Tuscany Walking Holidays

Arrive in the Val d’Orcia, with its rolling wheatfields and luscious vineyards. You’ll stay in the heart of the Tuscan countryside, nestled between the villages of San Quirico and Pienza. On arrival, you are warmly welcomed at the enchanting Agriturismo Il Rigo by our Walks Team and your hosts, Matthias and Luisa, who own Il Rigo and the surrounding land.

Easier Option: 12.5 km, 3 – 5 hours walking, 310m ascent
This introductory walk is a delight, taking in one of the Val D’Orcia’s great treasures, the UNESCO World Heritage town of Pienza. Arriving in this exquisite medieval hill-top town in time for lunch gives you the afternoon to explore its labyrinth of quaint and historic gems, before wending your way home in glorious surroundings.
Harder/Longer Option: 14 km, 4 – 6 hours walking, 440m ascent
An early morning extension takes you via Capella Vitaleta and the ever-photogenic Podere Belvedere before reaching Pienza.
Evening Wine Tasting
The Val d’Orcia is home to some world-beating wines, so join us for a complimentary wine-tasting before dinner this evening.

Easier Option: 13.5 km, 4 – 5 hours walking, 340m ascent
On this option, you’ll walk through the olive groves and vineyards that surround San Quirico before reaching an old Medici stronghold in the hamlet of Vignoni Alto.
Harder/Longer Option: 18 km, 5 – 6 hours walking, 304m ascent
The longer walk visits a Tuscan icon, namely the historic hamlet of Bagno Vignoni, famous for its hot springs and Roman baths. Sweeping valley views add much charm to the walk back to Il Rigo in the early afternoon.

Moderate Walk: 15.5 km, 4 – 6hours walking, 510m ascent
This walk follows the renowned ancient pilgrimage trail, known as the Via Francigena. Your destination is magical Montalcino, surrounded by the Brunello vineyards that produce one of the most celebrated red wines in the world. Today, a short transfer (included) will collect you from Montalcino at the end of the day.

Your rest day is the perfect opportunity to either visit Siena (transport included), or book yourself onto a cookery class to remember….
Siena needs no introduction. Awe-inspiring architecture abounds, and it is easy to spend hours in its iconic fan-shaped central square, the Piazza del Campo, with its towering cathedral. No visit to Tuscany would be complete without a wander around Siena’s historic streets and vibrant Contrade neighbourhoods.
Lorenza (Luisa’s mother) is an award- winning chef who offers traditional Tuscan cookery classes from her family home in San Quirico d’Orcia. With her expert guidance you will prepare together a seasonal 4-course menu, including home-made fresh pasta. N.B. the maximum group size is 4. The class starts at 10.45 and costs €80 per person.

Easier Option: 11.5 km, 3 – 4 hours walking, 206m ascent
A charming walk through countryside so synonymous with Tuscany and the Val d’Orcia. Enjoy extended views to Montalcino and Montepulciano and also the northern Crete Senesei region.
Harder/Longer Option: 17 km, 5 – 7 hours walking, 351m ascent
The longer walk today extends the morning’s route to incorporate the iconic and much-photographed Cipressi, perhaps Tuscany’s best example of a ring of Cypress trees, all set against golden wheatfields.

Easier Option: 9.2 km, 3 – 4 hours walking, 320m ascent
Today a short complimentary transfer takes our more leisurely walkers to the exquisite village of Montichiello. From here today’s shorter walk approaches Montepulciano through the famous Vino Nobile vineyards before arriving in the hill-top town itself, another cultural and architectural giant of the region.
Harder/Longer Option: 15.5 km, 4 – 6 hours walking, 530m ascent
A short complimentary transfer will take you to Pienza. Venturing out from here, you pass through the walled village of Montichiello, before traversing the vineyards that produce the famous Vino Nobile di Montepulciano red wine. The walk ends by passing the impressive San Biaggio Cathedral, before you ascend the historic streets of Montepulciano, a fitting finale to a week of wonderful walks.

Onward independent travel or return to Pisa Airport or Siena on our scheduled airport transfer. Expect an early start at around 7am, as we endeavour to get guests to Pisa Airport in time for flights departing from 1200 onwards.