Cycling in urban environments provides many benefits to people. However, planning of cycling infrastructures in large cities faces numerous challenges and requires better understanding of both the factors enabling cycling as well as barriers to it, determined by particular local context. While there is a growing body of research that tackle the bike transport related questions in Western Europe and the USA, there is relatively little research on that in Central Eastern Europe (CEE), in post-communist countries. In this study we used qualitative and quantitative methods to explore urban cyclists and non-cyclists opinions about the cycling, the perceived problems and obstacles, and perception of the on-going changes in bicycle transportation system in Warsaw, Poland. Although many people see potential advantages of cycling, it is mostly perceived as a leisure time activity. Those who do utilitarian cycling are more acutely aware of the benefits, such as rapidity and flexibility of this mean of transport. The main perceived barriers are linked to lack of good cycling infrastructure in the city, the feeling of insecurity linked to the behaviour of drivers, and to maintenance during winter. In conclusion, our research highlights both the opportunities and challenges linked to the development of improved cycle transportation system, suggesting the need for a range of policies, from the infrastructure improvements and comprehensive planning of the whole transportation system, to improving the driving culture that would support feeling of security of the cyclists.