Wineries in Cortona: 10 Wine Tastings and Itineraries between Val d’Orcia and Arezzo
Visiting the wineries in Cortona is one of the most fascinating ways to discover this part of Tuscany. Around the town, vineyards, olive groves and historic estates tell the story of a landscape where wine is deeply rooted in local culture and traditions.
Cortona is also an excellent starting point for a wine journey through eastern Tuscany. Within a day, you can visit the wineries of the Cortona DOC wine region, explore the Orcia DOC wineries in Val d’Orcia, or head towards Arezzo and the vineyards of the Arezzo Chianti hills.
Staying at Monastero San Silvestro, in the countryside just outside Cortona, makes it easy to dedicate each day to a different wine region.
We have selected 10 wineries between Cortona, Val d’Orcia and Arezzo, organizing them into three wine itineraries combining tastings, Tuscan landscapes, historic villages and art cities.
1. Wineries in Cortona and the Surrounding Area: Discovering Syrah
When it comes to wine in Cortona, one grape variety deserves special attention: Syrah.
Although originally from France, Syrah has found particularly favorable growing conditions in the hills around Cortona. Today, approximately 80% of Cortona DOC production is associated with this grape variety.
The Consorzio Vini Cortona, established in 2000, brings together around 60 producers and protects an appellation that includes Syrah, Sangiovese and several other wine styles.
For travelers looking for wineries and wine tastings near Cortona, these three estates are particularly worth discovering.
Fabrizio Dionisio
Among the wineries to visit around Cortona, Fabrizio Dionisio is an excellent choice for anyone interested in understanding the close relationship between this territory and Syrah.
The estate is located in the Cortona countryside, in the Il Sodo area, and includes approximately 15 hectares of vineyards spread across different plots. Syrah plays a central role in the winery’s production and is expressed through several labels, offering visitors an opportunity to discover how the same grape variety can change according to vineyard, vintage and winemaking choices.
Among its most representative wines are Il Castagno, a Cortona Syrah DOC made exclusively from Syrah grapes grown in the vineyard of the same name, and Cuculaia, another important expression of the estate’s Syrah.
Alongside its red wines, the winery also produces Castagnino, a rosé made from Syrah grapes and a different, more immediate way to discover Cortona’s signature variety.
Visiting Fabrizio Dionisio therefore means stepping directly into the contemporary story of Syrah in Cortona, comparing different expressions of a grape that has found one of its most distinctive Italian terroirs in these Tuscan hills.
Tenimenti d’Alessandro
Located in Manzano, in the Cortona countryside, Tenimenti d’Alessandro is closely connected with the modern history of Syrah in this part of Tuscany.
Since the late 1980s, the estate has carried out extensive experimentation to identify the grape varieties best suited to the local terroir, focusing particularly on Syrah and Viognier.
Today, the property includes approximately 30 hectares of certified organic vineyards.
Wine enthusiasts may also find it interesting that, since 2018, the estate has voluntarily chosen to market its wines as Toscana IGT rather than Cortona DOC, while continuing to produce them in the hills of Cortona.
Wine experiences include a visit to the historic cellar and different tasting options featuring four to six wines accompanied by local products.
Stefano Amerighi
Among the producers who best illustrate the relationship between Cortona and Syrah is Stefano Amerighi, currently president of the Consorzio Vini Cortona.
His winery is particularly suitable for visitors who want to explore the signature wine of the area and discover an estate strongly focused on vineyard work and the identity of Cortona Syrah.
Including Amerighi in a Cortona wine itinerary is also an opportunity to understand how the same grape variety can develop different characteristics depending on the vineyard, soil and winemaking choices.
Cortona Wine Itinerary: A Day between Wineries and the Historic Centre
Monastero San Silvestro → Fabrizio Dionisio → Cortona → Tenimenti d’Alessandro o Stefano Amerighi → Monastero San Silvestro
Start the morning with a winery visit and wine tasting near Cortona, then head up to the historic centre and spend a few hours exploring the town.
After lunch, return to the Cortona countryside for a second winery visit.
Il consiglio è di limitarsi a due degustazioni nella stessa giornata: in questo modo rimane il tempo per godersi Cortona e, soprattutto, per vivere le cantine senza fretta.
This is the ideal itinerary for anyone who wants to discover Cortona Syrah and understand why this grape variety has become one of the symbols of the local wine region.
2. Wineries in Val d’Orcia: Wine Tastings near Pienza and Orcia DOC
Heading from Cortona towards Pienza, the landscape gradually changes.
The hills become broader, white country roads appear among farms and rows of cypress trees, and the unmistakable scenery of Val d’Orcia begins to unfold.
The wine changes too.
The Orcia DOC appellation was established in 2000 and covers twelve municipalities, including Pienza, San Quirico d’Orcia and Trequanda. Sangiovese is the leading grape variety: Orcia DOC wines must contain at least 60% Sangiovese, while Orcia Sangiovese requires a minimum of 90%.
For travelers staying in Cortona, spending a day visiting the wineries of Val d’Orcia offers the opportunity to compare this wine region with the Syrah-focused territory around Cortona.
Capitoni
Near Pienza, Capitoni retains the intimate character of a family-run farm, where a wine tasting becomes above all an opportunity to meet the people who actually make the wine.
A visit can include a walk through the vineyards followed by time in the cellar, where current vintages are tasted. Upon request, visitors may also have the opportunity to taste older vintages or wines still ageing, drawn directly from the barrels.
It is an ideal stop for anyone looking for a wine tasting near Pienza with a personal atmosphere, away from more standardized wine-tour experiences.
Visits are available by reservation.
Fabbrica Pienza
Fabbrica Pienza offers a more contemporary interpretation of the Val d’Orcia wine scene.
Experiences range from a simple tasting at the wine shop to a complete tour through the vineyards and cellar, followed by a tasting of five wines and extra virgin olive oil.
At certain times of the year, visitors can also combine the wine tour with a picnic among the vineyards or a light lunch.
This is an especially appealing option for travelers who want to turn a winery visit into a genuine half-day wine experience in Val d’Orcia.
Podere Albiano
Moving towards Petroio and Trequanda, you will find Podere Albiano, located within the Orcia DOC production area.
Here, Sangiovese once again takes centre stage, both as a single-variety wine and in interpretations where it is blended with other grape varieties.
Its location makes this winery particularly interesting for travelers looking to create a less crowded itinerary away from the most famous tourist routes in Val d’Orcia.
After the tasting, continue towards Petroio, a village historically associated with terracotta production, or towards Trequanda.
Val d’Orcia Wine Itinerary: Pienza, Wineries and Tuscan Villages
Monastero San Silvestro → Pienza → Capitoni → Fabbrica Pienza → Monticchiello → Monastero San Silvestro
Leaving Cortona in the morning, the first destination is Pienza.
You can schedule a wine tasting at Capitoni before spending a few hours exploring Pienza’s historic centre, perhaps stopping for lunch to taste the town’s famous Pecorino di Pienza cheese.
In the afternoon, continue to Fabbrica Pienza for a second winery experience.
Before returning to Cortona, a detour to Monticchiello offers the perfect way to end the day while enjoying one of the most beautiful landscapes in Val d’Orcia.
Travelers who prefer a more rural route can instead head towards Podere Albiano, Petroio and Trequanda.
3. Wineries near Arezzo and in the Arezzo Chianti Hills
The third wine itinerary starts in Cortona and follows the Val di Chiana towards Arezzo.
This route is particularly interesting because it makes it easy to combine a wine tasting near Arezzo with a visit to one of Tuscany’s most important art cities.
In the countryside around Arezzo, Sangiovese and the traditions of Chianti coexist with Syrah, Cabernet Franc, Merlot, Vermentino and other grape varieties.
Here are four wineries to consider.
Villa La Ripa
In the hills of Antria, just outside Arezzo, Villa La Ripa combines wine, olive oil, history and landscape.
The property is surrounded by vineyards and olive groves in the Arezzo Chianti hills and centres around an elegant Renaissance villa.
The wine tour takes visitors through the vineyards and cellar and ends with a tasting of four wines accompanied by cured meats, cheeses, Tuscan bread and the estate’s extra virgin olive oil.
It is one of the most complete winery experiences to include in a day trip to Arezzo, combining wine with a particularly attractive historical and scenic setting.
Buccia Nera
In the Campriano area, Buccia Nera is an organic winery in the countryside around Arezzo.
Its tasting experiences introduce visitors to both the vineyards and the cellar. Some options include a guided tour followed by a wine tasting with bread and olive oil, with the possibility of adding other traditional local products.
It is an interesting stop for anyone wishing to learn more about the relationship between organic farming and winemaking in Tuscany.
Fattoria Il Muro
Just outside the city, Fattoria Il Muro represents another expression of the winemaking tradition of the Arezzo countryside.
Traditional Tuscan grape varieties grow alongside international varieties in the estate’s vineyards, providing an interesting comparison between different interpretations of the local terroir.
Its convenient location close to Arezzo makes the winery easy to combine with a visit to the historic centre.
Tenuta di Frassineto
Along the route connecting Cortona and Arezzo, Tenuta di Frassineto is one of the easiest winery stops to include in a day trip.
Tours may include the vineyards, the modern winery and the old cellar, now used for barrel ageing.
The most complete experience also includes a walk through the park surrounding the 19th-century villa and a tasting of four wines accompanied by Tuscan specialties.
The estate’s production also provides an opportunity to discover several different grape varieties, from Vermentino and Syrah to Cabernet Franc and Sangiovese.
Arezzo Wine Itinerary: Wineries, Art and the Historic Centre
Monastero San Silvestro → Tenuta di Frassineto → Arezzo → Villa La Ripa → Monastero San Silvestro
Start the day with a visit to Tenuta di Frassineto, taking advantage of its convenient position along the route between Cortona and Arezzo.
Continue towards the historic centre of Arezzo, where it is worth spending a few hours exploring Piazza Grande, the Basilica of San Francesco and the streets of the old town.
After lunch, head towards the hills of Antria and end the day with a wine tasting at Villa La Ripa.
Alternatively, for a second day dedicated to the Arezzo wine region, choose Buccia Nera and Fattoria Il Muro.
This itinerary offers an excellent combination of Tuscan wine, art, history and countryside.
10 Wineries to Visit between Cortona, Val d’Orcia and Arezzo
Our selection covers three different wine regions.
Wineries in Cortona and the surrounding area: Fabrizio Dionisio, Tenimenti d’Alessandro and Stefano Amerighi.
Wineries in Val d’Orcia: Capitoni, Fabbrica Pienza and Podere Albiano.
Wineries in Arezzo and the surrounding area: Villa La Ripa, Buccia Nera, Fattoria Il Muro and Tenuta di Frassineto.
These ten wineries make it possible to create a journey through three different expressions of Tuscan wine: Cortona Syrah, Sangiovese and Orcia DOC wines in Val d’Orcia, and finally the wines produced in the hills around Arezzo and the Arezzo Chianti area.
There is no need to visit all ten wineries during the same stay. In fact, the best way to enjoy these experiences is to choose one or two wineries per day, book wine tastings in advance, and leave enough time to explore Tuscany’s historic villages, towns and landscapes along the way.
