Monticchiello

Travel Guide

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

Breathtaking natural landscapes, a storybook medieval quarter and community theatre 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 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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Hotel Relais II Chiostro di Pienza

4 out of 5
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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 ...
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Reviewed on 25 Aug 2025

Hotel Relais II Chiostro di Pienza
Hotel Panoramic

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3 out of 5
Via di Villa Bianca, 8, Montepulciano, SI
The price is HK$250 per night from 10 Oct to 11 Oct
HK$250
HK$908 total
10 Oct - 11 Oct
includes taxes & fees
Stay at this 3-star family-friendly hotel in Montepulciano. Enjoy an outdoor pool, a rooftop terrace, and room service. Popular attractions Terme di Montepulciano ...
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Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

5 out of 5
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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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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.
Casanova - Panoramic Rooms and Suites

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3 out of 5
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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 2 Sept 2025

Casanova - Panoramic Rooms and Suites
Hotel San Gregorio

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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 ...
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Pienza getaway
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Reviewed on 1 Sept 2025

Hotel San Gregorio
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Private and cozy retreat in Montalcino with private pool surrounded by vineyards

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Book a stay at this family-friendly villa in Montalcino. Enjoy private pools, a garden, and laundry facilities. Popular attractions Castello Banfi and Corte ...
9.2/10 Wonderful! (43 reviews)
"Views were spectacular, property as it looked on the website. Beautiful stone converted barn (I think), comfortable outdoor seeding and eating area to make use of the views. Kitchen was small but functional. Any problems were dealt with quickly by Camilla and her caretaker the efficient Romeo. Only ..."

Reviewed on 1 Sept 2025

Private and cozy retreat in Montalcino with private pool surrounded by vineyards
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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