Montalcino

Travel Guide

A historic tower with arches and a bell, surrounded by traditional buildings with tiled roofs and satellite dishes.
A stone house with a tiled roof surrounded by lush greenery and trees.
A cobblestone street lined with outdoor cafes, wooden shutters, and hanging lights.
A wooden sign with grape illustrations and the text "Grapho blu" against a backdrop of a historic building and a scenic view.
A narrow street lined with outdoor cafes and restaurants, with people dining and walking.

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 Montalcino SI
The price is CA $1,059 per night from Sep 27 to Sep 28
CA $1,059
CA $1,181 total
Sep 27 - Sep 28
includes taxes & fees
Book a stay at this luxury hotel in Montalcino. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Abbazia di Sant'Antimo and Museum of Brunello ...
9/10 Wonderful! (370 reviews)
"Staying here was a wonderful and truly unique experience. The only reason I’m giving it 4 stars instead of 5 was because of the challenges we had with the air conditioning in our room. That said, the staff really did make an effort to find a workaround for us. While it wasn’t a perfect solution, ..."

Reviewed on Sep 9, 2026

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

Castiglion del Bosco, A Rosewood Hotel

5 out of 5
Localita Castiglion del Bosco Montalcino SI
The price is CA $3,291 per night from Oct 8 to Oct 9
CA $3,291
CA $3,636 total
Oct 8 - Oct 9
includes taxes & fees
Book a stay at this luxury hotel in Montalcino. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attractions Castiglion del Bosco Winery and Corte ...
10/10 Exceptional! (81 reviews)
"Very warm and friendly service."

Reviewed on Sep 13, 2026

Castiglion del Bosco, A Rosewood Hotel
Mastrojanni Relais - Small Luxury Hotels of the World

Mastrojanni Relais - Small Luxury Hotels of the World

Localita Loreto e San Pio Montalcino SI
The price is CA $833 per night from Oct 4 to Oct 5
CA $833
CA $932 total
Oct 4 - Oct 5
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! (78 reviews)
"Perfect, pristine, could not be any better!"

Reviewed on Aug 6, 2026

Mastrojanni Relais - Small Luxury Hotels of the World
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.
Corte Francigena - Apartments

Corte Francigena - Apartments

Via Ferretti Montalcino SI
Stay at this apartment in Montalcino. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Abbazia di Sant'Antimo and Museum of Brunello ...
Corte Francigena - Apartments
Palazzo Saloni

Palazzo Saloni

Via Soccorso Saloni 31 Montalcino SI
Book a stay at this luxury aparthotel in Montalcino. Enjoy free breakfast, free parking, and an attached winery. Popular attractions Fortress of Montalcino and ...
Palazzo Saloni
Montalcino: Private villa in the heart of Tuscany, private pool, A/C

Montalcino: Private villa in the heart of Tuscany, private pool, A/C

Montisi Tuscany
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! (65 reviews)
"Fijne plek om vakantie te vieren met een jong gezin. Ligging is ook praktisch voor bezoeken aan de dorpen en steden in de buurt."

Reviewed on Aug 13, 2026

Montalcino: Private villa in the heart of Tuscany, private pool, A/C
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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