• 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 appreciate 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.

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Sunday Overnight: Castello di Velona

Meet in Florence mid-morning and transfer to Siena for a fascinating tour around the medieval town center followed by lunch. You'll want to explore our palatial spa hotel and enjoy the dramatic views across the Val d'Orcia before a wonderful Tuscan Welcome Dinner.

Monday Overnight: Castello di Velona

Our walk begins in Tepolini, following ancient chestnut trees and olive groves to the Castello di Potentino for lunch and a sampling of its award winning wine. After lunch we explore this remarkable property, then return to our hotel with time to enjoy its premier facilities and gardens before dinner.

Tuesday Overnight: Castello di Velona

Today we explore the hilltop village of Montalcino, renowned for its Brunello wines. We explore the village and its ancient medieval walls, then roll up our sleeves and don aprons for a cooking class with our good friend and chef, Rafaella, in her country home. We'll feast on the traditional recipes we help prepare. This afternoon we follow ancient footpaths to the quiet Romanesque Abbey of Sant'Antimo. If the timing is right, we'll witness the monks raising their voices in song.

Wednesday Overnight: Castello di Spaltenna

This morning we say farewell to the beautiful Val d'Orcia as we make our way into the Siena countryside. We start our walk in Montagnole Senese, from where we walk to Castello di Celsa, a 16th century castle overlooking the Rosia valley. We'll have lunch and admire the fine terraced Baroque garden. We continue our walk to Villa Cetinale before driving to our elegant hotel in the Chianti hills.

Thursday Overnight: Castello di Spaltenna

Today we walk from the hotel to Gaiole, then up through woodlands to 11th century Badia di Coltibuono, in English, Abbey of Good Harvest. We'll enjoy lunch and a guided visit of the abbey and gardens, then taste their excellent olive oil. Afterwards, a leisurely stroll along one of Tuscany's typical "white" roads leads back to our captivating castle home.

Friday Overnight: Castello di Spaltenna

Breath in the rolling Tuscan landscape as we walk on white roads and wooded trails. We'll enjoy lunch and a Chianti Classico wine tasting at Castello di Ama, followed by a visit to the winery. Enjoy some free time in Radda before transferring back to our wonderful hotel for a memorable Farewell Dinner.


The Wayfarers will transfer you after breakfast to the Hotel Minerva in Florence or Florence Train Station or Florence Airport.
Our visit to Castello di Potentino was unforgettable.
Ancient limestone footpaths over a rolling landscape with some walking in woodlands and vineyards. 5 - 9 miles of walking per day.


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


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Begins: Grand Hotel Minerva, Florence
Ends: Florence
Tuscan Gardens & Castles Map

Hotels - Where we stay

Castello di Velona

Castello di Velona

At first glance, the Castello di Velona Resort, (it is a hotel, thermal spa and winery) is a breathtaking sight, a renovated fortress dating to the 11th century, nestled on a hill overlooking with Val d'Orcia. It's hard to resist the 360-degree views of olive trees and vineyards that produce the world-famous Brunello wines of Montalcino. Guest rooms are decorated in traditional Tuscan style, many with exposed beams or vaulted ceilings. Each room features ensuite bath, air conditioning, private balcony, phone, TV, coffee station and minibar.
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