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! (62 reviews)
"A fantastic stay in such a beautiful part of Tuscany. Hosts were friendly and went out of their way to help. Breakfast was lovely and the room was clean and comfortable. Would highly recommend!"

Reviewed on Jun 15, 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
$553 nightly
The price is $615 total per night from Jul 11 to Jul 12
$615 total
Jul 11 - Jul 12
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! (146 reviews)
"It’s a beautiful property, but be aware that it is secluded and that the restaurant menu is quite limited and after a couple of days, we were happy to go elsewhere. The waiting staff was attentive and nice, front desk not as much (maybe the la guard barrier?)"

Reviewed on Jun 19, 2026

Precise Tale Poggio Alla Sala
Nuovo Etruria Resort

Nuovo Etruria Resort

Via di S. Martino snc Montepulciano SI
$105 nightly
The price is $120 total per night from Jun 21 to Jun 22
$120 total
Jun 21 - Jun 22
Total with taxes and fees
Stay at this hotel in Montepulciano. Enjoy an outdoor pool, breakfast (surcharge), and daily housekeeping. Popular attractions Colonna del Marzocco and Palazzo ...
9.4/10 Exceptional! (96 reviews)
"Very friendly staff. Beautiful property."

Reviewed on Jun 19, 2026

Nuovo Etruria Resort
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 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! (91 reviews)
"Everything was great"

Reviewed on May 16, 2026

Casanova - Panoramic Rooms and Suites
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! (147 reviews)
"The hotel was beautiful maintained and a very convenient location. We stayed in a newly renovated room which was quite modern and clean with excellent spaces for clothes and toiletries which I appreciated! Our room didn’t have a view, it looked onto another building which I was a bit disappointed ..."

Reviewed on Jun 15, 2026

Hotel San Gregorio
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 Castello Banfi and Abbazia di Sant'Antimo are ...
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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