Montalcino

Travel Guide

Montalcino featuring a sunset and heritage architecture
Montalcino which includes a sunset and heritage architecture
Montalcino showing a sunset and landscape views
Montalcino featuring a sunset and outdoor eating
Montalcino featuring 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.

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 €1,090 per night from 21 Mar to 22 Mar
€1,090
21 Mar - 22 Mar
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 ...
Castiglion del Bosco, A Rosewood Hotel
Mastrojanni Relais

Mastrojanni Relais

Localita Loreto e San Pio Montalcino SI
The price is €411 per night from 29 Mar to 30 Mar
€411
29 Mar - 30 Mar
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! (64 reviews)
Perfect location and views. Close to Montalcino. Staff went above and beyond.

Reviewed on 9 Mar 2026

Mastrojanni Relais
SI Montalcino Hotel

SI Montalcino Hotel

3 out of 5
Via Osticcio 21 Montalcino SI
Stay at this hotel in Montalcino. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff in their reviews. Popular attractions ...
9.2/10 Wonderful! (377 reviews)
Beautiful ground, good breakfast, not much service,

Reviewed on 12 Nov 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.
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 Jul 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
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 Tuscany
Stay at this family-friendly villa in Montalcino. Enjoy private pools, a garden and laundry facilities. Popular attractions Castello Banfi and Corte Pavone Winery ...
9.4/10 Exceptional! (67 reviews)
Probably the highlight of our 5 week vacation through Europe. We spent 5 wonderful days here relaxing by the pool and enjoying the commanding views. Camilla was a gracious and quick responding host. Would love to come back!

Reviewed on 22 Oct 2025

Private and cozy retreat in Montalcino with private pool surrounded by vineyards
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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Reviews of Montalcino

4
Top destination
5 - Excellent
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4 - Good
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3 - Okay
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2 - Disappointing
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3/5 - Okay

Verified traveller

We checked In to a lovely hotel 30 mins away.