Day 1 – Arrive in Siena

Start your morning in Piazza del Campo, the heart of the city, and climb the Torre del Mangia for sweeping views. Visit the stunning Siena Cathedral (Duomo) with its intricate marble floors, then stroll through the medieval streets to soak in the atmosphere. Pause for lunch with local specialties like pici pasta, and spend the afternoon exploring hidden alleys, artisan shops, and the city’s historic contrade. End your day with a sunset walk along the city walls for a perfect Tuscan panorama.

Day 2 – Siena to Buonconvento 37 Km / 23 Mi

The journey from Siena to Buonconvento will be a ride to the taste of the rural Tuscany, leaving Siena by the beautiful, panoramic road of Ville di Corsano, and all the way to Murlo, you will find open landscapes of grain with changing colours, fields of sunflowers, farmhouses with production of local cheese and olive oil, passing through the medieval Radi and Murlo which offers wooded hills and a glimpse of Etruscan heritage. Buonconvento is a charming medieval village in the Crete Senesi, south of Siena, enclosed by 14th‑century walls and celebrated as one of Italy’s most beautiful towns.

Day 3 – Buonconvento to San Quirico d’Orcia 36 Km / 22 Mi

After leaving Buonconvento you have to climb until you arrive to the impressive Montalcino and its famous vineyards. It will be a ride of nearly 22km almost unpaved with more than 600 m of elevation gain. The ride intensifies as you ascend to Montalcino, surrounded by Brunello vineyards. The panoramic views reward the effort, with the fortress town perched high above the Val d’Orcia. Continue through rolling hills to San Quirico, a charming medieval village with gardens and stone streets that embody the UNESCO‑listed landscape.

Day 4 – San Quirico d’Orcia to Montepulciano 31 Km / 19 Mi

The special ride of today will last in your memories for ever and you will enjoy every second of it. From San Quirico all the way through Montepulciano, will be a delightful immersion in the Val D’Orcia, the impressive landscapes of this area inspired many artists with its medieval castles, rolling hills, avenues of cypresses leading to amazing villas and farmhouses, Abbeys, vineyards and olive groves.

The extreme beauty of Val D’Orcia is now protected as natural and cultural park and recognized as World Heritage Site by UNESCO. The beautiful gems of San Quirico, Bagno Vignoni, Pienza and Monticchiello will be your main stops. It will be a ride of nearly 31 km that will take you about 4 hrs and will consist of quiet roads, and open mountain riding across the most scenic landscape in Tuscany.

Day 5 – Departure from Montepulciano

Montepulciano is renowned for its wine, the town’s steep streets and grand piazzas mark a triumphant finish to the journey. Take your time to visit the ancient underground cellars and tast the Vino Nobile. From there, you can easily explore Lake Trasimeno, Cortona, and Arezzo, or travel on to Florence and Rome via highway or train.