The initiatives of cycling infrastructure enhancements around the world reveal a consistent interest in promoting cycling to transition toward sustainable lifestyles and safe multi-modal commuting. Accordingly, proposals for cyber-physical systems for smart cycling are also growing, providing solutions to make cycling a safer and better experience for cyclists. However, most existent solutions address single cyclist problems rather than group cycling issues. It is evident that further work is needed to improve safety and comfort for groups of cyclists traveling on busy urban bicycle paths or dedicated bicycle highways. In this paper, we position the concept of technology-assisted cooperative cycling. We introduce a platoon-based cyclist cooperative system that provides safe and efficient coordination for groups of cyclists. We present the results of an experimental prototype tested on real cyclists as well as comprehensive simulations that test the performance of our solution in different scenarios. We demonstrate that our system is feasible to implement and tolerates the human error factor while it is still able to achieve a constant spacing policy. Coordinated platoons of bicycles can be extremely useful to maximize the positive impact of green waves of traffic lights for cyclists and can be extended to groups of two-wheeled vehicles, including mopeds and self-balanced electric vehicles.