Monticchiello

Travel Guide

Monticchiello featuring a small town or village and heritage architecture as well as an individual female
Monticchiello showing signage
Monticchiello showing heritage architecture and flowers
Monticchiello which includes 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 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 €357 per night from 17 Mar to 18 Mar
€357
includes taxes & fees
17 Mar - 18 Mar
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! (75 reviews)
"Everything and everyone was spot on. Driveway needs repair"

Reviewed on 16 Dec 2024

Precise Tale Poggio Alla Sala
Agriturismo La Sovana
Agriturismo La Sovana
Via di Chiusi 37, Sarteano, SI
The price is €218 per night from 12 Apr to 13 Apr
€218
includes taxes & fees
12 Apr - 13 Apr
Book a stay at this family-friendly farm stay in Sarteano. Enjoy free WiFi, free parking, and an attached winery. Popular attractions Archaeological Museum of ...
9.6/10 Exceptional! (71 reviews)
"This place is stunning. The room is spacious, very clean. Breakfast and dinner were amazing. The owner and family are there making sure we have the best experience possible. Friendly staff. Can’t say enough, love love love my time there."

Reviewed on 9 Oct 2024

Agriturismo La Sovana
Hotel Relais II Chiostro di Pienza
Hotel Relais II Chiostro di Pienza
4 out of 5
Corso Rossellino 26, Pienza, SI
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 ...
8.6/10 Excellent! (544 reviews)
Good stay
"Needed an extra night and got a room through Hotels.com. Was there for a wedding. The room was small but the location was where I wanted to be and the breakfast was very good."

Reviewed on 29 Sep 2024

Hotel Relais II Chiostro di Pienza
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.
Cozy apartment in Monticchiello with Wi-Fi
Cozy apartment in Monticchiello with Wi-Fi
Monticchiello
Stay at this apartment in Pienza. Enjoy cable/satellite TV service, an in-room coffeemaker, and in-room fireplaces. Popular attractions Art Studio di Adelina ...
10/10 Exceptional! (2 reviews)
It's the Little Details...
"This large apartment was incredibly beautiful in so many ways. The owners have done an incredible renovation to modernize the experience without sacrificing the charm you hope to experience in this ancient town. it was clean and the linens were top notch. I think I'll install a towel warmer at home ..."

Reviewed on 17 Dec 2024

Cozy apartment in Monticchiello with Wi-Fi
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 Palazzo Chigi and Horti Leonini ...
9/10 Wonderful! (42 reviews)
"It was a nice property- unfortunate what they charge to just swim"

Reviewed on 26 Oct 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 11 Apr 2024

Hotel San Gregorio
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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