A prototype of a Smart Bike (CloudBike ) was developed under the VeloCity project. CloudBike sets up an infrastructure, services and CloudBike Kits for cyclists in different user contexts and scenarios, such as: secure city cycling; cycling for wellbeing; digital social innovation campaigns for gathering user-generated data (UGD); etc. The CloudBike digital ecosystem consists of: 1) a cloud based infrastructure for collecting and processing data; 2) the cyclist’s smartphone/tablet/PDA (computing and sensing device) with a mountable breakdown protecting and water-proof transparent case, and different sets of intelligent wearable sensors; 3) a mobile app that exploits both open data and UGD for provision of different (context based) services (including eCall). CloudBike will make possible implementation of comprehensive (bike-inclusive, user-centred) multimodal Smart City transportation systems and marketable products based on reuse of open data and UGD. The user interface will be very simplified: well readable text; maps; speech via a headset; speech generated information: navigation, messages, alerts; a pair of physical buttons to alternate a short list of (pre-programmed) modes of functionality. A few pilot trials were organised in Bulgaria, Italy and Spain.