The document assesses of the situation of the maritime sector in CARICOM and presents a series of new observations and issues. Challenges and barriers in the maritime sector, or problems created through inefficiencies in the maritime sector are analyzed for: maritime freight transport, cruise shipping, ports and yachting. Whilst the first three are part of the original structure of the study, the fourth is included to show the full extension of the maritime sector. To be able to understand the challenges and role of maritime transport in a regional and global context, it is essential to consider the physical geography of the CARICOM region; CARICOM is a "conglomerate" of states that have comparable historical development paths of colonial dependency. The countries are spread out throughout the Caribbean basin and do not form a continuous territory. While cooperation between this diverse group of countries has historically developed slowly, the ambitious goal to create a Caribbean Single Market Economy (CSME) and the enlargement of CARICOm's membership has accelerated the speed of integration. Common strategies for the CARICOM maritime transport sector are always challenged by regional competitors from outside the CARICOM group. As the CARICOM region is geographically discontinuous, this fact contributes to difficulties in setting up joint strategies and regulatory frameworks, because these might easily be obstructed by the competitors. A number of CARICOM countries (esp. Jamaica and The Bahamas) benefit from their intermediacy setting in the principal East-West global trade routes, which pass through the Panama Canal on the one hand and for North-South routes between South America and North America on the other hand. A number of ports have been able to take advantage of their geographical position, because of the ascendant hub and spoke network in global liner shipping. On the contrary the scale of hinterlands and slow port reforms has been a drawback for development of other ports.The transshipment market carries a significant risk for ports, since shipping lines tend to act footloose in the cost and scale driven container shipping market. The transshipment ports in CARICOM have based their success on different strategies. Freeport uses its unique geographical position and the artificially created barrier to Short Sea Shipping (SSS) in the US by the Jones Act. Kingston has adopted a strategy to tie shipping companies to the port, by developing dedicated terminals and attracting private investment from shipping companies.Research on freight rates in the Caribbean is of high interest, as it depicts key influencing factors. The empirical analysis discusses how factors like distance between origin and destination of cargo flows, port infrastructure, connectivity, and the number of services among others influence freight rates.Further, CARICOM countries are part of the most attractive region for cruise ship tourism. However, CARICOM countries suffer from the footloose behaviour of the oligopolistic cruise line industry and the related bargaining power of these lines. Yachting activities have been developing at a high speed and bring new challenges and opportunities for development.