This study addresses an important issue that has occupied the minds of Muslim men and women, both in the past and present, namely the question of requiring a mahram for a woman's travel. The current study deals with this issue through an examination of the sayings of the Prophet Muhammad—peace be upon him—and the statements of ancient scholars, as well as the opinions of contemporary scholars, in a detailed and analytical jurisprudential study. The study aimed to delve into and scrutinize the prophetic hadiths and the statements of scholars, reverting to their texts to understand the rationale behind the ruling, to arrive at a Sharia ruling that aligns with the prophetic hadiths, the rationale, and the benefit upon which the ruling is based, and to connect it with the contemporary context. The study concluded that scholars have differed on this issue both in ancient and modern times. Some adhered strictly to the apparent meanings of the mentioned hadiths, thereby prohibiting women's travel without a mahram, without any exceptions. Others have made exceptions for certain cases, such as an elderly woman who is not desired and a woman travelling with a group of trustworthy women, as well as the safety of the journey, and that this applies to every person travelling with the intention of obeying Allah, whether obligatory or non-obligatory, such as visiting and trading.