• Guided tours of Siena and Orvieto
  • Visit medieval studio workshops
  • Walk through the vineyards of Chianti Classico
  • Olive oil tasting at ancient monastery
  • Visit the Basilica of St Francis in Assisi, A UNESCO World Heritage Site
  • Special cooking class at Badia a Coltibuono

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.

Sunday Overnight: Hotel Villa Zuccari

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.

Monday Overnight: Hotel 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 dinner and wine tasting in a lovely restaurant in Montefalco.

Tuesday Overnight: Hotel San Michele

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.

Wednesday Overnight: Hotel San Michele

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.

Thursday Overnight: Castello Di Spaltenna

We leave Cortona and transfer to the renowned Chianti Classico Region. Here we walk to the charming Badia a Coltibuono, founded by the monks of Vallombrosa 1,000 years ago. We dine at the gourmet restaurant under a pergola. After lunch, we savor the rich history of this monastery with a private tour of the villa featuring, its 16th-century frescoes, cloister and ancient cellars, and the beautiful gardens. An expert guides us in a tasting of olive oils and honey before we reach our historic hotel, part of an ancient feudal hamlet.

Friday Overnight: Castello Di Spaltenna

We spend a magical morning at Badia a Coltibuono learning to cook an authentic Tuscan meal (four courses!) and having the chance to sample the estate's organic wines while enjoying the meal we prepared. In the afternoon there is time for shopping before we return to our hotel for our Farewell Dinner.


After breakfast, we transfer to Siena for a brief walking visit, before we say "arrivederci" at the rail-station.
The Walk Leader "was well-informed, enthusiastic, fun to be with, flexible. I loved the way he took us down little side-streets to show us things only he knew about"
Terrain: Steady walking on hills,vineyard trails and forest tracks. 6-8 miles walking per day.


6 nights from
US $4,620.00
Per person, Double occupancy
(Single Supplement US $595.00)
Our Wayfarers friends' Price is US $4,620.00


From Jun 4 to Jun 10 (more dates)
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Arrival: Orvieto Rail Station
Departure: Siena Rail Station
Tuscany & Umbria Girls Getaway June 2017 Map

Hotels - Where we stay

Hotel Villa Zuccari

Hotel Villa Zuccari

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, favouring 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 metres, where guests can enjoy the 20 x 10 metre deck-level overflow swimming pool.

Hotel San Michele

Hotel San Michele

Set in the historic, medieval center of old Cortona, Hotel San Michele is in a quiet location only a few minutes stroll from the main squares and best restaurants. The building is a beautiful and treasured part of the old town “ it was formerly the Baldelli Palace, built in the 15thcentury. Today, the rooms have been carefully restored and updated to provide comfortable and characterful accommodation.
Rooms are furnished in classic Tuscan style. They all have en-suite bathrooms plus air conditioning, free wi-fi, TV with satellite channels, hairdryers and fridges.
Breakfast is served buffet-style in a magnificent room with a ceiling of massive, carved beams, or outside in the shady courtyard. Homemade cakes and sweet dishes are the highlight of the menu. Italians traditionally enjoy these for breakfast alongside a cappuccino, or perhaps a strong and invigorating espresso. For those without a sweet tooth, there is also a full selection of savory items such as cereals, omelet, toast and boiled eggs, plus straight-up Americano coffee, tea, fruit juice and hot chocolate.

Castello Di Spaltenna

Castello Di Spaltenna

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 centre, 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.

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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
  • Full Day cooking class at Badia a Coltibuono