Vacation planning is a frequent laborious task which requires skilled interaction with a multitude of resources. This paper develops an end-to-end approach for constructing intra-city travel itineraries automatically by tapping a latent source reflecting geo-temporal breadcrumbs left by millions of tourists. In particular, the popular rich media sharing site, Flickr, allows photos to be stamped by the date and time of when they were taken, and be mapped to Points Of Interest (POIs) by latitude-longitude information as well as semantic metadata (e.g., tags) that describe them.Our extensive user study on a "crowd-sourcing" marketplace (Amazon Mechanical Turk), indicates that high quality itineraries can be automatically constructed from Flickr data, when compared against popular professionally generated bus tours.