This book examines the impacts of tourism-led transformations on the industrial historical waterfront at Darling Harbour and The Rocks in Sydney, Australia in the context of urban restructuring and deindustrialisation. The book also offers an extended reflection on the paradoxes between tourism and heritage. This discussion is not a new concept. However, this book critically explores the significance of the industrial heritage assets of these areas and the implications of the transformation procedures. Although Darling Harbour and The Rocks have generally been considered success stories of transformation with mixed touristic, recreational, residential and commercial activities, this book examines and evaluates how industrial history and heritage values have been affected. It demonstrates that tourism/leisure-led developments create urban landscapes in which cultural identity and historical assets are sacrificed and/or reinvented.