Typical cypress trees in Tuscany

Trails of Tuscany

With its golden landscape dotted with ancient wine-making villages, olive groves, and rows of Cypress trees, Tuscany is best explored on foot. This is an authentic experience exploring the quiet trails, iconic scenery, and highlights of Tuscany. Travel at your own pace through the rolling countryside and visit medieval walled towns and hilltop villages along the way. Visit Renaissance cities and enjoy free time to immerse yourself in the local culture and traditions. Florence feels like a living museum filled with world-class art and architecture, and walking through Siena's city gates feels like stepping back in time. Paired with incredible food, this is a slow adventure that we know you're going to love.  

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updated on: November 07, 2022
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Viewing format
recommended route Difficulty easy
Distance 15.4 km
Duration 5:05 h
Ascent 522 m
Descent 464 m

Walk from Pienza back to Montepulciano via the small, fortified hamlet of Monticchiello.

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recommended route Difficulty easy
Distance 9.1 km
Duration 3:00 h
Ascent 37 m
Descent 269 m

Half day walk through the iconic Tuscan countryside of yellow fields and hilltop villages to Acquaviva.  Alternative: there is the option to do ...

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recommended route Difficulty easy
Distance 7 km
Duration 2:10 h
Ascent 3 m
Descent 49 m

An optional extension that creates a longer full day walk from Montepulciano to Valiano before transferring from there to Cortona.  

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Hiking route · Italy
Cortona Loop Walk
recommended route Difficulty moderate
Distance 12.8 km
Duration 4:30 h
Ascent 397 m
Descent 406 m

A short circular walk from your hotel in Cortona with views to southern Tuscany and possible side visits exploring a medieval fortress and ...

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Hiking route · Firenze
Florence Loop Walk
recommended route Difficulty easy
Distance 6.3 km
Duration 2:20 h
Ascent 113 m
Descent 113 m

Loop walk to take in Florence's main attractions at your own pace.

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