Walking and cycling infrastructure and quality open spaces (‘active living infrastructure’) can influence levels of physical activity and related risks of non-communicable disease. Understanding the challenges to creating active living infrastructure could help support the creation of more physically active communities. A qualitative study with nine semi-structured interviews was conducted with ten expert stakeholders purposively sampled across the sectors of urban development, public health and civil society in Jamaica. Thematic analysis found that new active living infrastructure was challenging to provide because it did not fit with widely held views of ‘development’ which focused on road construction, driving and economics, not walking, cycling or nature. Public open spaces were lacking and the few good examples were expensive to maintain, deterring additional investment. Pedestrian infrastructure was poor quality and cycling infrastructure non-existent, making it dangerous for people to walk or cycle which particularly adversely affected people from deprived communities who may lack political voice. Greater collaboration between public health and urban planning, which appeared to be natural allies with shared interests, could help re-frame the multi-sectoral (including economic) benefits of active living infrastructure. Brokers may highlight problems associated with lack of active living infrastructure and also provide contextually relevant examples which go beyond generic international guidance.