Monticchiello

Travel Guide

Monticchiello showing a small town or village and heritage architecture as well as an individual female
Monticchiello featuring signage
Monticchiello which includes 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 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 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
Fully refundableReserve now, pay when you stay
The price is S$627 per night from 28 Jun to 29 Jun
S$627
28 Jun - 29 Jun
includes taxes & fees
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. ...
9.2/10 Wonderful! (91 reviews)
"Overall"

Reviewed on 6 Jun, 2025

Precise Tale Poggio Alla Sala
Nuovo Etruria Resort
Nuovo Etruria Resort
Via di S. Martino snc, Montepulciano, SI
The price is S$137 per night from 22 Jun to 23 Jun
S$137
22 Jun - 23 Jun
includes taxes & fees
Stay at this hotel in Montepulciano. Enjoy an outdoor pool, breakfast (surcharge), and daily housekeeping. Popular attractions Church of St. Agnes and Colonna ...
9.2/10 Wonderful! (9 reviews)
"The place is well located , with lovely view of the old city walls. The room was specious, very clean , nice breakfast and great assistance and service of the front desk with reservation problem we had .. thanks for everything"

Reviewed on 5 Jun, 2025

Nuovo Etruria Resort
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! (560 reviews)
"Beautiful hotel in a beautifully preserved town centre. Bags of atmosphere and history and generous service and breakfasts. The hotel is in the pedestrianised old town so vehicle access and parking is not catered for. The upside however is its central location and access to local amenities on foot ..."

Reviewed on 30 May, 2025

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.
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! (55 reviews)
"We had a beautiful view from the balcony and the room was nice. The bathroom was well renovated. We had a very nice dinner at the restaurant and they catered for gluten free. The only criticism i have is the swimming cap rule also applies to the spa and we felt like it wouldn't be as relaxing so ..."

Reviewed on 11 Jun, 2025

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! (113 reviews)
"Fabulous location just outside the entrance to the main part of town. Property is stylish in an olde worlde way, perfect for relaxation."

Reviewed on 18 Apr, 2025

Hotel San Gregorio
Abbadia Sicille Relais
Abbadia Sicille Relais
4 out of 5
SP 14 Loc. Abbadia Sicille, Trequanda, SI
Stay at this 4-star business-friendly residence in Trequanda. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions The Saints Peter and Andrew ...
8.8/10 Excellent! (154 reviews)
An amazing find. Would love to return
"An amazing place with a luxury feel. Comfy, welcoming and peacefully relaxing"

Reviewed on 30 Nov, 2024

Abbadia Sicille Relais
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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