The Maldives is a Small Island Developing State which depends on sea-borne transport connectivity for trade and inclusive nationwide growth. The high international freight costs to its small domestic market are aggravated by deficiencies in services and capacity in the Port of Male', the sole maritime gateway to the country. Male' City is the main hub for the distribution of goods for the whole country. It is densely populated, hence the movement and storage of goods within the city has exacerbated congestion. The gateway and distribution function of Male' port introduces bottlenecks and constraints to efficient transport and logistics in the Maldives. Moreover, due to the prevailing institutional arrangements, Maldivian ports have developed in an ad-hoc manner over the years. It is anticipated that the ports will not be able to accommodate future demand if current conditions are left to continue. This paper aims to develop an adaptive port master plan over the time horizon of 20 years, to address the above-mentioned issues. The tools for adaptive port planning were used to address uncertainties and vulnerabilities in the development of the masterplan. The basic plans encompass the development of Male' Commercial Harbour as an efficient gateway and distributor. A distribution network was designed to connect Male' with the regional ports. The actions to increase robustness and flexibility were translated into projects with no flexibility (ad-hoc), just-in-time flexibility and just-in-case flexibility. In summary, the 20-year vision for Maldivian ports is to become an international gateway port with an efficient ship to shore operation with fast and efficient domestic distribution via a roll-on/roll-off network connecting the far reaches of the country.