Abstract-Contemporary travel information services are connected to huge amount of travel related data used for improving personalized suggestions. Such suggestions include finding better routes, access to amusement and educational amenities implemented as digital services, as well as the features for people collaboration, and for planning leisure time with respect to existing attractiveness evaluation algorithms under time-budget constraints. Much effort is required for supporting personalized itineraries construction in such a way which would leverage existing cultural and technological user experience. In this paper we analyze the underlying algorithms and major components being an implementation of the proposed model investigated with particular attention to annotated leisure walk route construction, traveler collaboration and travel meeting management. In sum, we make an effort to address a number of complex issues in the area of developing models, interfaces and algorithms required by modern travel services considered as an essential application of a human-centric computing multidisciplinary paradigm.