Montalcino

Travel Guide

Montalcino which includes heritage architecture and a sunset
Montalcino which includes a sunset and heritage architecture
Montalcino featuring landscape views and a sunset
Montalcino which includes outdoor eating and a sunset
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 HK$9,425 per night from 16 Nov to 17 Nov
HK$9,425
HK$10,457 total
16 Nov - 17 Nov
includes taxes & fees
Stay at this 5-star luxury hotel in Montalcino. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attractions Castiglion del Bosco Winery and Corte ...
10/10 Exceptional! (67 reviews)
Beautiful property and great service. Was a little disappointed they charge double the price for wine they make in their back yard then I pay here in Montreal.

Reviewed on 3 Aug 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, Castelnuovo dell'Abate, Montalcino, SI
Stay at this 5-star luxury hotel in Montalcino. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Abbazia di Sant'Antimo and Museum of Brunello ...
8.8/10 Excellent! (333 reviews)
Everything was 5 star. It’s like living in a castle in the sky with hot thermal pools everywhere and amazing food. We loved our outdoor patio with the sunset view of the panorama.

Reviewed on 26 Oct 2025

Castello di Velona Resort Thermal SPA & Winery
Mastrojanni Relais

Mastrojanni Relais

Localita Loreto e San Pio, Castelnuovo dell'Abate, Montalcino, SI
The price is HK$3,103 per night from 26 Nov to 27 Nov
HK$3,103
HK$3,503 total
26 Nov - 27 Nov
includes taxes & fees
Book a stay at this business-friendly farm stay in Montalcino. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Abbazia di Sant'Antimo ...
9.8/10 Exceptional! (59 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.
Villa in Montalcino, exclusive for you, stunning view!!!

Villa in Montalcino, exclusive for you, stunning view!!!

Montalcino
Stay at this villa in Montalcino. Enjoy free WiFi, private pools, and a garden. Popular attractions San Giovanni d'Asso Station and Museo del Tartufo are located ...
10/10 Exceptional! (69 reviews)
The pool area was awesome, very clean and beautiful landscape.Beds were comfortable, house was very clean! Loved the little coffee room.Lots of space to spread out in.Luigi was an excellent host!

Reviewed on 13 Oct 2025

Villa in Montalcino, exclusive for you, stunning view!!!
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
Book a stay at this family-friendly villa in Montalcino. Enjoy private pools, a garden, and laundry facilities. Popular attractions Castello Banfi and Corte ...
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
The House of Alice, charm and relaxation

The House of Alice, charm and relaxation

Montalcino (SI)
Stay at this vacation home in Montalcino. Enjoy a garden, laundry facilities, and cable/satellite TV service. Popular attractions Abbazia di Sant'Antimo and ...
9.6/10 Exceptional! (66 reviews)
Check in process was seamless as our host was watching for our arrival. The accommodations were an absolute dream located in the wall of the city with updated interior. Just gorgeous!

Reviewed on 28 Sept 2025

The House of Alice, charm and relaxation
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

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Top destination
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3/5 - Okay

Verified traveller

We checked In to a lovely hotel 30 mins away.