DRIVING LOOPS – 1. Ring Pienza – Montepulciano – La Foce

Starts and ends: Agriturismo Il Rigo
Route length: circa 70 km

This is probably the most iconic itinerary to make if you have just one day to spend in Valdorcia, discovering the well know beauties of is the “touchstone of Renaissance urbanism”, the village of Pienza. The route will guide you than to the beautiful rolling hills of the Tuscan countryside, heading the village of Moticchiello, passing by cheese farms and wineries of Orcia DOC, and than Montepulciano and its historic cellars, the renowned cypress winding road of La Foce, to come back home at Il Rigo, just in time for dinner!

1. Cappella di Vitaleta

Before you reach road SP146, stop by the Cappella di Vitaleta.

2. Pienza

Continue on toward Pienza, where you can spend a nice hour, walking on the main street and on the old city walls, looking at the Valley. Head back to the 146 and drive to Montepulciano.

3. Monticchiello

An optional extension passes by the village of Monticchiello. Along this road, consider stopping for a wine tasting by Capitoni (reservation is required) or for a cheese tasting and farm visit at Il Casale. You can just stay on the SP146, and about 10km further along Palazzo Massaini you will reach Montepulciano.

4. Montepulciano

Stop by the church of San Biagio before climbing the mountain of Montepulciano. The town is well known for its historic wine cellars and the beautiful palaces of the centre. Cantina del Redi is called “wine cathedral” and the Contucci cellars are almost 100m deep!

5. La Foce

On Wednesday and in the weekend, you can enjoy a visit at La Foce’s Gardens  (if you’re fond of gardens read the post about our favourites in Val d’Orcia). To reach it, follow the SP146 from Montepulciano and after a couple km, turn right onto the SP88 (follow the brown signs pointing to “Castelluccio”). When you reach Villa, stop to admire the curvy cypress road, an icon of Tuscany. For a snack before the visit, we suggest Dopolavoro della Foce, just in front of the Villa’s gate. This visit lasts about an hour.

6. Quercia delle Checche

You should have enough time to watch the sunset under the Quercia delle Checche, a 300-year-old oak tree! Still have some time left? Stop by local pasta producer Mulino della Valdorcia to buy some organic flour. Head to the Cassia (SR2) and turn right to intersect the crossing for Il Rigo.


Where to eat:
Sette di Vino € – +39 0578 749092
La Bandita €€€ – + 39 0578 749005
Buon Gusto (ice cream)
Daria (Monticchiello) – +39 0578 755163
Idyllium (cocktail bar and snacks) – +39 0578 748176

Where to shop:
Il cacio di Ernello (Pecorino di Pienza)
Biagiotti (ferro battuto)
Aracne (weaving lab)

Where to eat:
Osteria Acquacheta €€ – +39 0578 717086
Logge del Vignola €€€ – +39 0578 717290
Caffè Poliziano €€ – +39 0578 758615
Azienda Cugusi (pin nic) – +39 0578 757558
Dopolavoro della Foce €€ – +39 0578754025

Where to shop:
Rameria Mazzetti


DRIVING LOOPS – 2. Brunello’s ring

DRIVING LOOPS – 3. Through the Crete Senesi

DRIVING LOOPS – 4. Into the wild – Amiata and Radicofani


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