Montalcino Travel Guide

Tourist Guide

Montalcino which includes heritage architecture and a sunset
Montalcino showing 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.

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! (324 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
Rosewood Castiglion del Bosco

Rosewood Castiglion del Bosco

5 out of 5
Localita Castiglion del Bosco, Montalcino, SI
The price is NZ$3,772 per night from 19 Aug to 20 Aug
NZ$3,772
19 Aug - 20 Aug
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! (65 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
Mastrojanni Relais

Mastrojanni Relais

Localita Loreto e San Pio, Castelnuovo dell'Abate, Montalcino, SI
Fully refundableReserve now, pay when you stay
The price is NZ$824 per night from 12 Sept to 13 Sept
NZ$824
12 Sept - 13 Sept
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! (49 reviews)
"This is such a wonderful hotel in the middle of the country to forget about everything and immerse into the real Tuscany. The food in the restaurant is excellent, their Manager Stefano is such a great guy and makes you feel as part of the family, his dog is adorable and all the staff is just incredible! ..."

Reviewed on 31 Jul. 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! (67 reviews)
"Lovely villa in a beautiful location."

Reviewed on 10 Jun. 2025

Villa in Montalcino, exclusive for you, stunning view!!!
Hilltop house in the heart of Tuscany with private pool

Hilltop house in the heart of Tuscany with private pool

Montisi
Stay at this villa in Montalcino. Enjoy free WiFi, private pools, and a garden. Popular attractions San Giovanni d'Asso Station and The Saints Peter and Andrew ...
9.8/10 Exceptional! (61 reviews)
Tuscany retreat
"Wonderful, quiet, beautiful. Everything you could want in country stay near a small village."

Reviewed on 23 May 2025

Hilltop house in the heart of Tuscany with private pool
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! (61 reviews)
Beautiful townhouse in a quaint village
"We loved our stay at the house of Alice. It is a beautifully decorated townhouse with plenty of space for 4 people. The village it’s in is so nice too, with great views.Only comment is that laundry isn’t in the unit. You can pay to have it done for you though."

Reviewed on 30 Jun. 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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