Lear had considered visiting the Holy Land in 1849 and again at the beginning of 1854, but it was only in 1858 that he undertook a three month tour, spurred by a commission from his friend and patron Lady Waldegrave to paint her a view of Jerusalem (Christie's, 29 July 1977, lot 174) and another subject. Accompanied by his manservant Georgio Kokali, he arrived in Jerusalem on 28 March and, in spite of the crowds of Easter pilgrims, found it 'far more beautiful than [he] had expected'. On 2 April he left Jerusalem and travelled south to Bethlehem and Hebron, where he picked up an escort of 15 men for the dangerous desert journey to Petra. They returned to Jerusalem via the Dead Sea and Masada, then went north to Jericho. Having failed to see Nazareth and Galilee, he returned yet again to Jerusalem and, after resting there for a few days, decided to go on the Lebanon, arriving there on 11 May. He was thrilled by the famous cedars, so ancient and vast in scale, and he was struck by the beauty of Damascus. As he wrote from the city on 27 May in a long letter to Lady Waldegrave: 'Imagine 16 worlds full of gardens rolled out flat, with a river & a glittering city in the middle - & you have a sort of idea of what the Damascus pianura is like.' (V.Noakes, Edward Lear, Glasgow, 1968, p.159). It was to be the last site to engage his attention on the journey. The hottest season of the year had now begun, and he had suddenly had enough. Two days later he left Damascus to return to Corfu, where his friend Franklin Lushington was based in the legal service.
One of Lear's 'tyrants' which he painted as a group for his summer exhibitions during the 1860s. Lear presumably mis-remembered the year of his trip to the Holy Land when completing this watercolour in 1864.