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In the idyllic landscape, towns are few and far between, but they make up for it with their fascinating character. The medieval settlement of Vipavski Križ, an erstwhile town, boasts a castle and a monastery which was built a few years later. The settlement is the most exceptional cultural monument of the Vipava Valley. This picturesque settlement is carefully restored and never ceases to amaze with the myriad of intricate architectural details.

Unlike Vipavski Križ, Vipava never had town privileges, although its medieval centre interestingly displays many urban design elements. Reigning supreme on the lovely main square is the Baroque Lanthieri Mansion. The bridges over the springs of the Vipava River are an eye-catcher, and the fortified settlement of Tabor never ceases to amaze newcomers.

The town of Ajdovščina, today the centre of the Upper Vipava Valley, grew from the foundations of the Antique settlement within a Roman fort. The old town centre that for centuries stayed within the safety of the wall is a maze of narrow alleys. The well-maintained residences of wealthy families from the 18th and 19th century are a testament to an era of economic prosperity.  

The youngest town of the Vipava Valley and Slovenia, Nova Gorica, has a particularly noteworthy architectural design. When in the aftermath of the Second World War the town of Gorica stayed in Italy, Yugoslavia commissioned the construction of a new town from scratch right next to the border. The town plan was designed by the Slovenian architect Edvard Ravnikar who was a student of Jože Plečnik and Le Corbusier.