The cruise industry is a highly concentrated business in terms of players and markets. Vessel deployment strategies and itinerary design by cruise operators are primordial and are affected by market and operational considerations. This paper focuses on capacity deployment and itineraries in two major cruise markets: the Caribbean and the Mediterranean. We argue that the cruise industry sells itineraries, not destinations, implying a level of flexibility in the selection of ports of call, but still bound to important operational considerations. The paper also reveals that the two cruise markets are not functioning independently but are interconnected in an operational manner, particularly through the repositioning of vessel units to cope with variations in seasonal demand among the regional markets.