World literature teems with the portrayal of famous cities throughout the world. This kind of literature is unanimously known as city literature. It does not merely describe and portray places, objects, and landscapes for their own sake, it, however, gives readers a revisionist perspective to look afresh and introspectively into self, history, and culture. This paper aims to shed light on a city that witnessed great changes throughout its history. It is called Sana’a, the capital of Yemen, and it is one of such world-famous and ancient cities about which interesting and rich literature has been written. Sana’a has been immortalized in the prose and poetry of local and international prolific and intelligent writers such as Abdu al-Aziz al-Makkali, a famous contemporary Yemeni poet. Sana’a is magnificently portrayed in different exotic images in al-Makkali’s collection of poetry entitled Book of Sana’a. The poet engages in a kind of dialogue with the city in a personal experience and unique particularity, but in the process, this particularity becomes cosmopolitan. Each poem is located in a particular space which gives the poet and reader alike a sense of the place, history, and culture, and an intense feeling of wider identification and empathy. Sana’a is anthropomorphically portrayed as a beautiful woman, sad woman, beloved lady, spirit, and city of heaven. It is fantastically depicted as a unique piece of artifact molded and designed by the hands of God. So, this piece of research attempts to analyze social and political imports and the different images of the city employed by al-Makkali in his poetic work: Book of Sana’a. As a theoretical framework, the paper adopts both historical theory of criticism as well as the formalist theory, so the analysis is focused on both context and text of the selected poems.