Expeditions
In 1594, Dudley assembled a fleet of ships, including his flagship, the galleon Beare, as well as the Beare's Whelpe, and the pinnaces Earwig and Frisking. He intended to use them to harass the Spaniards in the Atlantic. The Queen did not approve of his plans, because of his inexperience and the value of the ships. She did commission him as a general but insisted that he sail to Guiana, instead.
Dudley recruited 275 veteran sailors, including the navigator Abraham Kendal, and the captains Thomas Jobson and Benjamin Wood. Dudley's fleet sailed on 6 November 1594, but a sudden storm separated the ships and drove the vessels back to different ports. Dudley sent word to the captain of the Beare's Whelp to join him in the Canary Islands or Cabo Blanco, and he sailed again.
At first, Dudley's trip proved unlucky: the Earwig sank, and most of the vessels he encountered were friendly. Dudley led only one raid in the Gulf of Lagos.
In December, the expedition finally managed to capture two Spanish ships at Tenerife. Dudley renamed them Intent and Regard, manned them with his sailors, and put Captain Wood in charge. He sailed to Cabo Blanco, expecting to meet the Beare's Whelpe there, but it did not show up. Dudley's fleet sailed to Trinidad and anchored at Cedros Bay on 31 January 1595. There, he discovered an island that he claimed for the English crown and named Dudleiana. Then he sailed to Paracoa Bay for repairs and made a reconnaissance to San José de Oruña, but decided not to attack it.
Dudley divided his forces, sending the Intent and Regard to the north. In Trinidad, he recruited a Spanish-speaking Indian who promised to escort an expedition to a gold mine up the Orinoco River. The expedition, led by Captain Jobson, returned after two weeks; as it turned out, their guide had deserted them, and they had struggled back. Dudley returned to Trinidad.
On 12 March, Dudley's fleet sailed north, where it finally captured a Spanish merchantman. It then sailed on to Cabo Rojo, in Puerto Rico, waited for suitable prey for some time, and then sailed towards Bermuda. A storm blew the Beare north to near what is now New England before the fleet finally reached the Azores. Low on provisions and working guns, Dudley sailed for home, but he met a Spanish man-of-war on the way. He managed to outmanoeuvre and cripple it in a two-day battle, but decided not to board it. The Beare arrived at St Ives in Cornwall at the end of May 1595, and Dudley heard that Captain Wood had taken three ships.
The next year, 1596, Dudley joined Robert Devereux, 2nd Earl of Essex, to serve as commander of the Nonpareil in an expedition against Cádiz. He was later knighted for his conduct in the Capture of Cádiz, although what he did is not recorded. Shortly afterwards he married Alice, daughter of Sir Thomas Leigh of Stoneleigh.
In 1597, Dudley sent Captain Wood on a trading voyage to China with the Beare, the Beare's Whelp and the Benjamin, but they never returned.
