Walks and wine

A Different Path
Under the Tuscan Sun

A walking journey through rural Tuscany, where conversations with winemakers, artists and families reveal another way of living

Creative culture
Inner reset
Slow living
Tuscany, Italy
Map View
Overview

Most of us spend our lives surrounded by people making similar choices. Yet every so often, we encounter someone whose story makes us stop and think differently. Set among the rolling landscapes, hilltop villages and ancient roads of Val d'Orcia, this journey follows a carefully curated route through one of Italy's most inspiring landscapes. Over shared meals, walks through the Tuscan countryside and unhurried conversations, the people who call Tuscany home gently invite you to consider a simple question: what else might be possible?

Tuscan walks 
Life among vines 
Artist's studio
Truffle hunt
Long table 
Farm-to-table
Local hospitality
Countryside sunsets
A Signature Journey
From £0
Tailored to you
No two journeys are exactly the same. Every experience is adapted around your interests, preferred pace, group size and travel dates.
Start your journey
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Begin
Leaving the familiar behind

In the Val d’Orcia, days unfold on foot, following vineyard tracks, cypress-lined lanes and ancient paths between hilltop villages. Each walk leads somewhere – a vineyard, a farmhouse, a studio, or simply another beautiful stretch of Tuscan countryside. A trusted guide takes care of the journeys in between, leaving you free to follow the path and see where it leads.

Purpose
Among the vines

At a small winery overlooking the Val d’Orcia, glasses are poured as you wander between the vines with the owner, talking about harvests, seasons and life shaped by the land. Over local cheeses, fresh bread and wines from the estate, hear how a corporate career was exchanged for vineyards, harvests and the chance to nurture a long-held passion.

Creativity
Choosing beauty

At a small studio, paintings lean against old stone walls, windows stand open to the hills beyond, and the afternoon begins over coffee beneath the pergola. As you wander through the studio and gardens with the resident artist, conversation drifts towards creativity, inspiration and the courage to follow what we love.

Home
The long table

At a secluded farmhouse, simple food and local wine are laid out around a long table. Your hosts share the story of arriving when little more than crumbling stone walls stood here, and the years spent transforming them into a beautiful home, one careful decision at a time.

Presense
Into the woods

The ancient oak woods that blanket the hills beyond Val d'Orcia hide one of Tuscany's most prized treasures. A local truffle hunter and their dogs lead the way, weaving through the woodland, following imperceptible scents. Later, over a simple lunch prepared with the morning's find, conversation covers the changing seasons, patience and a life lived close to the land.

Reflect
The road ahead

Walking one last stretch through the Val d'Orcia, the rolling hills, cypress-lined lanes and isolated stone farmhouses somehow look a little different. Alongside memories of Tuscany's beauty, perhaps you carry home something else: the curiosity to imagine what the next chapter of your own life might become.

On the journey
Signature moments, curated around you

Every experience is thoughtfully shaped around your interests, pace and the season, while staying true to the spirit of the journey.

  • Curated walking routes through Val d'Orcia
  • Walk and taste with a local winemaker
  • Private visit to an artist’s Tuscan studio
  • Long lunch at a restored farmhouse
  • Truffle hunting with local expert and dogs
  • Shared meals and unhurried conversations
  • Curated Tuscan stays and restaurants
  • Private experiences and trusted local hosts
  • Seamless transfers throughout
Where you'll stay
Tuscan retreats

For this journey, we typically recommend beautifully restored farmhouses, vineyard estates and characterful countryside retreats in the heart of the Val d'Orcia. With warm hospitality and deep connection to the surrounding landscape, they create the perfect base between walks, conversations and long lunches beneath the Tuscan sun.

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