Siena

Treasures of Tuscany & Umbria

Explore the absolute best of Tuscany and Umbria on foot; starting with the medieval and Renaissance hill-top towns of Siena and Pienza, on to historic Perugia and ending in iconic Florence. Nestled in the green heart of Italy; walk through landscapes of rolling hills, past soldier-straight lines of cyprus trees, through vineyards and olives groves. The journey begins in the UNESCO World Heritage city of Siena, then it's on to Tuscany's Renaissance hill-top towns - Montepulciano, Montefollonico/Pienza, and Montichiello. In Cortona stay in a 15th century mansion, high up on a hill. Trails in south Tuscany afford panoramic views over the olive groves, yellow plains and vineyards of the Valdichiana Valley and Lake Trasimeno. Crossing into Umbria, for a wine tasting and optional cooking lesson. Immerse yourself in Perugia's fascinating museums, markets and arcades before finally arriving in Florence, with time to discover this incredible city.

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updated on: September 21, 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.

from Macs Adventure,   Macs Adventure
recommended route Difficulty easy
Distance 9.1 km
Duration 2:55 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 ...

from Macs Adventure,   Macs Adventure
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.  

from Macs Adventure,   Macs Adventure
Hiking route · Italy
Walk from Ossaia to Tuoro
recommended route Difficulty easy
Distance 12 km
Duration 3:55 h
Ascent 307 m
Descent 326 m

Walk from Ossaia to Tuoro with views over the Valdichiana Valley and Lake Trasimeno.

from Macs Adventure,   Macs Adventure
recommended route Difficulty easy
Distance 6.8 km
Duration 2:35 h
Ascent 228 m
Descent 124 m

Chance to visit Mongiovino Abbey and Castle before walking to the hill-top village of Panicale.

from Macs Adventure,   Macs Adventure
recommended route Difficulty easy
Distance 9.1 km
Duration 3:15 h
Ascent 324 m
Descent 219 m

Chance to visit Mongiovino Abbey and Castle and take a short detour to Lupaia Lake before walking to the hill-top village of Panicale.

from Macs Adventure,   Macs Adventure
recommended route Difficulty easy
Distance 4.3 km
Duration 1:40 h
Ascent 3 m
Descent 265 m

Short walk from to Cibottola Castle to Monte Vibiano Winery for a tour and tasting.

from Macs Adventure,   Macs Adventure
recommended route Difficulty easy
Distance 11 km
Duration 3:20 h
Ascent 62 m
Descent 35 m

Wine tasting and tour at Monte Vibiano Winery before walking along the Nestore River Park to Poggio delle Corti.

from Macs Adventure,   Macs Adventure
recommended route Difficulty easy
Distance 13.5 km
Duration 4:15 h
Ascent 218 m
Descent 330 m

Transfer to Monte Tezio to begin the walk through the Tezio area with its ancient aqueducts to the capital of Umbria, Perugia. This is the ...

from Macs Adventure,   Macs Adventure
recommended route Difficulty easy
Distance 1.7 km
Duration 1:00 h
Ascent 32 m
Descent 44 m

Transfer to Monte Tezio to begin the walk through the Tezio area with its ancient aqueducts to the capital of Umbria, Perugia. This is the ...

from Macs Adventure,   Macs Adventure
recommended route Difficulty easy
Distance 16.8 km
Duration 5:25 h
Ascent 415 m
Descent 495 m

Transfer to Monte Tezio to begin the walk through the Tezio area with its ancient aqueducts to the capital of Umbria, Perugia.  This is the ...

from Macs Adventure,   Macs Adventure
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.

from Macs Adventure,   Macs Adventure