Tuscany and Umbria
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Tuscany and Umbria


Art ConnectionsWine RegionGourmet FoodHistorical ThemeModerate Walking

If Tuscany is a legend, Umbria is a little-known medieval fable, its green heart beating in the shadow of its more famous neighbor. Our Walk combines the Tuscan hills, vineyards and Renaissance cities with a journey through the bucolic landscapes and enchanting lakes of Umbria.

We traverse a romantic landscape of mountains, rolling hills and deep valleys; walking on white roads that dip between hilltop towns, or shady forest tracks.

We savor private tastings of Chianti and Sagrantino wine, olive oil and honey, explore the glories of Siena, Assisi and Orvieto, discover awe-inspiring frescoes and visit the hill-top treasures of Cortona and Montefalco.

Walk Summary


07-SEP-14 - 13-SEP-14


7 days, 6 nights


Walk Rating: Moderate. Steady walking on hills, vineyard trails and forest tracks. 6-8 miles walking per day.


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

Walk begins in Orvieto, with arrival at Orvieto Rail Station and ends in Siena, with departure from Siena Rail Station.

Walk Itinerary


We meet in Orvieto and take a short walk around this stunning Etruscan city, before driving to our hotel near Montefalco. In the evening, we meet for our Introductory Talk and Welcome Dinner.

Overnight: Montefalco, Villa Zuccari


This morning's walk takes us across gentle hills and through the vineyards where the Sagrantino wine is made. In Montefalco we visit an old olive mill and, after lunch in the ancient walled town of Bevagna, we visit medieval "botteghe" (craftsmen's studio-workshops). We end our day with a wine-tasting before dinner in the hotel.

Overnight: Montefalco, Villa Zuccari


From the top of Monte Subasio, we walk to glorious Assisi with incredible views of the valley below. After lunch, we have a guided tour of the elegant squares, architectural splendors and the Basilica of St. Francis. We leave enchanting Umbria and travel to the rich landscape of Tuscany.

Overnight: Cortona, Villa Marsili


Today is spent in and around elegant Cortona. We pass by 'Bramasole', the house made famous by Frances Mayes in 'Under the Tuscan Sun', and spend time exploring this enchanting hilltop town. After lunch, we walk to the hermitage of Celle di San Francesco with stunning views of the valley and the town in the distance. In the evening, we dine in a local restaurant.

Overnight: Cortona, Villa Marsili


We leave Cortona and head for the renowned Chianti Classico region, where we spend the day walking through vineyards where the famous wine is produced. We pass charming old farmhouses and ancient castles to reach our historic hotel, part of an ancient feudal hamlet.  Here in the cantine, an expert sommelier will give us a wine tasting of their own production of Chianti Classico. A splendid dinner will follow.

Overnight: Gaiole in Chianti, Castello di Spaltenna


We walk to the renowned Badia a Coltibuono, founded by the monks of Vallombrosa a thousand years ago. We savor the rich history of this Monastery with a private tour of the villa, featuring its 16th century frescos, cloister and ancient wine-aging cellars, and the beautiful gardens. This is followed by an expert-guided tasting of their olive oils before lunch under a pergola in their renowned restaurant. In the afternoon we walk back to Gaiole with time to enjoy the beautiful hotel's gardens, 2 swimming pools and spa.


Overnight: Gaiole in Chianti, Castello di Spaltenna


After Breakfast, we transfer to Siena for a brief walking visit, before we say 'arrivederci' at the rail-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 Villa Zuccari - Sunday & Monday

Hotel Villa Zuccari

Hotel Villa Zuccari
Localita San Luca,
06036 Montefalco

Tel: +39.0742.399.402
Fax: +39.0742.399.194
E: [email protected]
W: www.villazuccari.com

The Hotel Villa Zuccari, in the San Luca district of Montefalco, is a large country house. The building's oldest wing dates back to the late 16th century while the facade and the general layout date back to the 1800's.  All rooms have king sized beds and are equipped with the latest technologies: Air Conditioning, Internet, Satellite TV, Safe, Hair Dryer etc. There is also a laundry service available and a 24 hour bar. The restaurant offers a completely traditional menu, with seasonal and local ingredients, favoring the regional cuisine and home-made pasta.  The villa is surrounded by centuries-old trees and grounds that extend over an area of 40,000 square meters, where guests can enjoy the 20 x 10 meter deck-level overflow swimming pool.

Castello Do Spaltenna - Thursday & Friday

Castello Do Spaltenna

Loc. Pieve di Spaltenna
Via Di Spaltenna 13
53013 Gaiole in Chianti

Tel:  +(39) 0577 749483
Fax: +(39) 0577 749269
W: www.spaltenna.it

Offering wonderful comfort and views over the valley or the cloister, from the grassy terraces in front of the castle, guests can enjoy the calm of the countryside and beauty of the surrounding landscape. The inside of the Castle is comfortable, elegant and sophisticated with 30 rooms and 8 suites, all equipped with air conditioning, satellite TV and mini-bar, hairdryer and en-suite facilities.  Guests can also enjoy one of the two swimming pools.  Chef Fabrizio Borraccino is inspired by a cuisine linked to the territory to create and match unique dishes which change according to the season and are presented with a professional, attentive and friendly service.

Sauna, Turkish bath and gym, tennis court, billiard and wellness center, complete the list of possible leisure activities available at Spaltenna.
For horse-riding lovers it is possible to rent horses not far from Spaltenna; trekking and biking lovers will find endless options for routes around the castle. A golf club is also available at one-hour distance.

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

Local Produce On the trail Tuscan country paths Pretty towns and villages Garden plants Tuscan window box A good lunch Garden visit Garden visit Chianti cellars Chianti vines Photo opportunity Ancient stone walls Tuscan Villa Historical visit Tower Fountain guardian D1010033.JPG D1010014.JPG TYU1-11_LB_AM_0291.JPG TYU1-11_LB_AM_0262.JPG TYU1-11_LB_AM_0289.JPG TYU1-11_LB_AM_0297.JPG TYU1-11_LB_AM_0294.JPG Tuscan Countryside Veronica\'s paintings. On the trail. Beautiful views. Etruscan Lunch in Umbria. Freedom on Foot! Making new friends. The locals are friendly. Gentle hills. Snail\'s pace. Hotel Relais Vignale - Pool Autumn harvest Villa Pambuffetti, Montefalco

Travel Information

Before & After:

  • In Siena visit the Etruscan museum and the Libreria Piccolomini to see the Pinturicchio frescoes
  • Gubbio and Urbino, historic centers of art and architecture, are worthy of a day's visit and Perugia is a gem.
  • Be on the lookout for some beautiful linen (before, during or after the walk) available in this region
  • Relax on the shore of Lake Trasimeno and enjoy fish fresh from the lake.


In general the climate in Tuscany and Umbria is very mild Temperate with landlocked Umbria being one or two degrees warmer than the coastal regions. 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.

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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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The Wayfarers, another "Best Adventure Travel Companies on Earth" is committed to providing inspired options for the very best of travel on two feet. Freedom of spirit and a passion for adventure set the scene. We seek out expert local walk leaders and put the focus on exciting itineraries featuring diverse landscapes, gracious lodging and delicious regional cuisine. Affordable pricing covers all accommodations, ground transfers, meals on itineraries, wine with dinner, entry to specified museums and historic sites, lectures and events.