Tuscany
An eight-day, 140 km journey across the rolling hills of Tuscany
In May 2026, my wife and I hiked from San Gimignano to Montepulciano, passing through Siena, Montalcino, and Pienza. Around three-quarters of the route followed the Via Francigena, a 3,200 km ancient pilgrimage trail stretching from Canterbury to Rome. Along the way, we crossed three distinct valleys: Val d’Elsa, Val d’Arbia, and the UNESCO-listed Val d’Orcia.
Tuscany is a region of medieval towns, valleys and ridges, rolling clay hills, and white gravel tracks lined with cypress trees. Its landscapes shift from vineyards and olive groves to forests and wide-open fields, making it exceptionally rewarding for long days on foot.
Below are links to the daily hiking logs; you’ll also find the posts with images and excerpts at the bottom of the page. The full story is coming soon.
- Day 1: San Gimignano to Colle di Val d’Elsa
- Day 2: Colle di Val d’Elsa to Monteriggioni
- Day 3: Monteriggioni to Siena
- Day 4: Siena to Buonconvento
- Day 5: Buonconvento to Montalcino
- Day 6: Montalcino to San Quirico d’Orcia
- Day 7: San Quirico d’Orcia to Pienza
- Day 8: Pienza to Montepulciano
Full story coming soon
Daily Hiking Logs
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Tuscany Day 1: San Gimignano – Colle di Val d’Elsa
The start of our journey: from the “Manhattan of the Middle Ages” to the “Bohemia of Italy”
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Tuscany Day 2: Colle di Val d’Elsa – Monteriggioni
From riverside trails and river crossings to ancient thermal pools and a medieval hilltop fortress
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Tuscany Day 3: Monteriggioni – Siena
A rain-soaked walk from Monteriggioni’s medieval walls through forest tracks to Siena’s UNESCO-listed centre
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Tuscany Day 4: Siena – Buonconvento
Walking into the Val d’Arbia towards the Crete Senesi – Tuscany’s iconic landscape of rolling hills, multi-coloured fields, and cypress trees
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Tuscany Day 5: Buonconvento – Montalcino
Cypress avenues, wine estates, and a steep ascent to a medieval hilltop town known for Brunello wine
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Tuscany Day 6: Montalcino – San Quirico d’Orcia
Leaving Montalcino’s ridge and the Val d’Arbia in sunshine before entering the UNESCO-listed Val d’Orcia in the rain
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Tuscany Day 7: San Quirico d’Orcia – Pienza
A walk through the Val d’Orcia’s rolling hills, past ancient thermal pools, and up to a UNESCO-listed Renaissance hilltop town
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Tuscany Day 8: Pienza – Montepulciano
A final day of climbs, descents, and sweeping Tuscan views, ending in a medieval hill town known for its wine and Renaissance architecture