Stringent regulations regarding environmental protection and energy efficiency (i.e., emission limits regarding NOx, SOx pollutants and the IMO greenhouse gases reduction target) will mark a significant shift to the maritime industry. In the first place, the shipping industry has strived to work towards feasible technologies for regulatory compliance. Nevertheless, life cycle cost appraisal attaches much consideration of decision-makers when it comes to investment decisions on new technologies. Therefore, the life cycle cost analysis (LCCA) is proposed in this study to evaluate the cash flow budgeting and cost performance of the proposed technologies over their life cycles. In the second place, environmental regulations may support innovation especially in the era of digitalization. The industrial digitalization is expected to revolutionize all of the aspects of shipping and enable the achievement of energy-efficient and environmental-friendly maritime operations. The so-called Internet of things (IoT) with the utilization of sensor technologies as well as data acquisition systems can facilitate the respective maritime operations by means of vessel operational performance monitoring. The big data sets obtained from IoT should be properly analyzed with the help of Artificial Intelligence (AI) and Machine Learning (ML) approaches. Our contribution in this paper is to propose a decision support framework, which comprises the LCCA analysis and advanced data analytics for ship performance monitoring, will play a pivotal role for decision-making processes towards cost-effective and energy-efficient shipping.