Monticchiello Travel Guide

Tourist Guide

Monticchiello showing heritage architecture and a small town or village as well as an individual female
Monticchiello which includes signage
Monticchiello showing flowers and heritage architecture
Monticchiello which includes a small town or village as well as a couple
Monticchiello featuring 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
The price is AU$826 per night from 3 Aug to 4 Aug
AU$826
3 Aug - 4 Aug
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! (96 reviews)
"*"

Reviewed on 5 Jul. 2025

Precise Tale Poggio Alla Sala
Nuovo Etruria Resort
Nuovo Etruria Resort
Via di S. Martino snc, Montepulciano, SI
The price is AU$215 per night from 9 July to 10 July
AU$215
9 July - 10 July
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! (16 reviews)
"The room was very clean. The view from the room is stunning! It is very quiet and relaxing. The resort is facing Montepulciano! The staff is very nice and friendly. I highly recommend it."

Reviewed on 14 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! (568 reviews)
Great Town, not so great hotel
"The hotel it's ok It's a former Franciscan Convent dating back to 13th century! Depending of the room.it will be room size. The best views you will get from the outside terrace where breakfast it's served Amazing views of Toscana The hotel it's located right in the middle of the town Pienza right ..."

Reviewed on 29 Jun. 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 residence in San Quirico d'Orcia. Enjoy free breakfast, free WiFi, and an outdoor pool. Popular attractions Horti Leonini and Collegiate ...
9/10 Wonderful! (60 reviews)
"The property was lovely but a little dated. Beakfast was good but never on time to open Beds were not comfortable but scenery is nice and good restaurant right next door is convienent."

Reviewed on 20 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! (116 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
Il Tosco
Il Tosco
Via del Poliziano 13, Montepulciano, SI
Book a stay at this luxury residence in Montepulciano. Enjoy free WiFi, free parking, and room service. Popular attractions Medici Fortress and Torre del Pulcinella ...
10/10 Exceptional! (109 reviews)
"If we had to return to one place in all of Italy, we’d choose Il Tosco. It was absolutely SPECTACULAR! Elena was the most wonderful hostess, providing many recommendations, of which every one was spot on! The breakfast was out of this world - better than any place we’ve ever stayed. Kitchen was stocked ..."

Reviewed on 17 Jun. 2025

Il Tosco
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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