Arrive at Borgo San Felice from Florence and immerse yourself in this charming historic hamlet and winery. Discover the piazza, chapel, and old lanes. After a bike fitting you have time for a test ride to nearby Castelli, visit Castelnuovo Berardenga with its medieval charm and Villa Chigi Saracini. Ride through the vineyards of Chianti Classico, enjoying the picturesque landscapes.
– DISTANCE 36.1 km +637 m / -632 m
– Hotel: Relais Borgo San Felice

Welcome meeting with local BTS representative at your first hotel.

Embark on a scenic loop through Radda, Badia Coltibuono, and Gaiole. Enjoy a coffee break in the hilltop town of Radda in Chianti, where history and modern life blend seamlessly. Take a wine tour and lunch at the historic Badia a Coltibuono winery, surrounded by vineyards planted by monks over a millennium ago. Visit Gaiole, renowned for the “L’Eroica” vintage bike event, and soak in the local culture.
– Hotel: Relais Borgo San Felice

Cycle through the picturesque landscapes of Monteaperti, Le Crete, Asciano, and San Giovanni d’Asso. Pause in Asciano for a perfect coffee break amidst the stunning Crete Senesi. Reach Montalcino, famed for its Brunello wine, and explore the town’s Etruscan and Roman roots. Visit the Abbey of Sant’Antimo, a masterpiece of Romanesque architecture with a serene atmosphere. End the day at Relais Mastrojanni, enjoying the tranquility of the countryside.
– Hotel: Relais Mastrojanni

Ride to the UNESCO World Heritage Site of Val d’Orcia, with stops in Bagno Vignoni and Pienza. Enjoy a coffee break in the thermal village of Bagno Vignoni, where history and relaxation meet. Discover Pienza, a Renaissance jewel designed by Pope Pius II, and stroll through its charming streets. Visit the iconic Vitaleta Chapel before heading back, capturing the essence of Tuscany.
– Hotel: Relais Mastrojanni

This moderate challenging, rise and fall stage unrolls like a film of snapshots from the past: olive and carob trees, farmhouses and villas of the rural past aristocracy. The profile of the hilly area gradually changes its shape as we get further in a harmonious plateau area. You can enjoy the spectacular views of Tellaro valley from here.
The section of the route with its continuous series of ups and downs is quite demanding, but your effort will be rewarded by views of unequalled beauty at each turn or hilltop.
You arrive in the magnificent Baroque city of Ragusa, where you can visit the awesome Iblean Garden by foot and the Old Town, called IBLA; here you will find a lot of churches, gelaterias and street food shops. Then we will loop back to Modica for the rest of the ride. For dinner, choose from many wonderful local restaurants such as hole‐in‐the‐wall trattorias to Slow Food and Michelin‐starred restaurants. (we’ll give you some favorite suggestions)
Meals included: Breakfast

Say goodbye to Tuscany any way you see fit. Sleep in, stroll around the grounds, or opt for a final early morning short loop ride.

Pedal from Montalcino to Siena through the stunning landscapes of Castiglion del Bosco and Murlo, marveling at the panoramic views. Experience the gravel paths of L’Eroica, feeling the thrill of Tuscany’s most celebrated cycling routes, the ride end in Siena outskirt.
Arrive Siena, the medieval masterpiece, and take time to explore its rich history and vibrant culture. Visit Piazza del Campo, Torre del Mangia, and the majestic Duomo, each telling a story of its own