• Visit Siena, Montalcino, Gaiole, and Radda in Chianti
  • Overnight in luxurious historic castles
  • Explore lovingly restored ancient estate gardens
  • Walk in lush landscapes of the Val d'Orcia and Chianti
  • Wine tastings of Brunello and Chianti Classico
  • Tuscan cooking class
  • Even those who have been to Tuscany countless times will enjoy the pure fun and indulgence of this wonderful adventure. We spend a week walking in Tuscany's beautiful Val d'Orcia and the Chianti Hills, stopping for wine tastings and visits to famous (and private) gardens, dining on fine local delicacies, and staying each night in a historic fairytale castle. Local lore and individual family stories have a huge part in our understanding of this place, going as far back as the Etruscans. Along the way, we meet vitners, farmers, chanting monks, a chef, a shepherd and so many others, all adding to care free pleasure of Wayfarers' world-class walking in a place such as this. Designed specially to apreciate Tuscany's lush countryside and rich bounty, this walk thoughtfully brings us closer to the art, history and agriculture for which Tuscany is famous and make it such a glorious place to be.

    Favorite aspect of the trip (testimonial)
    Ancient limestone footpaths over a rolling landscape with some walking in woodlands and vineyards.


    US $5,395.00
    Per Person, Double Occupancy
    (Single Supplement US $995.00)
    Our Wayfarers friends' Price is US $5,125.00


    From Sep 20 to Sep 26 (more dates)
    Request booking
    Begins: Grand Hotel Minerva, Florence
    Ends: Florence
    Tuscan Gardens & Castles September 2020 Map

    Hotels - Where we stay

    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