Montalcino

Travel Guide

Montalcino featuring a sunset and heritage architecture
Montalcino featuring a sunset and heritage architecture
Montalcino featuring landscape views and a sunset
Montalcino showing a sunset and outdoor eating
Montalcino which includes signage

Famous for its viniculture, this hilltop town also has a walled old town decorated with a majestic fortress, churches and piazzas.

Wine enthusiasts, history buffs and nature lovers flock to the picturesque town of Montalcino. Perched on a hill above Tuscany’s Val d’Orcia, the town boasts a stimulating mix of enoteche (wine stores), ancient monuments and museums. First settled around A.D. 800, Montalcino grew into a medieval stronghold and later achieved worldwide fame for its production of Brunello di Montalcino wine.

The crisscrossing streets and staircases of the wall-enclosed historic quarter are ideal to explore on foot. Start your visit at Fortezza di Montalcino (aka Rocca), a huge fortress built in the 1300s. Enjoy views of the surrounding valleys, vineyards and orchards from the tower and ramparts. Sample local wines at the fortress’s own enoteca.

Follow the streets down from the fortress to Piazza del Popolo. Here you’ll find architectural treasures such as the arched Loggia and the town hall, Palazzo dei Priori. Nearby is the Chiesa di Sant’Agostino and Montalcino Cathedral, notable for its Corinthian-style entrance and collection of antique art.

Spot more art, such as exhibitions of 14th- and 15th-century works by Sienese masters, at the Civic and Diocesan Museum of Sacred Art.

Vying for space with the town’s historic buildings are the enoteche and osteria (taverns). Take time out from sightseeing and treat yourself to a flight of Brunello di Montalcino wines. Alternatively, watch the world go from a café terrace while sipping on a coffee.

A great time to visit is in July, when the town is in full festival swing. The Jazz and Wine Festival takes over the fortress with live concerts and the Festival della Val d’Orcia hosts dance and theatrical performances.

Montalcino is about 25 miles (40 kilometres) south from SienaOpens in a new window. Be sure to visit attractions located outside of the town centre, including the 8th-century Sant’Antimo Abbey. Stop off on the way at the Brunello Museum to learn about the town’s winemaking history.

Ideal for daytrips and weekend breaks, Montalcino is also a great base for exploring the Val d’Orcia. Relax in the thermal baths in Bagni San FilippoOpens in a new window or go hiking and skiing at Mount Amiata.

Rosewood Castiglion del Bosco

Rosewood Castiglion del Bosco

5 out of 5
Localita Castiglion del Bosco Montalcino SI
The price is RM5,205 per night from 3 Jan to 4 Jan
RM5,205
RM5,774 total
3 Jan - 4 Jan 2026
includes taxes & fees
Stay at this luxury hotel in Montalcino. Enjoy free Wi-Fi, free parking and 2 outdoor pools. Popular attractions Castiglion del Bosco Winery and Corte Pavone ...
10/10 Exceptional! (69 reviews)
Wonderful stay

Reviewed on 25 Nov 2025

Rosewood Castiglion del Bosco
Castello di Velona Resort Thermal SPA & Winery

Castello di Velona Resort Thermal SPA & Winery

5 out of 5
Località Velona Montalcino SI
Stay at this 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! (337 reviews)
The property was exquisite. The view spectacular and the staff top notch. The indoor and outdoor thermal pools and sauna made our stay very relaxing. The buffet breakfast was amazing.

Reviewed on 11 Nov 2025

Castello di Velona Resort Thermal SPA & Winery
Mastrojanni Relais

Mastrojanni Relais

Localita Loreto e San Pio Montalcino SI
The price is RM1,550 per night from 21 Dec to 22 Dec
RM1,550
RM1,754 total
21 Dec - 22 Dec
includes taxes & fees
Stay at this business-friendly farm stay in Montalcino. Enjoy free breakfast, free Wi-Fi and free parking. Popular attractions Abbazia di Sant'Antimo and Museum ...
9.8/10 Exceptional! (60 reviews)
The staff was outstanding and the meals were amazing, i.e., fresh, wholesome, and homemade. The chef’s team was very creative with the dinner menu which featured a stellar selection fish, pasta and vegetables grown on the premises. Room was impeccable. Highly recommend a stay at Mastrojanni.

Reviewed on 2 Oct 2025

Mastrojanni 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.
Antico Brunello

Antico Brunello

Argiano Sant'Angelo in Colle Montalcino SI
Stay at this villa in Montalcino. Enjoy horse riding on-site, air conditioning and an outdoor pool. Popular attractions Castello Banfi and Poggio Antico are ...
Antico Brunello
ApartHotel Anghel

ApartHotel Anghel

via Paolo Frajese 71 Siena SI
Stay at this business-friendly apartment in Siena. Enjoy free Wi-Fi, free parking and laundry facilities. Popular attractions Santa Maria della Scala and National ...
8.2/10 Very Good! (325 reviews)
Would recommend staying here and will hopefully be back!

Reviewed on 17 Oct 2025

ApartHotel Anghel
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
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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Reviews of Montalcino

4
Top destination
5 - Excellent
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4 - Good
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4 - Good 0%
3 - Okay
1
3 - Okay 50%
2 - Disappointing
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3/5 - Okay

Verified traveller

We checked In to a lovely hotel 30 mins away.