An essential difference between the western and eastern provinces of the Roman Empire is the fact that sophisticated urban cultures had developed in Asia Minor and the Levant centuries before the Romans arrived. Underlying the Hellenized, and later Roman, veneer was a myriad of older local traditions and languages, which had an immense impact upon Roman religious tradition through elements such as the introduction of new religious practices. Following the path of previous studies, in this article we try to discern how Roman culture was inherited and adapted to the heterogeneous Eastern traditions and how it could be reflected in the architecture and urban layout, mainly in what concerns to the orientation of the urban structures. Considering ancient writings, such as those of Higynius Gromaticus (Constitutio, I), the orientation of these features could follow the position of certain celestial bodies, mainly the sun, which would imply a careful observation of the sky. Developing the lines of previous studies on the orientation of Roman settlements in the western part of the Empire (González-García et al., 2014 & Rodríguez-Antón et al., 2016), a number of Roman cities and military settlements in modern-day Jordan, Syria and Palestine are analysed here. Through this approach, we try to obtain a first insight into whether their orientations looked towards astronomical positions and wether there existed common patterns comparing with those sites previously measured in Hispania or Britannia. This would help us to obtain a wider vision of Roman ritual practices, cosmovisions and how Roman culture could have evolved, spread and became assimilated through lands and time.