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Bucket list experience:

Last updated: 08 November, 2022
Expert travel writer: Nicky Swallow

This beautiful 3-hour walk leads through farmland and vineyards (this is Brunello wine country), passing old farmhouses and tiny stone hamlets that seem caught in a time warp.

It begins in the lovely old town of Montalcino, famous for its production of red Brunello wines. There is only a short stretch on an asphalt road; otherwise, there is no traffic, just eyefuls of glorious scenery and a feeling of being very much away from it all. The route finishes at the ravishing abbey of Sant’Antimo, where, if you are lucky, you can hear the resident monks singing Gregorian chant at evensong.

Price: Free
Minimum age: Any
Age suitable: 13+
When: All year around
Duration: 3 hours

Getting there & doing it

The walk starts in Montalcino near the southwest tip of the Fortezza, along Via del Poggiolo, which soon turns into a country path. The route passes along rough country tracks, through woods, along panoramic hillsides with only a short stretch on asphalted road. There’s a certain amount of uphill walking involved, but nothing too strenuous.

Past the half-way mark, the route meets the charming 13th-century hamlet of Villa a Tolli. Soon after this, the abbey of Sant’Antimo comes into view below, set among olive trees and vineyards. The route is well-marked, but a local walking map is recommended.

It’s best to start in Montalcino and catch a local bus back from Sant’Antimo, so you need to time the walk to coincide with the bus times (the last one leaves at around 5pm and there is no service on Sundays). You can also arrange a taxi service in Montalcino: ask in the tourist office for details. They can also supply maps.

When to do it

The route is accessible all year; in summer you are likely to have quite a lot of company along the way, but in winter it’s quite possible not to see another soul for the whole route. In July and August, it’s advisable to avoid the hottest hours of the day; start first thing in the morning or in the late afternoon.

Our writer’s picks of the best places to stay near this experience, closest first

Hotel Rosewood Castiglion del Bosco

Montalcino, Tuscany, Italy[6.2 miles]

An impeccable country hotel set on a huge working wine estate, Castiglion del Bosco offers luxurious accommodation in one of the most beautiful corners of Tuscany.

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Adler Spa Resort Thermae

San Quirico d'Orcia, Tuscany, Italy[11.4 miles]

One of the best thermal spa resorts in Tuscany, surrounded by the glorious Val d’Orcia, with superb facilities including a huge indoor-outdoor pool complex with waters heated to a natural 37°C.

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Agriturismo Il Rigo

Casabianca, Tuscany, Italy[12.2 miles]

A long-established agriturismo located in a glorious setting just outside lovely old San Quirico in the Val d’Orica. A working organic farm run by the ninth generation of a family.

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Montepulciano, Tuscany, Italy[22.5 miles]

A beautiful, stylishly-restored 17th-century farmhouse complex is a romantic retreat for couples or those looking for an intimate, authentic place to stay.

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Destination guides including or relevant to this experience


Tuscany, Italy

The astonishingly beautiful region of Tuscany has it all: art cities and ancient hill towns, high mountains and long sandy beaches, alongside luxurious hotels and some of Italy’s best food and wine.

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Our writer’s recommendations of other bucket list experiences our writer says you must do in this destination, closest first

A day in the Val d’Orcia

Val d'Orcia, Tuscany, Italy[16.2 miles]

One of the most beautiful areas of Tuscany, the Val d’Orcia is a ravishing expanse of open, undulating farmland, dotted by atmospheric hill towns and dominated by Monte Amiata, an extinct volcano.

Best for ages: 18+ | Free

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Other worthwhile experiences near this experience if you have time or interest..

panorama of the Brunello wine lands in the spring with hills covered with soft green grass in the town of Montalcino

Montalcino Wine Region

Montalcino, Tuscany, Italy[0.7 miles]

Known for its highly-prized (and often expensive) DOCG Brunello wine, Montalcino is one of the most famous wine-growing areas in Tuscany. Many of the local wine estates are open for tastings; among the best are Casato Primedonne, Casanova di Neri, Biondi Santi Tenuta Greppo and Castello di Banfi. Visits must be booked in advance.

Best for ages: 18+ | Free

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Abbey of Sant’Antimo

Abbey of Sant’Antimo

Castelnuovo dell'Abate, Tuscany, Italy[6.5 miles]

The beautiful Benedictine abbey of Sant’Antimo lies in open countryside close to Montalcino and dates from the 8th century; the resident monks sing Gregorian chants each evening.

Best for ages: 18+ | Free

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