Montalcino Travel Guide

Tourist Guide

Montalcino
Montalcino
Montalcino
Montalcino
Montalcino

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.

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 NZ$3,010 per night from 16 Apr to 17 Apr
NZ$3,010
16 Apr - 17 Apr
includes taxes & fees
Stay at this luxury hotel in Montalcino. Enjoy free Wi-Fi, free parking and 2 outdoor pools. Popular attractions Castiglion del Bosco Winery and Corte Pavone ...
10/10 Exceptional! (74 reviews)
Everything was perfect

Reviewed on 25 Mar 2026

Castiglion del Bosco, A Rosewood Hotel
Mastrojanni Relais

Mastrojanni Relais

Localita Loreto e San Pio Montalcino SI
Fully refundableReserve now, pay when you stay
The price is NZ$839 per night from 19 Apr to 20 Apr
NZ$839
19 Apr - 20 Apr
includes taxes & fees
Stay at this business-friendly farm stay in Montalcino. Enjoy free breakfast, free Wi-Fi and free parking. Popular attractions Abbazia di Sant'Antimo and Museum ...
10/10 Exceptional! (65 reviews)
Perfect location and views. Close to Montalcino. Staff went above and beyond.

Reviewed on 9 Mar 2026

Mastrojanni Relais
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 NZ$1,030 per night from 16 Apr to 17 Apr
NZ$1,030
16 Apr - 17 Apr
includes taxes & fees
Stay at this luxury hotel in Montalcino. Enjoy free breakfast, free Wi-Fi and free parking. Popular attractions Abbazia di Sant'Antimo and Museum of Brunello ...
9/10 Wonderful! (341 reviews)
The property was exquisite. The view spectacular and the staff top notch. The indoor and outdoor thermal pools and sauna made our stay very relaxing. The buffet breakfast was amazing.

Reviewed on 11 Nov 2025

Castello di Velona Resort Thermal SPA & Winery
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.
The House of Alice, charm and relaxation

The House of Alice, charm and relaxation

Montalcino (SI) Toscana
Stay at this holiday home in Montalcino. Enjoy a garden, laundry facilities and cable/satellite TV service. Popular attractions Abbazia di Sant'Antimo and Museum ...
9.8/10 Exceptional! (71 reviews)
Lovely charming home and town

Reviewed on 1 Apr 2026

The House of Alice, charm and relaxation
Wonderful new villa in Maremma, near Montalcino and Castiglione della Pescaia

Wonderful new villa in Maremma, near Montalcino and Castiglione della Pescaia

Montalcino Toscana
Stay at this business-friendly villa in Montalcino. Enjoy free Wi-Fi, private pools and daily housekeeping. Popular attractions Tenuta Greppo Franco Biondi Santi ...
9.6/10 Exceptional! (25 reviews)
Privacy and nature
A beautiful house surrounded by nature. Total privacy. Said that the location is quite remote, but excellent for those who look for that.

Reviewed on 25 July 2021

Wonderful new villa in Maremma, near Montalcino and Castiglione della Pescaia
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 Wi-Fi, private pools and a garden. Popular attractions Monastery of Sant'Anna in Camprena and San Giovanni d'Asso ...
10/10 Exceptional! (60 reviews)
Host very helpful. plenty of room inside and out. Beautiful setting.

Reviewed on 17 Nov 2025

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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