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 All through the month of January, 1600, the expedition was being fitted out in the Thames. Each ship was provided with twelve streamers, two flags, and an ensign. Stores and provisions of all kinds were stowed in the holds, as well as merchandise; and merchants were appointed to each ship to superintend the trading operations. The queen prepared letters to the princes of India, including one to the Sultan of Acheen; and suitable presents accompanied them. Mr. Richard Hakluyt compiled much useful information respecting the commodities of the different countries, instructions "touching the preparing of the voyage," and several maps. The officers and others received "bills of adventure" on the gains of the voyage — that is to say, each was to receive a reward on a fixed scale with reference to the yield of the return cargo.

The fleet sailed from Woolwich on the 13th of February, 1600, but it was long delayed in the Downs by calms, and the ships had to put into Dartmouth to complete their stores; so that it was the 2nd of April before they finally sailed for the Canaries. The usual fatal sickness broke out while the fleet was detained by equatorial calms. Captain Lancaster, however, captured a Portuguese ship and got out of her 146 casks of wine, 176 casks of olive oil, and a quantity of meal, which proved a great addition to the supply of provisions. The victualler Guest was emptied and turned adrift. The expedition crossed the line on the last day of June.

The ravages of scurvy continued, so that when Table Bay was reached on the 9th of September, Captain Lancaster had first to anchor his own ship, and then to send his boats away, with working parties, to perform the same office for his consorts, whose crews were too weak to bring their ships to. The Dragon's working parties also hoisted out the boats for the rest of the fleet. The reason why the men in Lancaster's ship were so much healthier than the others was that he took the precaution of providing a supply of lemon-juice. He gave three spoonfuls to each man every morning fasting, by which means he cured many of his sailors and kept the rest from scurvy. The sick were landed and put under canvas on shore. Very good arrangements were made for the traffic with natives, cattle and sheep were purchased, and the sick soon began to gain strength on a diet of fresh meat and vegetables. But the terrible disease had carried off one hundred and five men before any effective remedy could be applied.