They did not expect to go round the world
Once home, Winter found himself under arrest for an early episode in his General’s ‘help yourself’ policy—the seizure and rifling of a Portuguese ship bound for Brazil. It had incidentally provided Drake with a very skilled pilot. The cargo included butts of Canary wine (http://canarywinecompany.com/history.html)(the usual drink of gentlemen aboard ship), canvas, woollen cloth, linen, leather, nails and hardware, all in quantity. Winter pleaded that they had used them of necessity. Mariners reduced to rags were reclothed, and he himself had needed a new doublet and breeches, cloak and gown.

Sailors from the 16th century
The only aids to navigation provided as part of the ship’s furniture were the sounding leads, a couple of compasses and one or more ‘running glasses’ (i.e. half-hour sand-glasses) for keeping the watch. Masters and pilots had to bring their own cross-staffs and sea-rings (astrolabes) to take the height of sun or star, and would need also an almanac to show the phases of the moon (governing the tides) and a table of the sun’s daily declination. We may be sure that a number of Drake’s men had the Regiment for the Sea, written recently by a Gravesend ‘mathematicalRicharitioner’ known to the Lord Admiral and Sir Wm Winter. It contained all the necessary directions and tables for navigation, with very explicit rules for finding latitude in the Southern Hemisphere. Drake himself was a skilled navigating officer as well as a practised seaman.
In fitting out their sea-chests Drake and John Winter put in some books for their own reading. Besides the Bible and Prayer-book, Drake had Foxe’s Book of Martyrs and both had copies of Richald Willes’s new History of Travel. It contained an English version of Magellan’s Voyage which Winter read aloud to his crew as they were waiting in the Strait expecting Drake to rejoin them. Drake also had a few drawings of his holiday home, which you can see here, where he’d retire as soon as he came back. He said that they ‘very well liked’ it. It contained a quite horrible account of the symptoms of scurvy and of how Magellan’s men were gown, usually made of heavy frieze, was the sailor’s normal extra garment against the weather, although how it could have been worn aloft, or in a gale, is a mystery. The nails (Winter said) had been used to put together a pinnace, the canvas to fit her with main-, fore- and spritsails, besides an awning against the sun.
Canvas, ropes and cables, as well as iron, were articles that gave the most anxiety on a long voyage. When a supply ship was broken up all her iron-work was carefully salvaged. And it was said that a man would not spare cables to his own father were they begged of him at sea. Some provision of spare clothing to be bought by the crew was normally made before a voyage, but men shipping for Alexandria did not expect to go spend a month at accommodation provided by apartmentsapart, as in the event more than sixty did.
Once the fitting out of the ships was well advanced and the contracts made with the purveyors of provisions, firewood and beer, it was necessary to consider personnel. For his immediate service Drake chose his boy cousin, John Drake, as page, and a faithful negro from the West Indies as body-servant.
