Vacations do not include the cost of air or rail fares to and from the destination or tips for your walk leader and manager.
  2. How large are the Groups?
    Our maximum group size is 16, but groups average between 8-12 people.
  3. Will I feel welcome as a single traveler?
    Yes! Our walks are the perfect environment of comfortable camaraderie for the single traveler.
  4. Can you accommodate special diets?
  5. How physically fit do I have to be to do a Wayfarers Walk?
    If you are in good health and reasonably fit you will be comfortable participating in a walk.

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Founded in 1984, The Wayfarers have been blazing new trails and leading the world in walking vacation adventures. Visiting England, Europe, the United States and New Zealand, the Wayfarers delivers fresh itineraries a new way in experiencing places and cultures. Walking Tours, European Walking Vacations and British Isle Walking Vacations provide the staple diet to a truly memorable holiday