[1] In 1868, he replaced Andrew Tucker Squarey as secretary of the Liverpool Steamship Owners' Association, a position he held for 40 years.
[3] He was also the secretary of the North Atlantic Steam Traffic Conference, another grouping of shipowners, and sought to defend the British merchant navy from international marine courts being established that were under US influence.
[5] A Unionist associate, in strongly Home Ruler Liverpool, was James Willcox Alsop (1846–1921), another leading solicitor.
[1][12] From the mid-1880s, his art collection was housed there: it was reviewed in The Athenaeum in 1886, which noted works by Thomas Gainsborough, Joshua Reynolds and George Romney.
[1] A patron of the arts, Hill supported Edward Robert Hughes, and bought works of Liverpool artists including the marine painter William Joseph Julius Caesar Bond.
He later built a house on it, for his painter wife Caroline, at a location on the Jerusalem–'Anata road: it was described in handbooks as "Mr Gray-Hill's villa".
[21] Bentwich visited the Gray-Hills at their house in 1914, hearing Sir John's concerns about town planning and slums in Jerusalem.
[19] The purchase of land on Mount Scopus was piecemeal and used funds from Isaac Leib Goldberg, and was carried out by Arthur Ruppin on behalf of the World Zionist Organization.
Details were agreed with the Hill family in 1914, before World War I intervened, but the sale took effect in 1918,[8][19][23][24] January 31 for the paid sum of £6,500.
[35] An earlier journey to Petra, in 1890, had resulted in Hill and his wife being detained for ten days by Arabs asking for payment.
[37] The Bedouin considered that more casual tourism in the area, which was being supported by the central government and plans for the Hejaz railway, threatened a traditional pattern of camel hire and pilgrim travel.
[38] In 1903 Caroline Gray Hill published in The Windsor Magazine an article "A Journey by the Way of the Philistines", about a route starting in El Qantara, Egypt and passing through Arish and what is now the Gaza Strip, to Bethlehem.