Monticchiello

Travel Guide

Monticchiello
Monticchiello
Monticchiello
Monticchiello
Monticchiello

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.

Affitacamere Maria Gabriella

Affitacamere Maria Gabriella

Via Marino Cappelli, 6 Pienza SI
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! (56 reviews)
"We were looking to be close to Pienza, instead we discovered a treasure in Montechiello! We cannot say enough about how serene and beautiful this stay was!"

Reviewed on May 16, 2026

Affitacamere Maria Gabriella
Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

5 out of 5
Via Poggio alla Sala 10 Montepulciano SI
$391 nightly
The price is $437 total per night from Jun 7 to Jun 8
$437 total
Jun 7 - Jun 8
Total with taxes and fees
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. ...
9.6/10 Exceptional! (137 reviews)
"Beautiful stay for our honeymoon. This is definitely a place to go and feel at peace in the Tuscan countryside. 15 min away from some wineries and 20 min away from Montepulciano. Great balance of feeling relaxed by the spa and pool with some quick getaways. Lastly, the restaurant was beyond excellent. ..."

Reviewed on May 23, 2026

Precise Tale Poggio Alla Sala
Castello di Velona Resort Thermal SPA & Winery

Castello di Velona Resort Thermal SPA & Winery

5 out of 5
Località Velona Montalcino SI
$689 nightly
The price is $769 total per night from Jun 17 to Jun 18
$769 total
Jun 17 - Jun 18
Total with taxes and fees
Book a stay at this luxury hotel in Montalcino. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Abbazia di Sant'Antimo and Museum of Brunello ...
9/10 Wonderful! (349 reviews)
"I cant think of a more perfect place to stay. It is a beautiful property, with a long history, in one of the most beautiful regions of the world. We had one of the more "basic" rooms but it was still luxurious and comfortable. Amenities were great and the food/wine was amazing. We had some logistical ..."

Reviewed on May 16, 2026

Castello di Velona Resort Thermal SPA & Winery
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! (143 reviews)
"Nice hotel - clean, good breakfast, perfect location. Would stay again!"

Reviewed on May 5, 2026

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 ...
9.2/10 Wonderful! (86 reviews)
"Everything was great"

Reviewed on May 16, 2026

Casanova - Panoramic Rooms and Suites
Corte Francigena - Apartments

Corte Francigena - Apartments

Via Ferretti Montalcino SI
Stay at this apartment in Montalcino. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Abbazia di Sant'Antimo and Museum of Brunello ...
9.8/10 Exceptional! (6 reviews)
"Very beautiful quiet village. Wouldn’t recommend going without having some form of transportation. Pretty secluded area but thats why we chose it."

Reviewed on Sep 22, 2024

Corte Francigena - Apartments
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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