Automation in ports improves the safety and efficiency of port operations, allowing for more effective planning. Digital twin (DT) technology enables more effective use of autonomous technologies and supports the capacity for rapid assessment and instant decision-making. The integration of these two transformative technologies can create a more sustainable, efficient, and secure port ecosystem by automating port operations and enhancing them through simulations. A port's eligibility for maritime autonomous surface ships (MASS) depends on digital transformation and infrastructure obligations. The transformation of the ports and ships is expected to play an important role in port operations. This chapter addresses the potential and challenges of DT and autonomous technologies in the maritime industry and aims to provide a deeper understanding of their applications in this industry. The chapter provides valuable insights into the future efficiency, safety, and sustainability of ports and ships, two critical components in the maritime industry.