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 Siena. 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 Filippo or go hiking and skiing at Mount Amiata.

Known for

Wineries, Adventure and Historical Buildings

Top Hotels in Montalcino

Estimated price for 1 night / 2 adults
Image for Castello di Velona Resort, Thermal Spa & Winery
Castello di Velona Resort, Thermal Spa & Winery
5 out of 5
Località Velona, Montalcino
4.6/5Wonderful! (219 reviews)

"Everything was beautiful.....room, service, dining, facilities and scenery. Truly a wonderful taste of Tuscany. Highly recommended and a highlight of our visit to Italy."…"

Reviewed on Jun 24, 2019

Castello di Velona Resort, Thermal Spa & Winery
Image for Rosewood Castiglion del Bosco
Rosewood Castiglion del Bosco
5 out of 5
Localita Castiglion Del Bosco, Montalcino
$1,029/night
Aug 1 - Aug 2
4.9/5Exceptional! (15 reviews)

"Amazing property - staff were always so helpful and our 2 year old loved the heated pool."…"

Reviewed on Apr 29, 2019

Rosewood Castiglion del Bosco
Image for Agriturismo Le Ragnaie
Agriturismo Le Ragnaie
Localita Le Ragnaie, Montalcino
$97/night
Jul 31 - Aug 1
4.6/5Wonderful! (224 reviews)

"The room and property was clean and relaxing. The staff were helpful but have limited hours onsite. The breakfast was delicious. I enjoyed the wine tasting onsite. No laundry on site so you will have to drag your laundry into town if needed."…"

Reviewed on Jul 1, 2019

Agriturismo Le Ragnaie

Popular things to do in Montalcino

Piazza del Campo
Image for Piazza del Campo

Piazza del Campo

Learn more about the local history when you visit Piazza del Campo, a well-known historical site in Siena. Discover the area's beautiful countryside, or seek out its local tours.

Siena Cathedral
Image for Siena Cathedral

Siena Cathedral

Learn more about the local history when you visit Siena Cathedral, a well-known historical site in Siena. Discover the beautiful countryside while you're in the area.

Pienza Cathedral
Image for Pienza Cathedral

Pienza Cathedral

Admire the arresting Renaissance façade and the interior Gothic décor of this 15th-century cathedral commissioned by Pope Pius II.