Val D’Orcia Guided 7 Days Road

difficulty level

Hard

Exp. level

Advanced

route type

Road

rec. perdiod

Located south of Siena, in southern Tuscany, the Val d’Orcia is renowned for its breathtaking landscapes featuring rolling hills, vineyards, cypress trees, and medieval villages. Declared a UNESCO World Heritage Site in 2004, the area is famous for its natural beauty and the production of prestigious wines such as Brunello di Montalcino and Nobile di Montepulciano. Rich in history, the Val d’Orcia boasts fascinating towns like Pienza, Montalcino, Montepulciano, and San Quirico d’Orcia, which highlight the region’s cultural and artistic significance over the centuries. Ideal for nature lovers, food enthusiasts, and history buffs, the Val d’Orcia offers a unique experience of immersion in Tuscan tradition.

Day 1: Bike assembly and saddle position 30 km, 600 m

In the morning, guests will arrive at Florence Airport, where the Slice Adventures staff will transfer them to the accommodation in Montepulciano, where they will stay for the entire vacation. After settling into their rooms, lunch will be served. Later, a professional mechanic will assist guests in unpacking and assembling their bikes or adjusting the position for those who have rented bikes. Once everyone is ready, a test ride will be conducted to check the bikes and saddle positions. Dinner: At the accommodation.

Day 2: 85 km, 1569 m

Starting from Montepulciano, the route begins with a gentle descent into the surrounding countryside. After a few kilometers, you’ll reach Torrita di Siena, a picturesque medieval village with walls and towers. Cycling along quiet roads, you’ll pass rolling hills, olive groves, and vineyards typical of the Crete Senesi landscape. The route continues toward Chianciano Terme, known for its thermal baths and curative waters. Positioned on a hilltop, Chianciano offers spectacular views of the surrounding valleys. Next, the journey leads to Monticchiello, an enchanting medieval village with ancient walls and an open-air theater offering extraordinary views of the valley below. The gentle climbs and panoramic descents make the ride to Monticchiello a true highlight. The day concludes with a return ride to Montepulciano. Dinner: At the accommodation.

Day 3: 74 km, 1569 m

The day begins with a visit to Monticchiello, followed by a ride to San Quirico d’Orcia, a charming Tuscan village known for its rich historical and artistic heritage. Here, you can visit the Collegiata di San Quirico e Giulitta and the beautiful Horti Leonini Italian gardens. From San Quirico, the route continues to Torrenieri, a peaceful village overlooking the Val d’Orcia. Next is Montisi, a medieval gem with stone houses and narrow streets that feel frozen in time. The ride ends with a visit to Trequanda, an enchanting village atop a hill offering spectacular views of the surrounding valleys. Dinner: At the accommodation.

Day 4: Rest Day

Cooking class and/or guided tour of the San Casciano dei Bagni archaeological site, followed by dinner in San Casciano.

Day 5: 93 km, 1830 m

Begin the day with a visit to Pienza, known for its Renaissance architecture and UNESCO designation as the “ideal city” envisioned by Pope Pius II. Explore its picturesque streets, main square, Cathedral, and Palazzo Piccolomini, and perhaps sample its famous Pecorino di Pienza cheese. From Pienza, the route continues to San Quirico d’Orcia, with panoramic views of cypress trees and rolling hills. Next is Montalcino, renowned for its Brunello di Montalcino wine. Visit the Fortress of Montalcino, which offers breathtaking views, and enjoy a wine tasting at a local winery. The tour proceeds to Castelmuzio, a small, authentic medieval village with spectacular views, before returning to Montepulciano. Dinner: At the accommodation.

Day 6: 101 km, 2454 m

This is the most challenging route of the week, culminating in a climb to the summit of Monte Amiata. Begin with a visit to Chianciano Terme, a renowned spa town with curative waters, before heading to Sarteano, a medieval village with a castle, the Church of San Francesco, and Etruscan heritage at the Archaeological Museum. The route climbs toward Abbadia San Salvatore, situated on the slopes of Monte Amiata, an ancient volcano. Visit the Abbey of San Salvatore, dating back to the 10th century. Descending from Monte Amiata, the route passes through Castel del Piano, a tranquil village surrounded by olive groves and vineyards, and then to Seggiano, offering breathtaking views of the Tuscan countryside. The ride concludes with a van transfer back from Castelnuovo dell’Abate. Dinner: At the accommodation.

Day 7: Bye Bye

Breakfast at the accommodation and transfer to Florence Airport.

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