Tuscany: Hilltop Towns

Walk between Renaissance and medieval hill-top towns of southern Tuscany, discovering Montepulciano, Pienza, Bagno Vignoni, Montalcino, and finally Siena. Your journey winds through a unique linear, almost geometric landscape of hills, vineyards and olive trees. Highlights include the spa baths at Bagno Vignoni and former Benedictine monastery at Sant’ Antimo Abbey. You’ll follow rewarding trails through the lesser known wine regions south of Siena. Take your time, slow down and discover the tastes and textures of Tuscany, one of Italy’s most beautiful and historic regions.

Public list
outdooractive.com User
List created by
Chase Marston
updated on: May 16, 2019
Responsible for this content
Macs Adventure Verified partner  Explorers Choice 

Viewing format
Hiking trail · Siena

Montepulciano to Pienza

July 26, 2017
moderate
15.5 km
4:45 h
490 m
543 m
A lovely walk through undulating and iconic landscapes, passing wineries, vineyards and olive groves galore and finishing in the splendid hill top ...
1
from Sally Thompson,   Macs Adventure
Hiking trail · Siena

Pienza to Bagno Vignoni

July 26, 2017
moderate
15.4 km
6:00 h
312 m
495 m
A lovely walk beginning in Pienza and finishing in the spa village of Bagno Vignoni with consistently fantastic views.
3
from Sally Thompson,   Macs Adventure
Hiking trail · Siena

Bagno Vignoni to Sant' Antimo

July 26, 2017
moderate
14.5 km
5:00 h
489 m
475 m
Follow trails through a series of different landscapes including woods and farmland with sweeping valley views of vineyards and castles on hilltops.
2
from Sally Thompson,   Macs Adventure
Hiking trail · Siena

Montalcino to Buonconvento

July 26, 2017
moderate
16.9 km
5:00 h
274 m
531 m
A linear route from the hill top town of Montalcino to the Pieve a Salti Agriturismo with constant views of the Crete Senesi.
3
from Sally Thompson,   Macs Adventure
July 26, 2017
moderate
10.7 km
3:15 h
293 m
356 m
Walk from the impressive Monte Oliveto Maggiore Monastery on a variety of different terrain with fantastic views everywhere you turn.
1
from Sally Thompson,   Macs Adventure
Hiking trail · Siena

Grancia di Cuna to Siena

July 26, 2017
moderate
16.9 km
4:30 h
237 m
116 m
A walk that begins at the Grancia di Cuna, a 12th century hospice and hospital for pilgrims on the Via Francigena and ends in Siena, a UNESCO ...
1
from Sally Thompson,   Macs Adventure