Monticchiello

Travel Guide

Monticchiello showing a small town or village and heritage architecture as well as an individual femail
Monticchiello which includes signage
Monticchiello featuring heritage architecture and flowers
Monticchiello showing a small town or village as well as a couple
Monticchiello showing flowers and heritage architecture

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 recognized for its close-knit community spirit, summer theater 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 PienzaOpens in a new window and MontepulcianoOpens in a new window 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
Stay at this 4-star hotel in Pienza. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions ...
8.6/10 Excellent! (595 reviews)
Stunning setting - authentic italian
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Reviewed on Aug 25, 2025

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Nuovo Etruria Resort

Nuovo Etruria Resort

Via di S. Martino snc, Montepulciano, SI
The price is P6,885 per night from Nov 2 to Nov 3
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Stay at this hotel in Montepulciano. Enjoy an outdoor pool, breakfast (surcharge), and daily housekeeping. Popular attractions Colonna del Marzocco and Palazzo ...
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Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

5 out of 5
Via Poggio alla Sala 10, Montepulciano, SI
The price is P22,326 per night from Nov 1 to Nov 2
P22,326
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Nov 1 - Nov 2
includes taxes & fees
Stay at this 5-star luxury hotel in Montepulciano. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff in our reviews. ...
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Reviewed on Sep 27, 2025

Precise Tale Poggio Alla Sala
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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Casanova - Panoramic Rooms and Suites

3 out of 5
Strada Provinciale 146 di Chianciano, Località Casanova 6/c, San Quirico d'Orcia, SI
Stay at this 3-star residence in San Quirico d'Orcia. Enjoy free breakfast, free WiFi, and an outdoor pool. Popular attractions Horti Leonini and Chapel of our ...
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Reviewed on Sep 24, 2025

Casanova - Panoramic Rooms and Suites
Hotel San Gregorio

Hotel San Gregorio

3 out of 5
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Stay at this 3-star business-friendly residence in Pienza. Enjoy free WiFi, an outdoor pool, and room service. Popular attractions RI Crea RE and Enoteca Di ...
9.2/10 Wonderful! (129 reviews)
Pienza getaway
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Reviewed on Sep 1, 2025

Hotel San Gregorio
Abbadia Sicille Relais

Abbadia Sicille Relais

4 out of 5
SP 14 Loc. Abbadia Sicille, Trequanda, SI
Stay at this 4-star business-friendly residence in Trequanda. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Monastery of Sant'Anna ...
8.8/10 Excellent! (155 reviews)
An amazing find. Would love to return
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Reviewed on Nov 30, 2024

Abbadia Sicille Relais
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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