The advancements of technology have been making digital cameras more and more affordable for everyone. Consequently, digital photographs have grown exponentially this last decade and have been making it beyond the abilities of people to easily manage their own photo collections. Annotation is one of the solutions to solve this burden. Therefore, we propose a semi-automatic annotation engine with contextual metadata generation. Photos with geo-referential information such as Global Positioning System (GPS) are the current tendency, Using the exact location information given by GPS, together with times-tamps, our novel engine semi-automatically generates contextual metadata for each photo from different sources of information namely the public news and users' personal information. We have designed, implemented and tested our system.