The present work examines the case of cross- border cooperation (CBC) between Italy and Slovenia, with particular regard to the construction of town twinning, i.e. territorial integration between Gorizia- Nova Gorizia and Trieste- Koper, in the light of the establishment of broader euroregions. Transboundary regionalization between Italy and Slovenia has become an international model due to the long historical tradition, to the Matrioška model and to the comprehensive approach towards CBC. The borderland can be taken as a paradigmatic example of successful cooperation along the former East- West divide. The SWOT analysis, used in order to assess the strengths, weaknesses, opportunities and threats in the borderland, confirms this hypothesis.