Dynamic packaging has been introduced as an innovative technology allowing for the automated online configuration and assembling of packaged travel products for individual customers. While dynamic packaging has been widely accepted by customers in UK and US markets, the possible strategic impacts enabled by dynamic packaging technologies are still uncertain. This article provides a study of the strategic opportunities enabled by dynamic packaging, highlighting the key success factors. Current dynamic packaging applications of the three major online travel agencies are evaluated on the basis of the developed analysis framework. The results show that an appropriate level of integration of tourism information systems is a key factor for further realizing the strategic opportunities of dynamic packaging. We then discuss Web services and semantics as a possible solution for overcoming the interoperability problems that (current) dynamic packaging applications face.