Background: Port digital transition is central to competitiveness and sustainability, yet existing frameworks devoted to such transition toward smart port are descriptive, technology-centered, or weak on data governance. This study designs and empirically refines a comprehensive and novel ten-step roadmap relative to existing Port/Industry 4.0 models, synthesized from 14 partial frameworks that each cover only subsets of the transition, by considering data governance and consolidating cost, time, and impact in the selection step. Methods: We synthesized recent Industry 4.0 and smart port-related frameworks into a normalized sequence of steps embedded in the so-called roadmap, then examined it in an exploratory case of a technology deployment project in a Canadian port using stakeholder interviews and project documents. Evidence was coded with a step-aligned scheme, and stakeholder feedback and implementation observations assessed whether each step’s outcomes were met. Results: The sequence proved useful yet revealed four recurrent hurdles: limited maturity assessment, uneven stakeholder engagement, ad hoc technology selection and integration, and under-specified data governance. The refined roadmap adds a diagnostic maturity step with target-state setting and gap analysis, a criteria-based selection worksheet, staged deployment with checkpoints, and compact indicators of transformation performance, such as reduced logistics delays, improved energy efficiency, and technology adoption. Conclusions: The work couples theory-grounded synthesis with empirical validation and provides decision support to both ports and public authorities to prioritize investments, align stakeholders, propose successful policies and digitalization supporting programs, and monitor outcomes, while specifying reusable steps and indicators for multi-port testing and standardized metrics.