Depressa: Castle History, Olive Mill and Winery

If you are looking for hotels in Depressa, the town’s history can help you get a clearer sense of the destination. The town brings together a medieval castle core, buildings with their own dates, an underground olive mill and a historic winery. It is also situated on the slopes of the Serre di Andrano and Castiglione. Its themes range from family history and architecture to traditional olive processing and winemaking, offering different ways to assess Depressa as a travel destination.

Castle and Family History

The oldest core of Castello di Depressa dates back to the 14th century. The museum in the basement of Castello di Depressa documents the history of the Winspeare family and their ancestors, costumes and traditions. This brings two historical layers together: the age of the castle core and the family history to which the museum is dedicated.

Buildings and Their Historical Contexts

The Calvario di Depressa was built in 1885. On April 15, 1973, it was restored with five sculptural ceramic panels. The Croce di Principano is located on the left side of the road from Depressa to Castiglione, a hamlet of Andrano, in the fief known as “di Principano.”

At the Cupola di Simone Murat, the focus is on its purpose and construction. According to a local historical account, the French oenologist Simone Murat built it as a place to rest after work. The cupola is designed in the Neoclassical style and made entirely of Lecce stone.

Palazzo Winspeare can be seen from Piazza Castello in Depressa. A local architecture report from 2019 described it as a historic building that had recently been restored at the time. Largo dei Pozzi Messapici comprises 15 small, well-like structures that provide access to underground cavities. Access conditions may have changed; before visiting, check whether the cavities are currently accessible and whether access is safe.

Landscape, Olive Oil and Wine

Depressa lies on the slopes of the Serre di Andrano and Castiglione. The Grotta dei Municeddhri is an underground olive mill. Olives were fed through an opening in the ceiling directly onto a millstone to produce oil.

At Castel di Salve, the family history continues into the present: Antonio Winspeare founded the historic winery in 1885; today, the fourth and fifth generations of the Winspeare family run the business. 1885 is also the year the Calvario was built, but the date refers here to two different events: the construction of the building and the founding of the winery. The Festa della “Simeddha” adds a specific culinary connection: its third edition was held on July 19, 2025, in Piazza Castello in Depressa.

The dates are not all equally precise: the oldest core of the castle dates back to the 14th century, the Grotta was probably built around 1400, while the Calvario is associated with both 1885 as its construction year and April 15, 1973 as its restoration date. This places an approximate construction period alongside specific historical dates.

Discover more destinations: Monteroni Di Lecce, Leverano, Lequile, Copertino, Conca Specchiulla, Lizzanello, Martano, Porto Badisco.

For the broader travel overview: Lecce.