Concerning the increase in the number of trips and tourists after the COVID-19 pandemic, TSPs (Transport Service Providers) and transport organizations are trying to improve their operability to answer the needs and expectations of passengers. This paper presents a methodology to assess and evaluate to what extent innovative technologies meet the needs of tourists and TSPs involved in the digital ecosystem for door-to-door trips in Europe, making railways and public transport more attractive and consequently encouraging people to use more intermodal solutions in public transport. In this study, two kinds of quantitative data are used: operational KPIs (Key Performance Indicators) and USI (User Satisfaction Index) surveys. The Effectiveness concept, as a metric of the capacity to meet these needs and expectations by the innovative technology, is calculated by merging both types of quantitative data. The method considers tourists’ socio-demographic profiles, allowing comparisons among TSPs and profiles for a specific technology, and it is extended to figure out correlations among variables through regression and Bayesian Networks analysis. In addition, specific socio-demographic data relevant to the needs and expectations were studied through the ANOVA test. This work belongs to the methodological framework of the IP4MaaS (Innovation Program 4 Mobility as a Service) project, which sets six demo sites on which this assessment method will be applied in a further stage. The concept of Effectiveness is applied in all the above-mentioned demo sites for the final assessment. Some IT innovations such as Location-Based Experience and Journey Planning have shown high Effectiveness. This work could be interesting for TSPs and IT (Information Technology) developers, researchers, policymakers, and organizations in the transport sector.