Monticchiello Travel Guide

Tourist Guide
Monticchiello showing signage
Breathtaking natural landscapes, a storybook medieval quarter and community theater productions await in this peaceful hilltop town above the Val d’Orcia.

Monticchiello is one of the many towns with gorgeous scenery that you can visit while touring Tuscany’s Siena province. The town’s origins trace back to Roman times and it flourished as a medieval stronghold from the mid-1200s. Today, Monticchiello is recognised for its close-knit community spirit, summer theatre productions and agritourism.

The town’s historic quarter is a compact, walled area that appears as though it has been plucked from a movie set. Spacious streets lead to brick-paved squares framed by stone houses with flower-filled balconies and shuttered windows. Punctuating the skyline are seven towers that have survived since the towns heyday. Two of them flank the main gateway, Porta Sant’Agata.

One of the most important landmarks is Chiesa dei Santi Leonardo di Limoges e Cristoforo. This 13th-century Gothic church dominates the sleepy Piazza Commenda. Venture inside to admire frescoes created by artists of the Siense School. Pietro Lorenzetti and Pietruccio di Betto are among the painters whose works decorate the walls.

A great time to visit is in July and August when the Teatro Povero puts on its annual show. Local residents write, direct, choreograph and perform every aspect of the shows, which bring to life social and political issues relevant to the town. Performances are open-air and run from Tuesday to Sunday.

Monticchiello is a burgeoning agritourim destination. Farms in the immediate surroundings present opportunities to get up-close with Tuscany’s stunning countryside. Relax at the farms’ swimming pools, dine on locally sourced produce and explore the region on rented bike. Similarly, the green landscapes and terraced fields of nearby Riserva Naturale Lucciolabella and Riserva Naturale Pietraporciana are a photography- and nature-lover’s paradise.

Monticchiello is just a 20-minute drive from Pienza and Montepulciano and easy to visit on a daytrip from both towns. Parking is available at the entrance to the old town. Active visitors might want to get here on foot via the hilly country lanes of the Val d’Orcia.

Hotel Relais II Chiostro di Pienza
Hotel Relais II Chiostro di Pienza
4 out of 5
Corso Rossellino 26, Pienza, SI
The price is £63 per night from 5 May to 6 May
£63
per night
5 May - 6 May
Stay at this 4-star hotel in Pienza. Enjoy free breakfast, free WiFi and an outdoor pool. Popular attractions Palazzo Piccolomini and Historic Centre of Pienza ...
8.6/10 Excellent! (483 reviews)
"Was excellent great location great staff"

Reviewed on 27 Apr 2024

Hotel Relais II Chiostro di Pienza
Affitacamere Maria Gabriella
Affitacamere Maria Gabriella
Via Marino Cappelli, 6, Pienza, Siena
Stay at this business-friendly townhouse in Pienza. Enjoy free breakfast, free WiFi and free parking. Popular attractions Art Studio di Adelina Quadri and Triacca ...
9.6/10 Exceptional! (19 reviews)
"An amazing property in the country. Fantastic views, especially at sun set. Convenient to 3 nice restaurants within 5 minutes walking. Great breakfast with many options. Room was spacious with everything you needed. A great place to stay in the area for several days."

Reviewed on 25 Oct 2023

Affitacamere Maria Gabriella
Rosewood Castiglion del Bosco
Rosewood Castiglion del Bosco
5 out of 5
Localita Castiglion del Bosco, Montalcino, SI
The price is £1,329 per night from 15 May to 16 May
£1,329
per night
15 May - 16 May
Stay at this 5-star luxury hotel in Montalcino. Enjoy free WiFi, free parking and 2 outdoor pools. Popular attractions Castiglion del Bosco Winery and Corte ...
9.8/10 Exceptional! (47 reviews)
"Best service we have ever received! They are so friendly and accommodating! Will definitely visit again"

Reviewed on 19 Nov 2023

Rosewood Castiglion del Bosco
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Hotel San Gregorio
Hotel San Gregorio
3 out of 5
Via Della Madonnina 4, Pienza, Siena
Stay at this 3-star business-friendly residence in Pienza. Enjoy free WiFi, an outdoor pool and 2 hot tubs. Popular attractions RI Crea RE and Enoteca Di Ghino ...
9.2/10 Wonderful! (93 reviews)
"Very nice staff, great service, super clean. Will stay again."

Reviewed on 11 Apr 2024

Hotel San Gregorio
Casanova - Panoramic Rooms and Suites
Casanova - Panoramic Rooms and Suites
3 out of 5
Strada Provinciale 146 di Chianciano, Località Casanova 6/c, San Quirico d'Orcia
Stay at this 3-star spa residence in San Quirico d'Orcia. Enjoy free breakfast, free WiFi and an outdoor pool. Popular attractions Palazzo Chigi and Horti Leonini ...
9.2/10 Wonderful! (17 reviews)
"Beautiful location convenient to many Tuscany sites."

Reviewed on 22 Oct 2023

Casanova - Panoramic Rooms and Suites
Casale Immerso nel Verde Della Campagna Toscana con Piscina Privata e Vista
Casale Immerso nel Verde Della Campagna Toscana con Piscina Privata e Vista
Murlo, Provincia di Siena
Stay at this holiday home in Murlo. Enjoy free WiFi, private pools and on-site parking. Popular attractions Basso Merse Nature Reserve and Castello di Montepescini ...
9.4/10 Exceptional! (34 reviews)
2 weeks in the Tuscan hills
"The house is a beautiful old Italian house with high ceilings with wooden beams and tiled floors. Everything in the house worked pedfectly- wifi, hot water, screens on the windows, kitchen and bath. The house is set in the midst of the Tuscan hills with hikes starting right from the front door. The ..."

Reviewed on 12 Oct 2023

Casale Immerso nel Verde Della Campagna Toscana con Piscina Privata e Vista
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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