In a letter to the Rev. Mr Hakluyt, a well-known writer on sea-voyages and travels in the time of Elizabeth and James I, Dudley gives a curious account of his first voyage at the age of twenty-one. “... I weighed ancker from Southampton road the 6th of November 1594. Upon this day my selfe in the ‘Beare,’ a ship of 200 tunnes, as Admirall; and Captaine Munck in the ‘Beare’s Whelpe,’ Vice-Admirall; with two small pinnesses, called the ‘Frisking’ and the ‘Earwig,’ I passed through the Needles, and within two dayes after bare in with Plimmouth. But I was enforced to returne backe. Having parted company with my Vice-Admirall, I went wandering alone on my voyage, sailing along the coast of Spaine, within view of Cape Finisterre and Cape St Vincent, the north and south capes of Spaine. In which space, having many chases, I could meet with none but my countreymen or countrey’s friends. Leaving these Spanish shores, I directed my course, the 14th December, towards the Isles of the Canaries. Here I lingered twelve dayes for two reasons; the one, in hope to meete my Vice-Admirall; the other, to get some vessel to remove my pestered men into, who being 140 almost in a ship of 200 tunnes, there grew many sicke. I tooke two very fine caravels under the calmes of Tenerif and Palma, which both refreshed and amended my company, and made me a fleet of three sailes.... Thus cheered as a desolate traveller, with the company of my small and newe erected Fleete, I continued my purpose for the West Indies.