Monticchiello Travel Guide

Tourist Guide

Monticchiello which includes a small town or village and heritage architecture as well as an individual female
Monticchiello showing signage
Monticchiello showing flowers and heritage architecture
Monticchiello which includes a small town or village as well as a couple
Monticchiello showing 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 recognised for its close-knit community spirit, summer theatre 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.

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 Wi-Fi and an outdoor pool. Our guests praise the helpful staff in their reviews. Popular attractions ...
8.6/10 Excellent! (577 reviews)
"Loved this hotel - great location. Really quiet despite such a central location. Yes rooms are not super modern but they reflect the history of the building. Great pool and breakfast on the terrace."

Reviewed on 31 Jul 2025

Hotel Relais II Chiostro di Pienza
Nuovo Etruria Resort

Nuovo Etruria Resort

Via di S. Martino snc, Montepulciano, SI
The price is £101 per night from 1 Sept to 2 Sept
£101
per night
1 Sept - 2 Sept
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! (27 reviews)
"Highly recommend it!"

Reviewed on 28 Jul 2025

Nuovo Etruria Resort
Castello di Velona Resort Thermal SPA & Winery

Castello di Velona Resort Thermal SPA & Winery

5 out of 5
Località Velona, Castelnuovo dell'Abate, Montalcino, SI
The price is £605 per night from 11 Aug to 12 Aug
£605
per night
11 Aug - 12 Aug
Stay at this 5-star luxury hotel in Montalcino. Enjoy free breakfast, free Wi-Fi and free parking. Popular attractions Abbazia di Sant'Antimo and Museum of Brunello ...
8.8/10 Excellent! (323 reviews)
"We stayed two nights midway through travelling around Tuscany. It was a lovely peaceful break for us. We felt very pampered by all of the staff who were superb. Dining by the pool area was lovely. A very happy couple of days."

Reviewed on 29 Jul 2025

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.
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 Wi-Fi and an outdoor pool. Popular attractions Horti Leonini and Collegiate ...
9/10 Wonderful! (63 reviews)
"My fiancée and I enjoyed ourselves! It’s a beautiful place and I adored walking around in the nearby town."

Reviewed on 20 Jul 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 Wi-Fi, an outdoor pool and room service. Popular attractions RI Crea RE and Enoteca Di ...
9.2/10 Wonderful! (122 reviews)
"Cozy and welcoming hotel in a perfect location near Pienza’s historic center. I could only stay one night out of three due to personal reasons, but I’ll definitely come back on my next visit"

Reviewed on 3 Aug 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 Wi-Fi, free parking and an outdoor pool. Popular attractions The Saints Peter and Andrew ...
8.8/10 Excellent! (155 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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