Tuscan Hills

Tour of Tuscany: Florence to Montepulciano

Take on our Tour of Tuscany cycling from Florence, through the world-class winelands of Chianti and Montepulciano.

Ride the rolling Chiantigiana to Radda in Chianti and Tuscany’s largest collection of wine, ‘Casa del Chianti’. Follow stages of Giro d’Italia to the towers of San Gimignano and the buzz of Siena’s Piazza del Campo (perfect for a post-ride vino rosso!). Ride the exquisite Val d’Orica and round off your tour with a glass of the reputed Vino di Nobile in medieval Montepulciano.
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Jo Payne
updated on: December 08, 2017
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Viewing format
recommended route Difficulty moderate
Distance 46.6 km
Duration 2:43 h
Ascent 850 m
Descent 450 m

Ride into the heart of Chianti via the local and pro’s favourite route, the 'Via Chiantgiana'. Leaving Florence visit the museum of Tour de France ...

from Jo Payne,   Macs Adventure Ltd
Road biking · Radda in Chianti
Road Cycling: Radda in Chianti Loop Ride
Difficulty difficult
Distance 50.1 km
Duration 3:43 h
Ascent 1,150 m
Descent 1,152 m

Take in a loop ride through the Chianti wine lands. Tap out a steady rhythm on the climb to Giaole in Chianti, home to 12th century Brolio Castle, ...

from Jo Payne,   Macs Adventure Ltd
Difficulty moderate
Distance 31.1 km
Duration 2:07 h
Ascent 630 m
Descent 631 m

Please refer to your route notes for a shorter distance avialable on this day. Take in a loop ride through the Chianti wine lands.

from Jo Payne,   Macs Adventure Ltd
Difficulty difficult
Distance 74.4 km
Duration 3:59 h
Ascent 1,000 m
Descent 1,100 m

Leaving Radda, cycle sections of the Giro d’Italia stages as you head west to the hilltop town of San Gimignano famed for it’s 14 towers (and the ...

from Jo Payne,   Macs Adventure Ltd
Difficulty moderate
Distance 57.3 km
Duration 3:01 h
Ascent 800 m
Descent 800 m

Please refer to your notes notes for a shorter ride available on this day. Leaving Radda, cycle sections of the Giro d’Italia stages as you ...

from Jo Payne,   Macs Adventure Ltd
Difficulty difficult
Distance 57.2 km
Duration 3:35 h
Ascent 1,000 m
Descent 1,000 m

Cycle the Montagnola Hills west of Siena. Take a spin to the fortified town of Sovicille. Roll through the hills of Poggio al Pero and through the ...

from Jo Payne,   Macs Adventure Ltd
Difficulty moderate
Distance 61.1 km
Duration 3:26 h
Ascent 850 m
Descent 700 m

Ride to the world class wine region of Montepulciano. An easier spin on the legs today heads through lands rich in wine, olive and sunflower ...

from Jo Payne,   Macs Adventure Ltd
Difficulty difficult
Distance 90.3 km
Duration 5:21 h
Ascent 1,434 m
Descent 1,437 m

Before being lured by the countless wine tasting experiences, there are a choice of two rides today. A long but punchy route heads through the ...

from Jo Payne,   Macs Adventure Ltd