Before leaving Montalcino, springtime host of L’Eroica, take a moment to enjoy the breathtaking views from the Giardini dell’Impero and visit the medieval fortress. The descent will be a delightful ride through vineyards, surrounded by Tuscany’s natural beauty.

A short stretch marks the split between L’Eroica and Eroica Montalcino, leading into the stunning landscapes of Val d’Orcia. In the medieval village of San Quirico d’Orcia, a key stop on the Via Francigena, you can admire the Horti Leonini and the iconic cypress trees.

After San Quirico d’Orcia, a stop at the Chapel of the Madonna di Vitaleta, framed by cypress trees, is a must. Continuing towards Bagno Vignoni, you pass through Vignoni Alto with views of Val d’Orcia before arriving at the famous medieval thermal baths.

A climb leads to the entrance of Pienza, the Renaissance city of Pope Pius II, renowned for its Pecorino cheese and breathtaking views of Val d’Orcia. Strolling through its streets, you’ll feel the harmony of an "ideal" city overlooking the rolling Tuscan hills.

On the white road of Le Regge, the ridges offer stunning views. Nearby, the village of Petroio captivates with its terracotta craftsmanship before the route heads to Osteria delle Noci, where spectacular vistas of Val d'Orcia and Val di Chiana await.

Before reaching Montisi, a medieval village of Etruscan origin, the stunning olive terraces, yielding the famous Tuscan olive oil, will capture your heart.

In the heart of the Crete Senesi, between Trequanda and San Giovanni d’Asso, the biancane and calanchi create breathtaking views. In autumn, the region celebrates the famous white truffle with the White Diamond Market.

Buonconvento, one of Italy's most beautiful villages, retains the timeless atmosphere of the Via Francigena. The vast truffle fields of the Crete Senesi enrich the landscape, while the Eroica Montalcino route intersects with the classic L’Eroica.

Leaving Buonconvento, you tackle the famous climb of Castiglione del Bosco, passing through the authentic Tuscan countryside. The route offers views of vineyards and cypress trees, with the imposing Poggio alle Mura Castle at the heart of the Brunello region.

A gravel road climb leads to Sant’Angelo in Colle, a circular medieval village with a central square facing the Church of San Michele Arcangelo. Here, among olive groves and cypress trees, you’ll find a stunning view of the Tuscan hills and Brunello vineyards.

After leaving Sant’Angelo in Colle, a captivating gravel road leads to the Abbey of Sant’Antimo, surrounded by tall cypress trees and centuries-old olive groves. The nearby village of Castelnuovo dell’Abate overlooks this landscape rich in Brunello di Montalcino wineries.

The return to Montalcino gently winds through Brunello wineries. Just before reaching the town, cyclists are welcomed by the famous cypress-lined avenue of the Biondi Santi Winery, a symbol of this prestigious red wine.

Camigliano, a hidden medieval village, preserves historic monuments from the 13th century, like the Church of Santi Biagio and Donato.

Between the hills of Val d’Orcia and the forests of Monte Amiata, Castiglion d’Orcia offers historic villages and breathtaking landscapes. The recently restored Aldobrandeschi Fortress towers over the area, adding to its timeless charm.

The charming medieval village of Chiusure, nestled in the Crete Senesi, is a gem of history and tradition. Just a few kilometers away stands the majestic Abbey of Monte Oliveto Maggiore, a place of great charm and spirituality.

Cinigiano, a village at the foothills of Monte Amiata, offers a route through the breathtaking landscapes of the Maremma. Among hills, forests, and vineyards, you’ll discover the villages of Porrona and the fortresses of Castiglioncello Bandini and Vicarello.

This route variant passes through Seggiano, a hidden gem rich in surprises. Known for the Olivastra Seggianese, which produces a top-quality DOP olive oil, Seggiano is a must-visit for those seeking authentic Tuscan experiences.