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’ll be warmly welcomed at the enchanting Agriturismo Il Rigo by our own 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
The opening walk of the trip is a delight that takes in one of the most iconic sights of the Val D’Orcia, namely the UNESCO World Heritage town of Pienza. Arriving in this exquisite medieval hill-top town in time for lunch gives you ample time to explore its historic and architectural treasures in the early afternoon, before marvelling at the rolling hills of the Val d’Orcia on the way home.
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
As Tuscany, and more importantly the Val d’Orcia, is home to some of the world’s best wines, join us for a complimentary winetasting 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 of the two walks today visits one the most iconic sights in Tuscany, the historic hamlet of Bagno Vignoni, famous for its hot springs. Sweeping valley views characterise 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 Francinega. 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 your 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 – famous for its stunning architecture, including the iconic fan shaped central square – the Piazza del Campo – and its towering Cathedral. No visit to Tuscany would be complete without a wander around its 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 four-course menu, often including home made fresh pasta. 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, another Tuscan gem, just after lunch.
Harder/Longer Option: 15.5 km, 4 – 6 hours walking, 530m ascent
A short complimentary transfer will take you to Pienza. Starting here, the harder walk today passes through the walled village of Montichiello, before passing through the vineyards that produce the famous Vino Nobile di Montepulciano red wine. The walk ends by passing the impressive San Biaggio Cathedral and then climbing up through the historic streets of Montepulciano. It’s 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 – as this is likely to depart at around 7am, in order to get guests to Pisa Airport in time for flights after 1200.