Abstract During the last decades, the World Wide Web has rapidly grown in size and complexity. A huge amount of complex Web Applications is available to support the fulfilment of the most diverse tasks, by providing large amounts of information and functionality. However, the high diversity of Web users makes difficult to identify and provide an easy access to data and services that best fit their individual interaction goals. Adaptive Web Applications is a type of Web-based systems that faces this problem, by automatically adapting the access to information pieces, services and hyperlinks to the characteristics of users and their interaction context. The development of these systems demands the adoption of an engineering approach that facilitates the specification of the required adaptive features and the user characteristics on which the adaptation is based. The present thesis introduces a Model-Driven approach to the development of Adaptive Web Applications. This proposal integrates traditional development practices of Web Engineering with proved concepts from the Adaptive Hypermedia community. Taking as a basis the OOWS (Object Oriented Web Solutions) development process of Web Applications, this proposal defines a set of conceptual primitives (called Adaptive Primitives) that allow expressing well-known adaptive techniques at a high abstraction level. The definition of these primitives is supported by a User Modelling proposal. Furthermore, a set of modelling strategies offers multiple alternatives to incorporate Adaptive Methods in OOWS navigational schemas, based on the introduced Adaptive Primitives. In order to support the modelling of adaptive features, a Requirements Model is defined, allowing the specification of Adaptivity Requirements, along with the information requirements related to the application users. Finally, a set of transformation rules is introduced, with the goal of facilitating the traceability of these requirements to the conceptual modelling phase.