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Tuscany’s best kept secret

Discover one of Tuscany’s most picturesque areas, with rolling landscapes, pleasant medieval towns and some of the finest food and wine in the region.

One of seven UNESCO World Heritage Sites in Tuscany, the Val d’Orcia’s sweeping landscape is a paradise for walkers, cyclists, hikers as well as wine and food lovers. Its deep green valleys are filled with vineyards producing some of the region’s finest wines, including Brunello di Montalcino and Nobile di Montepulciano. Located south of Siena, the area is arguably the most visually impressive and romantic area of Tuscany, the setting for a fairy tale.

The valley has long been an enchanted getaway for Italians and foreign travellers alike looking for the charm of towns like Montalcino, Pienza, and Montepulciano, for the renowned cuisine and wine, and for its convenient location between Florence and Rome, both are less than a two-hour drive away.

Not to be missed


In the past, Montepulciano winemakers would roll finished barrels uphill to their estates in town for ageing. A few of these producers, who still use their historic cellars in town, are open for visitors and offer wine tasting in their cantine. Apart from the wine, the town is an open-air museum with different form of art lining its streets. Take a stroll along its picturesque alleys and enjoy a café in Piazza Grande for the perfect vantage point to watch life go by.

Views from Piazza San Francesco in Montepulciano


Park outside the medieval walls and wander at random down streets with names like Via del Bacio, “street of the kiss.” Note the Renaissance perfection of Rossellino’s orderly Piazza Pio II and enjoy a tour of the Cathedral and the Palazzo Piccolomini with its hanging gardens. Shop for handmade pottery and visit the many boutiques selling different varieties of delicious pecorino cheeses, both young and aged.


A fundamental stop for wine lovers, Montalcino’s territory will astound with the quality, beauty, and character of its two hundred vineyards, all arranged in sixteen square kilometres around a hill, at the top of which sits the town of Montalcino. The pristine streets and astounding views make Montalcino a worthy stop on any tour of Tuscany. A perfect way to complete the trip is with a visit to the austere Romanesque Abbey Sant’Antimo, just ten kilometres downhill from Montalcino.

Sant'Antimo's Abbey near Montalcino

Essenza’s top tips

If you are not tied to vacationing in the summer months, try the Val d’Orcia in Autumn: as the tourist season winds down, vineyards turn to russet and gold, and harvest festivals abound.

Make sure you visit a winery or two to learn all about winemaking in Tuscany and sample some of the best wines of the region, usually accompanied by delicious cured meat, bruschetta and locally produced extra virgin olive oil.

Make sure you have at least one day free of planned activities so you can go back to places you loved and simply wander around at your own pace.

Further Reading


Florence's "Wine Windows"

A Whimsical Tale of Tuscany's Vinous Legacy


Italian Culinary Symphony

Essenza's guide to gastronomic adventures and dining etiquette


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