• 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

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.

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
Per Person, Double Occupancy
(Single Supplement $595.00)
Our Wayfarers friends Price is $4,270.00


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Arrival: Orvieto Rail Station
Departure: Siena Rail Station


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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