A quaint, tiny hamlet on the hills surrounding Pienza


Sitting just behind Pienza, this small hamlet that counts just 202 inhabitants has a very significant history. During the Middle Ages it was a very influential town thanks to its convenient position on a hilltop, which unfortunately went through a phase of decline whilst under the ruling of the Medici family from Florence.

The road that leads up to the hamlet is one of Tuscany’s most famous routes, flanked by beautiful cypresses on either side as it slopes up the hill. Monticchiello is known for having various romitorios around it. Caves carved into the rock by hermit monks which feature beautiful carvings of Medieval origin. Another unique feature of Monticchiello is its teatro povero, an open air theatre created during a time of profound crisis in the town, a theatre which concentrates more on the acting rather than costumes and prop design. Each community member has a role in each play, as a way of involving everyone and reinstating a sense of community. A play has been put on every summer for the past 50 years.

Bike & Walk

Bagno Vignoni to Monticchiello to La Foce

3 hour e-bike itinerary

Begin your bicycle journey in Bagno Vignoni, making your way down the SP53, turn left at the intersection with Pienza, then turn right, following the signs for Monticchiello. Bike up the famous cypress lined road, make your way to Monticchiello, turning right just before town on the SP88. Turn right again after roughly 3km towards La Foce. Keep the villa on your left as you cycle down the hill, turning right for the Riserva Naturale Lucciola Bella and the steep, infamous road. Ride back down the hill on the opposite side and join the SP53 which brings you straight back to Bagno Vignoni. Don’t forget to bring plenty of water!

Image by The Fork


Osteria La Porta

food & view

Sitting right above the Medieval walls is a quaint little restaurant with sweeping views of Val d’Orcia and delicious local food.

Image by Ristorante Daria

Ristorante Daria

innovative Tuscan

Tradition meets innovation with a great wine list and host, buried deep in the Medieval hamlet.

Image by Restaurant Guru

La Guardiola

wine & cocktails

Sip whatever beverage you please sitting under fairy lights on a terrace overlooking Val d’Orcia, accompanied by the perfect summer breeze.

Image by L'Olmo



chic farmhouse

A boutique hotel in a restructured traditional Podere a short 5 minute drive from Monticchiello.

Image by B&B Daria

B&B Daria

central bed & breakfast

Axperience life in a Medieval hamlet in this cosy three-bedroom B&B with a garden and hot tub.

Image by La Casa di Adelina

La Casa di Adelina

entire house

A selection of three rustic farmhouses to choose from in Monticchiello’s centre.