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Reconciling heritage conservation and development within the management of historic urban environments is recognised as one of the most challenging issues in the field of heritage conservation and urban management by academics and practioners. Existing urban heritage conservation policies, regulatory frameworks and tools operating around the world proved to be inadequate or insufficient in regulating urban transformations in historic urban environments. The "heritage versus development dilemma" has been a central argument in the 21 st international discourse on urban heritage conservation management and development. UNESCO, the United Nations, ICOMOS and the Council of Europe have tried to overcome this persisting dichotomy through the adoption of a series of international texts. The evolution of a 21 st century international discourse represents the international recognition that a "new paradigm for urban heritage conservation and management" has gradually taken shape since the beginning of the century. From this moment, urban heritage conservation can be seen as an all- encompassing, integrated urban management strategy, which incorporates the perspectives of urban planning and socio-economic development. The contemporary approach suggests moving beyond existing regulatory and management frameworks, recommending a revision of local practices so that they are consistent with the key principles of the new paradigm. However, there is still a need to carry out further research in order to understand how existing and consolidated urban management systems currently operate. This is a fundamental step towards effectively implementing the new paradigm into local practices. This interdisciplinary study aims to advance knowledge in the field of urban heritage conservation and management through a detailed assessment of the level of consistency of existing policies with the key principles of the 21 st century approach. To the knowledge of the author, this is the first comprehensive and comparative assessment of multi-scalar (at national, regional, provincial and local levels) and multi-sectorial (including heritage conservation, urban planning and socio-economic development) urban management policies that has been carried out so far. To conduct this study, an original assessment framework was developed by the author with the objective of providing a qualitative evaluation tool which was able to link the international theory with local practices. The thesis focused on the two World Heritage cities of Florence (Italy) and Edinburgh (UK). It systematically demonstrated how some of the key principles of the new paradigm are already integrated into local urban management policies of these two historic urban environments. The study was first conducted by testing the assessment framework on the two case studies. Subsequently, a critical analysis of the two urban management systems was carried out, integrating the assessment results with data collected through semi-structured interviews with local stakeholders involved in the definition and implementation of the assessed policies. Finally, a comparison of Florence and Edinburgh's approaches to urban heritage conservation, management and development were illustrated and discussed. In this way, it was possible to discuss the strengths and weaknesses, opportunities and threats of different urban management systems in incorporating a 21 st century international approach. Moreover, the study identified existing similarities and discrepancies between different approaches and to highlight good practices and critical aspects. The research findings constitute a step towards understanding whether a revision of existing policies and tools is necessary and how this could be done. The assessment results could be used by national and local governments to revise their current urban management policies according to the contemporary international approach to urban heritage conservation, management and development.