Tuscany and L'Eroica

by Ciclismo Classico
Region
Tuscany
Duration
7 days
Guided Status
Guided
Difficulty
Intermediate
D-Score™
D2 - Intermediate

Overview

If diving into a Tuscan landscape by bicycle is your idea of heaven on earth and riding back in time on the world's most legendary vintage ride seems like a pure pedaling nirvana, this one's for you! Experience the beauty of Tuscany on a seven-day journey filled with picturesque roads, unforgettable meals, and exceptional wines. Our adventure begins in the peaceful countryside of Serre di Rapolano and winds through the Val d’Orcia toward the Chianti region, where twisting streets and warm, stone-brick villages create an atmosphere straight out of a storybook. Each day, we pedal past olive groves and vineyards, soaking in the romance and nostalgia of classic cycling. The journey culminates in Gaiole at the legendary L’Eroica vintage cycling festival, where riders from around the world gather to take on Tuscany’s iconic white gravel roads in a celebration of sport, camaraderie, and pure joy.

Daily Ride Schedule

Day 1: Serre di Rapolano Warm-up Ride

24 km 274 m

D1

Serre di Rapolano Warm-up Ride

Day 2: Val D'Orcia Loop to Pienza

64 km 1006 m

D2

Val D'Orcia Loop to Pienza

Day 3: Montalcino

56 km 792 m

D1

Montalcino

Day 4: Radda in Chianti

56 km 1067 m

D1

Radda in Chianti

Day 5: Radda in Chianti Gravel Loop

40 km 732 m

D1

Radda in Chianti Gravel Loop

Day 6: L'Eroica

48 km 732 m

D1

L'Eroica

Day 7: Arrivederci!

Arrivederci!

Accommodation & Services

Accommodation

Hotel

What's Included

Airport transfers
Catering services
Accommodation arrangements
Bike rental
Mechanical support
Support vehicle following all rides

About the Tuscany

Read full regional guide