Monticchiello

Travel Guide

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

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.

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Affitacamere Maria Gabriella

Affitacamere Maria Gabriella

Via Marino Cappelli, 6 Pienza SI
$135 nightly
The price is $153 total per night from Mar 5 to Mar 6
$153 total
Mar 5 - Mar 6
Total with taxes and fees
Book a stay at this business-friendly affittacamere in Pienza. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Art Studio di Adelina Quadri ...
9.8/10 Exceptional! (51 reviews)
This property has a lovely view, great garden, attentive staff with good breakfast. Stayed in the cottage and the patio was very sunny and relaxing.

Reviewed on Nov 8, 2025

Affitacamere Maria Gabriella
Relais Villa Grazianella - UNA Esperienze

Relais Villa Grazianella - UNA Esperienze

Via Grazianella 5 Montepulciano SI
Fully refundableReserve now, pay when you stay
$197 nightly
The price is $221 total per night from Mar 1 to Mar 2
$221 total
Mar 1 - Mar 2
Total with taxes and fees
Book a stay at this business-friendly country house in Montepulciano. Enjoy free WiFi, free parking, and an attached winery. Our guests praise the helpful staff ...
9.8/10 Exceptional! (279 reviews)
Everything was perfect. Warm welcome, comfortable and spacious rooms, great breakfast. The staff was very kind and friendly. I also recommend the wine tasting experience. Highly recommended!

Reviewed on Dec 5, 2025

Relais Villa Grazianella - UNA Esperienze
Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

5 out of 5
Via Poggio alla Sala 10 Montepulciano SI
Book a stay at this luxury hotel in Montepulciano. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff in our reviews. ...
9.4/10 Exceptional! (123 reviews)
Perfect escape
Fantastic hotel in an incredible setting. Staff were extremely helpful, attentive and understanding. The perfect location for a relaxing break and a centre for exploring Tuscany

Reviewed on Oct 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.
Hotel San Gregorio

Hotel San Gregorio

3 out of 5
Via Della Madonnina 4 Pienza SI
Book a stay at this business-friendly residence in Pienza. Enjoy free WiFi, an outdoor pool, and room service. Popular attractions RI Crea RE and Enoteca Di ...
9.4/10 Exceptional! (134 reviews)
Super convenient location steps to the historic center. Possibly the only hotel with its own dedicated secure / covered parking. Well decorated and breakfast was great!

Reviewed on Oct 25, 2025

Hotel San Gregorio
Casanova - Panoramic Rooms and Suites

Casanova - Panoramic Rooms and Suites

3 out of 5
Strada Provinciale 146 di Chianciano San Quirico d'Orcia SI
Stay at this residence in San Quirico d'Orcia. Enjoy free breakfast, free WiFi, and an outdoor pool. Popular attractions Horti Leonini and Chapel of our Lady ...
Casanova - Panoramic Rooms and Suites
Abbadia Sicille Relais

Abbadia Sicille Relais

4 out of 5
SP 14 Loc. Abbadia Sicille Trequanda SI
Book a stay at this business-friendly residence in Trequanda. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Monastery of Sant'Anna ...
8.8/10 Excellent! (168 reviews)
Room was beyond expectations. Helpful staff and overall great experience.

Reviewed on Dec 7, 2025

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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