It’s hard not to fall for the seductive charms of Tuscany. Rolling vineyards and evergreen oak forests, shimmering olive groves, stretching cypresses in the setting sun, echoes of the Renaissance, abundant fresh produce and hearty cuisine, endless espressos, sprezzatura, aperitivo, Negroni. Then there are the wines, the many prized vintages that are unique to this delightful part of Italy. But where should your wine adventure begin?

Since the sheer volume of excellent wining and dining Tuscan style can be a touch overwhelming, we’re concentrating on the micro region of Val d’Orcia, where the enchanting hills of medieval Montalcino produce the celebrated Brunello and Super Tuscan.

We have gathered a list of some of the finest vineyards and restaurants, recommending areas to explore and places to stay which combined will make an ideal base for you to design your own personal wine trail.

One of Italy’s star wine regions, Val d’Orcia produces the prized 100 percent Sangiovese red wines — the oak-aged Brunello di Montalcino DOCG and younger Rosso di Montalcino DOC. The pleasant, warm climate in this part of central Italy, shielded from the harsh elements by Monte Amiata, and with just enough breeze from the nearby sea, is ideal for cultivating the grape.

Argiano

One of the oldest estates in the region, and set in beautiful grounds surrounding the Renaissance-style Villa Bell’Aria, the Montalcino winery is certified organic thanks to the innovative soil-mapping project initiated by the new owner. The vineyard’s 2016 Brunello di Montalcino Vigna del Suolo was named “Red Wine of the Year” for 2022.

Frescobaldi

With a story that spans some 700 years and with 30 generations of passionate winemakers, Frescobaldi is one of the oldest and most celebrated winemaking dynasties in Italy, pioneering modern wine production in Tuscany, and introducing new grape varieties, Chardonnay, Cabernet and Merlot, to the region.

Salvioni

The boutique Montalcino winery is run by the Salvioni family where they produce wines through artisan methods to include the Salvioni Brunello di Montalcino. The estate’s small volumes enjoy a great reputation around the world.

Siro Pacenti

A relatively young winery, the estate was founded by 1970 when Siro Pacenti purchased a property north of Montalcino in the area of Pelagrilli and proceeded to plant vines. Today the estate is run by Giancarlo Pacenti producing a revered Brunello di Montalcino and Riserva.

Le Ragnaie

Set in some of the highest vineyards around Montalcino, Le Ragnaie winery and agriturismo was established in 2003 when the Campinoti family bought the property from a family who made rustic wines. Now run by Riccardo Campinoti, the estate produces some of the most prized Brunello di Montalcino wines in the region.

From elegant villas to vineyard hotels, and rustic farmhouses, the traveler will be spoiled for choice in the region of Val d’Orcia and surrounding Tuscany.

Argiano Dimore

Set in the winery surrounding Villa Bell’Aria, guest accommodation is in the original complex of country houses, replete with a dedicated chef whose seasonal menu is based on fresh, local ingredients. Naturally, the estate’s wines are served at tableside.

Castiglion del Bosco

The luxurious resort and village is entirely dedicated to wine. Owned by the Ferragamo fashion family, it has its own winery, hotel and luxury suites, villas, multiple restaurants, gardens, spas and all the trimmings.

La Bandita Townhouse / Countryhouse

Created by the former music mogul John Voigtmann, the exceptionally stylish La Bandita Townhouse and rural Countryhouse boutique hotels offer an experience akin to Soho House of Tuscany.

Mastrojanni

Relais Mastrojanni is nestled in the hills of southern Tuscany. Under the Illy Group, the place has undergone architectural renovations, the ancient walls of the farmhouse housing the Relais have carefully been restored with elegant simplicity with all rooms enjoying splendid views of the Val d’Orcia and of the Mastrojanni vineyards.

Il Cocceto

The restored 18th century farmhouse is architecturally designed and perfect for those seeking a private accommodation.

Le Ragnaie

The relaxed rustic farmhouse also comes with a forward-thinking winery.

Here you will find the finest Tuscan produce: fresh vegetables, delicious breads, cheeses and meats, delicate local honey and aromatic olive oil. Try the thick Ribollita soup, Pici all’Aglione, Cacio e Pepe with Pecorino di Pienza, and Zuppa di Pane — cucina povera at its simple best.

Trattoria Il Pozzo

Set in the medieval village of Sant'Angelo in Colle, this intimate and welcoming place serves authentic and genuine Tuscan dishes.

Acquacheta

A popular destination for locals and tourists, the osteria makes arguably the finest Bistecca alla Fiorentina, the local t-bone steak, in Montepulciano.

Osteria Le Logge

Argiano's CEO and winemaker Bernardino Sani’s getaway in Siena, the venue offers fine cuisine and a cosmopolitan environment where intellectuals, politicians, artists, food lovers and visitors gather.

Osticcio

A modern interpretation of Tuscan cuisine, the place has a superb wine cellar, and offers exceptional views onto the Val d’Orcia countryside.

Podere Il Casale

Eating with pleasure is pivotal to the experience here, with the produce grown organically at the farm or sourced locally, while guests can learn the recipes at the on-site cooking school.

Trattoria Osena

Specializing in traditional Tuscan cooking, the restaurant is regarded for its homemade Pici pasta and wild boar ragu.

The Val d’Orcia region may claim to enjoy some of Tuscany’s loveliest landscapes, but it is also a great spot from which to explore this part of central Italy’s historic cities, namely Siena.

Montalcino

The charming medieval walled hill town has panoramic vistas over the Val d’Orcia. Spend time here enjoying the very best enotecas and restaurants serving world-class wines and regional foods.

Siena

The Renaissance city will transport you back to the Middle Ages with its incredible art and architecture. Siena shares some of the best produce sourced from southern Tuscany to be enjoyed in local trattorias, osterias and restaurants.

Pienza

With panoramic views of the Val d’Orcia, the tiny village is coveted for its Pecorino Pienza, so essential for Pici with Cacio e Pepe: a must-try dish. Pienza is also considered one of the best examples of Renaissance town planning.

Montepulciano

On the fringe of the Val d’Orcia, a visit is a must for tasting the famous Vino Nobile di Montepulciano enjoyed with delicious Tuscan delicacies, while soaking up the charming atmosphere of this Renaissance town. 

Bagno Vignoni

This ultimate spa village dates back to Roman times and is built around natural thermal spas.

ARGIANO'S CEO AND WINEMAKER, BERNARDINO SANI, SHARES HIS SECRET VAL D’ORCIA

Where would a visitor experience authentic local food?

Trattoria Il Pozzo in Sant'Angelo in Colle, Val d'Elsa. Also, try our own fabulous restaurant at the Argiano estate where our chef makes seasonal dishes using local produce.

Where do you like to eat?

Le Logge or Taverna del Capitano, both in Siena.

And for a special occasion?

Arnolfo in Colle, Val d'Elsa

Other than Argiano, where would you recommend a wine lover to stay?

Castiglion del Bosco resort, Mastrojanni resort, or Casanova de Neri resort.

Where should someone visit when they come to the region?

The Val d'Orcia is unique in its mix of nature, art and food. Visit Pienza, Montepulciano and Bagno Vignoni Terme and, of course, Siena.