Monticchiello

Travel Guide

Monticchiello which includes a small town or village and heritage architecture as well as an individual female
Monticchiello showing signage
Monticchiello which includes heritage architecture and flowers
Monticchiello showing 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 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.

Relais Villa Grazianella - UNA Esperienze

Relais Villa Grazianella - UNA Esperienze

Via Grazianella 5 Montepulciano SI
The price is HK$1,149 per night from 18 Dec to 19 Dec
HK$1,149
HK$1,301 total
18 Dec - 19 Dec
includes taxes & fees
Stay at this business-friendly country house in Montepulciano. Enjoy free Wi-Fi, free parking and an on-site winery. Our guests praise the helpful staff in their ...
9.6/10 Exceptional! (278 reviews)
Everything was perfect. Warm welcome, comfortable and spacious rooms, great breakfast. The staff was very kind and friendly. I also recommend the wine tasting experience. Highly recommended!

Reviewed on 5 Dec 2025

Relais Villa Grazianella - UNA Esperienze
Grand Hotel Admiral Palace

Grand Hotel Admiral Palace

4 out of 5
Via Umbria 2 Chianciano Terme SI
The price is HK$690 per night from 7 Jan to 8 Jan
HK$690
HK$795 total
7 Jan - 8 Jan 2026
includes taxes & fees
Stay at this spa hotel in Chianciano Terme. Enjoy free breakfast, free Wi-Fi and free parking. Popular attractions Piazza Italia and Terme di Chianciano are ...
8/10 Very Good! (303 reviews)
The staff was very helpful and nice. Safe neighborhood and quiet.

Reviewed on 29 Jun 2025

Grand Hotel Admiral Palace
Fonteverde Lifestyle & Thermal Retreat

Fonteverde Lifestyle & Thermal Retreat

5 out of 5
Localita Terme, 1 San Casciano dei Bagni SI
The price is HK$2,731 per night from 6 Jan to 7 Jan
HK$2,731
HK$3,041 total
6 Jan - 7 Jan 2026
includes taxes & fees
Stay at this luxury hotel in San Casciano dei Bagni. Enjoy free breakfast, free Wi-Fi and free parking. Popular attractions Fonteverde Terme and Pasticceria ...
9.2/10 Wonderful! (179 reviews)
Best resort I’ve ever stayed in! So clean, bathroom is refreshing, the many thermal pools, the views, I’ll be going back every year.

Reviewed on 25 Oct 2025

Fonteverde Lifestyle & Thermal Retreat
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.
Hotel San Gregorio

Hotel San Gregorio

3 out of 5
Via Della Madonnina 4 Pienza SI
Stay at this business-friendly residence in Pienza. Enjoy free Wi-Fi, an outdoor pool and room service. Popular attractions RI Crea RE and Enoteca Di Ghino are ...
9.2/10 Wonderful! (134 reviews)
Super convenient location steps to the historic center. Possibly the only hotel with its own dedicated secure / covered parking. Well decorated and breakfast was great!

Reviewed on 25 Oct 2025

Hotel San Gregorio
Abbadia Sicille Relais

Abbadia Sicille Relais

4 out of 5
SP 14 Loc. Abbadia Sicille Trequanda SI
Stay at this business-friendly residence in Trequanda. Enjoy free Wi-Fi, free parking and an outdoor pool. Popular attractions Monastery of Sant'Anna in Camprena ...
8.8/10 Excellent! (162 reviews)
Room was beyond expectations. Helpful staff and overall great experience.

Reviewed on 7 Dec 2025

Abbadia Sicille Relais
Private and cozy retreat in Montalcino with private pool surrounded by vineyards

Private and cozy retreat in Montalcino with private pool surrounded by vineyards

Siena Tuscany
Stay at this family-friendly villa in Montalcino. Enjoy private pools, a garden and laundry facilities. Popular attractions Castello Banfi and Corte Pavone Winery ...
9.4/10 Exceptional! (48 reviews)
Probably the highlight of our 5 week vacation through Europe. We spent 5 wonderful days here relaxing by the pool and enjoying the commanding views. Camilla was a gracious and quick responding host. Would love to come back!

Reviewed on 22 Oct 2025

Private and cozy retreat in Montalcino with private pool surrounded by vineyards
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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