Destination familiarity has been analyzed for many years as an important factor influencing the perceived attractiveness of a destination and its image. However, previous research has concentrated on this relation considering familiarity with a destination as a whole, while the issue of familiarity with particular elements of a destination has not been explored. The current research aimed to detect if and how familiarity with three selected elements of a destination, namely, tangible tourism attractions, events, and traditional cuisine and dishes, impacts the perceived attractiveness of a city destination. The research was conducted using the following four Polish cities as examples: Gdańsk, Katowice, Łódź, and Wrocław. The research questionnaire was distributed among the citizens of another Polish city—Krakow. Over 200 responses were received. The results show that familiarity with tangible attraction was correlated with high perceived attractiveness of a destination, while the other two factors did not impact the level of perceived attractiveness. The results were achieved on the basis of the indication of several scientific and practical conclusions.