Levels of cycling for transport (CFT) in Ireland are very low—about 2% nationally—and the government has set a target of 10% of all trips to work by bicycle by 2020. The purpose of this study was to explore the complexities of leisure/sport cyclists’ views about CFT. Sixteen leisure/sport cyclists (four women and 12 men; about half cycled for transport) were interviewed about the factors that influenced their decision to cycle somewhere instead of driving and the role of the weather in that decision, whether they considered CFT to be real “exercise,” and the meaning of “safety.” The findings were that the decision to cycle for transport was dominated by practical concerns, and weather concerns added to this organizational burden. For city-dwellers, the key deciding factor was cycling’s efficiency and reliability. Safety concerns centered around negative interactions with drivers and there was a common belief that the general public had very negative attitudes to cycling and cyclists. Finally, most thought that CFT was not “proper” exercise as it would be of insufficient intensity or duration and would take from the time available to do this. These findings show that to promote CFT among leisure/sport cyclists, government and local authorities must improve and highlight the efficiency, safety, and legitimacy of cycling as a transport option. Without this, promotional activities that just focus on the exercise, health, and enjoyment potential of CFT will have little effect.