Five years after the publication of the Hamburg Guide, the first of the On the Road series, it was decided to print a new updated version to include recently constructed projects of considerable interest which have been integrated into the five itineraries proposed in the guide. When discussing contemporary architecture, constant updating is a fundamental aspect, especially in those cities intent on maintaining their objectives of high urban planning standards. For this reason, even after only a few years, the first edition ran the risk of being out of date. In 2011 Hamburg was awarded the title of European Green Capital by the European Commission, and almost ten years later, it continues to demonstrate its avant-garde stature in the field of urban development, recovery of decommissioned buildings and brownfield land, development of green urban areas and sustainable mobility. Hamburg has continued to implement its farsighted program which did not cease after the initial changes, but which advanced, creating a network of buildings and infrastructures that confirm the excellent livability levels of German cities. It represents a case study for contemporary designers, because it shows a strategic opportunity for changing and maintaining certain standards that can be used as examples for many European cities currently involved in the adjustments necessary for the change from heavy industry to the green economy. The Niederhafen River Promenade, designed by Zaha Hadid Architects, and opened in 2019, confirmed the city’s aim of evolving according to the criteria of improving the life of its citizens. This promenade, 625 meters long, does not simply form a connection system, but offers new services and possibilities for easy mobility, while reinforcing the protection wall against river flooding. This was obtained while providing Hamburg with an urban landmark able to stand alongside the architectural prestige of the Elbphilharmonie concert hall designed by Herzog & de Meuron, an emblem that demonstrates how contemporary architecture can be layered within the existing fabric to become a symbol for the city. Although they are featured in two separate itineraries, these projects are only a few hundred meters apart, and bear witness to the desire, now successfully accomplished, to redevelop the area of the old port which was in a state of neglect until a few years ago. Alongside the HafenCity workshops and the IBA “new city”, this objective demonstrates how Hamburg was able to reinvent itself beginning with the understanding of its own potential and focusing on new interventions from the viewpoint of sustainable living. Today Hamburg forms an open-air museum for contemporary architecture lovers and an authentic observatory on the realizations and benefits possible with creative sustainable urban planning.