Monticchiello

Travel Guide

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
Monticchiello featuring heritage architecture and flowers
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.

Precise Tale Poggio Alla Sala
Precise Tale Poggio Alla Sala
5 out of 5
Via Poggio alla Sala 10, Montepulciano, SI
The price is ¥48,641 per night from Mar 30 to Mar 31
¥48,641
¥54,479 total
includes taxes & fees
Mar 30 - Mar 31
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. ...
9.4/10 Exceptional! (76 reviews)
"Absolutely beautiful property with very friendly and helpful staff. They really took care of us during our short stay"

Reviewed on Mar 20, 2025

Precise Tale Poggio Alla Sala
Relais Villa Grazianella - UNA Esperienze
Relais Villa Grazianella - UNA Esperienze
Via Grazianella 5, Via delle tre berte, Montepulciano, SI
The price is ¥28,763 per night from Mar 31 to Apr 1
¥28,763
¥32,288 total
includes taxes & fees
Mar 31 - Apr 1
Book a stay at this business-friendly country house in Montepulciano. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff ...
9.6/10 Exceptional! (214 reviews)
Great location…exceptional service
"Stunning property with stunning views. The room was exceptional…large comfortable beds. But the views! The restaurant downstairs was one of the best I’ve ever experienced, and I once lived in Italy for 11 years. The Ragu was best ever. The hosts and staff were friendly and did everything possible ..."

Reviewed on Mar 20, 2025

Relais Villa Grazianella - UNA Esperienze
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, SI
The price is ¥26,387 per night from Apr 1 to Apr 2
¥26,387
¥29,674 total
includes taxes & fees
Apr 1 - Apr 2
Stay at this 3-star spa residence in San Quirico d'Orcia. Enjoy free breakfast, free WiFi, and an outdoor pool. Popular attractions Horti Leonini and Collegiate ...
9/10 Wonderful! (42 reviews)
"It was a nice property- unfortunate what they charge to just swim"

Reviewed on Oct 26, 2024

Casanova - Panoramic Rooms and Suites
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.
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, SI
Stay at this 3-star spa residence in San Quirico d'Orcia. Enjoy free breakfast, free WiFi, and an outdoor pool. Popular attractions Horti Leonini and Collegiate ...
9/10 Wonderful! (42 reviews)
"It was a nice property- unfortunate what they charge to just swim"

Reviewed on Oct 26, 2024

Casanova - Panoramic Rooms and Suites
Hotel San Gregorio
Hotel San Gregorio
3 out of 5
Via Della Madonnina 4, Pienza, SI
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! (111 reviews)
"Very nice staff, great service, super clean. Will stay again."

Reviewed on Apr 11, 2024

Hotel San Gregorio
Farmhouse in the greenery of the Tuscany countryside with private pool and view
Farmhouse in the greenery of the Tuscany countryside with private pool and view
Murlo
Stay at this vacation home in Murlo. Enjoy free WiFi, private pools, and a garden. Popular attractions Castello di Montepescini and Castiglion del Bosco Winery ...
9.4/10 Exceptional! (41 reviews)
Off the Beaten Path
"This property is several kilometers up a gravel road from Murlo, Italy. The road is okay but we got a little concerned after it had been raining for a while. The property is remote and near several hiking paths. It is great for people who want to get out and hike around the hills of Italy. The gardens ..."

Reviewed on Oct 14, 2024

Farmhouse in the greenery of the Tuscany countryside with private pool and view
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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