Doha, the capital of Qatar, used to be a port town on the eastern part of the peninsula of Qatar. Historically, the town shared cultural commonalities with other Gulf cities, particularly relying on fishing and pearl diving as the main feature of its economy. The old town, which was characterised by compact urbanism, extended families living in courtyard houses and shaded allies, was totally abandoned after the oil discovery and the flow of unprecedented financial resources in the late ‘70s and early ‘80s. This paper provides a critical narrative of the urban regeneration process that took place in the heart of Doha. It interrogates the new vision that was articulated to revitalise the old heart of the city and bring people back to such a valuable part of its urban fabric. The paper examines the Design Strategies used in the project to move from adaptive reuse to holistic urban regeneration. It analyses the use of oil and Gas revenues to help the city go beyond the western illusions and urban spectacle, and argues that the project is a manifestation of a needed transformation from the urbanity of an image to the urbanity of meaning. Such city transformation is essential for constructing a more dynamic and vibrant identity for the city.