Classic Tuscany

Treat yourself to a week under the Tuscan sun; slow down to take in the classic sights of Volterra, San Gimignano, Colle Val D’Elsa Monteriggioni and Siena on foot—the best way to relax and immerse yourself in Tuscany. Follow trails between hilltop towns, set against an undulating patchwork of vineyards and villas. Farmhouse lunches are filled with local organic gourmet goodies— matured pecorino, soft ricotta, homemade pasta, saffron treats, sweet vin santo and castagnaccio chestnut cake. This week-long trip includes 2 nights each in Volterra, San Gimignano and Siena, combining rewarding walks with time to lose yourself in the medieval, Renaissance and Gothic architecture.
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updated on: May 06, 2022
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Hiking route · Italy
Volterra Loop Walk
Difficulty moderate
Distance 17.3 km
Duration 4:55 h
Ascent 429 m
Descent 143 m

Enjoy a glorious walk through typical Tuscan scenery, looping back round to Volterra.

from Anna Wren,   Macs Adventure
recommended route Difficulty moderate
Distance 21.2 km
Duration 6:21 h
Ascent 488 m
Descent 547 m

This rural walk takes you through nature reserves and ancient villages before climbing up to the UNESCO World Heritage Site of San Gimignano.

from Sarah Stone,   Macs Adventure
Hiking route · Italy
San Gimignano Loop Walk
Difficulty easy
Distance 15.7 km
Duration 4:29 h
Ascent 451 m
Descent 451 m

Venture out of San Gimignano into the patchwork landscape of vineyards and woodland for a rewarding loop walk.

from Anna Wren,   Macs Adventure
Difficulty moderate
Distance 25.1 km
Duration 7:16 h
Ascent 441 m
Descent 630 m

Ahead lies a long but enjoyable day of walking along the famous Via Francigena, the ancient pilgrimage route which stretches from Canterbury to Rome.

from Sarah Stone,   Macs Adventure
Hiking route · Italy
Monteriggioni to Siena
Difficulty moderate
Distance 20 km
Duration 5:37 h
Ascent 402 m
Descent 304 m

Leaving Monteriggioni on foot, follow in the pilgrims footsteps along the Via Francigena to Siena. 

from Sarah Stone,   Macs Adventure