Thomas Cook, innovator of the conducted tour, organized his first one-day rail trip in 1841 and in 1860s, with his son, John Mason Cook, created Thomas Cook & Son brand by opening office in London to sell tickets for domestic and international travel. Thomas Cook escorted his first party to Egypt and Palestine in 1869. By the end of the nineteenth century, the company had arranged travel to Palestine for about 12,000 people. One of these travellers was German Emperor Kaiser Wilhelm II. Making travel arrangements of Kaiser in 1898 crowned the efforts of the company. This study provides the first examination of the archive documents on business agreement and correspondences between Thomas Cook & Son and the Ottoman Court for Kaiser's journey to the Holy Land. This study also aims to provide insight into how their entrepreneurial spirit contributed to the contemporary patterns of tourism management.