For more than a decade, hundreds of experts have gathered at the hills overlooking Florence to analyse the evolution of European transport policy and regulation at the call of the Florence School of Regulation (FSR). This book reflects the discussions in Florence, and more broadly, it documents the evolution of transport regulation in the European Union. The purpose of this book is to share the knowledge we at FSR Transport have built as privileged observers by bringing to the forefront the most interesting pieces in our “Observers”. In particular, we have selected the more relevant valuative pieces opening our Observers over the last decade whilst organising them according to the topic they address in four different blocks. We open with the rail block, as rail was the original topic of most of our Forums. Aviation has also received a lot of our attention, and in particular, Air Traffic Management and the Single European Sky, which in turn, have their own dedicated sub-block. We close with a block on intermodality, which has drawn increasing attention. The texts have not been edited for the book other than minor temporal references to improve readability. We have included as opening pieces our “Manifesto for the Next Five Years of EU Regulation of Transport”, published in November 2019 ahead of the start of the von der Leyen Commission’s mandate, and an update for a post-COVID-19 recovery, published in June 2020. In these documents, a more comprehensive vision of the challenges in EU transport regulation is provided.