Jenkinson started on his eastern travels from Moscow in late April, 1558, well furnished with letters from the emperor, directed to all kings and princes through whose dominions he might pass, soliciting safe conduct for him. He was accompanied by two others of the Muscovy Company’s men—Richard and Robert Johnson—and a Tartar guide. His ultimate aim was a passage to “Cathay” from Russia by way of the Caspian Sea, and “Boghar” (Bokhara) overland. He sailed from Moscow on the Moskva River in a small but staunch vessel and carried along with him “divers parcels of wares” for barter and trade as he travelled. At Nijni-Novgorod, at the junction of the Oka and the great Volga rivers, he joined the train of a captain, or governor, who had been sent out by the emperor to rule at Astrakhan, and who had under his command “500 great boates,” some laden with soldiers and army supplies, others with merchandise. Astrakhan was reached in the middle of July. Thence, in early August, Jenkinson and his comrades proceeded alone, and entered the Caspian Sea, the first of Englishmen to plow its waters. Here as they sailed they displayed in their flags the “redde crosse of S. George” for “honour of the Christians.” After weeks of coasting along the shores, and much difficult navigation, they landed, early in September, “overthwart Manguslave”—Mangishlak, in long after times known as Fort Novo-Alexandrovsk. Here they joined a caravan of a “thousand camels” and entered upon a long overland journey, full of adventure and not without peril, by way of Khiva to Bokhara. For twenty days they travelled in a “wilderness from the seaside without seeing town or habitation.” At one time they were driven by necessity to eat one of their camels and a horse. During the twenty days they found no water but such as they drew out of “old deep wells which was very brackish and salt.” Far along on their way they encountered bands of “rovers” (highwaymen), one of forty men under a banished prince, and had some sharp fighting. Bokhara was at length reached two days before Christmas. Presenting the emperor’s letters to the ruler here, Jenkinson was favourably received. Soldiers were sent out after the banished prince’s rovers, and four being captured they were hanged at the palace gate “because they were gentlemen.” Jenkinson remained in the city for more than two months, keenly observant of men and things. He saw merchants and caravans from various countries, Persia, India, and others, and heard much about routes to “Cathay.” He would have pressed on to Persia, but was prevented by wars.