Montalcino

Travel Guide

Montalcino showing a sunset and heritage architecture
Montalcino showing a sunset and heritage architecture
Montalcino which includes landscape views and a sunset
Montalcino featuring 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 kilometers) south from SienaOpens in a new window. Be sure to visit attractions located outside of the town center, 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
$709 nightly
The price is $791 total per night from Aug 26 to Aug 27
$791 total
Aug 26 - Aug 27
Total includes taxes and fees
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! (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 Jul 29, 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
$1,706 nightly
The price is $1,889 total per night from Aug 5 to Aug 6
$1,889 total
Aug 5 - Aug 6
Total includes taxes and 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! (64 reviews)
"Peaceful, Relaxing Stay in Tuscany We had a great experience here. The setting is quiet and secluded—felt like a true escape from everyday life. The golf was excellent, the food was consistently good, and the service was friendly and professional. It is remote, which adds to the charm, but just a ..."

Reviewed on Jun 21, 2025

Rosewood Castiglion del Bosco
SI Montalcino Hotel

SI Montalcino Hotel

3 out of 5
Via Osticcio 21, Montalcino, SI
$147 nightly
The price is $171 total per night from Aug 24 to Aug 25
$171 total
Aug 24 - Aug 25
Total includes taxes and fees
Stay at this 3-star hotel in Montalcino. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions ...
9.2/10 Wonderful! (347 reviews)
"The hotel is in a great location, and our room had a partial view of the sea. The bed, unfortunately, was not as comfortable as I think it could be. It was relatively hard, and we had two double beds, rather than a full-size bed. Service was good as was the breakfast."

Reviewed on Jul 23, 2025

SI Montalcino Hotel
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.
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 ...
9.2/10 Wonderful! (41 reviews)
"What can we say??? Grazie Grazie Grazie! What an amazing week! Camilla went over the top in communication and even helped us arrange a special birthday dinner for my husband with a local cook at the villa ! The pool was fabulous and the air conditioning much appreciated in both bedrooms. Kitchen ..."

Reviewed on Jul 28, 2025

Private and cozy retreat in Montalcino with private pool surrounded by vineyards
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 Jun 10, 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 May 23, 2025

Hilltop house in the heart of Tuscany with private pool
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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