There, he worked as an engineer and shipbuilder, and designed and published Dell'Arcano del Mare (1645–1646), the first maritime atlas to cover the whole world.
In Italy, he styled himself "Earl of Warwick and Leicester", as well as "Duke of Northumberland", a title recognized by Emperor Ferdinand II.
[3] Dudley was given an excellent education and was enrolled at Christ Church, Oxford, in 1587, with the status of filius comitis ("Earl's son").
In turn, the 17-year-old Dudley married Margaret, a sister of Sir Thomas Cavendish, in whose last voyage he had probably invested.
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.
Dudley renamed them Intent and Regard, manned them with his sailors, and put Captain Woods in charge.
Then he sailed to Paracoa Bay for repairs and made a reconnaissance to San José de Oruña, but decided not to attack it.
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.
The Beare arrived at St Ives in Cornwall at the end of May 1595, and Dudley heard that Captain Woods 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.
[9] Dudley claimed to have been told in May 1603, by a shadowy adventurer called Thomas Drury, that his parents had been secretly married.
It was concluded that Sir Robert Dudley had been duped by Drury, who in his turn had sought "his own private gains".
Dudley married Elizabeth Southwell in Lyon in 1606, after they had received a papal dispensation because they were blood relatives, and they first settled in Florence.
Dudley designed and built warships for the arsenal of Livorno and became a naval advisor to Ferdinand I, Grand Duke of Tuscany, of the Medici family.
In 1608, Dudley convinced the Duke to send the privateer galleon Santa Lucia Buonaventura to Guiana and northern Brazil in the only tentative Italian colonization in the Americas, known as the Thornton expedition.
He continued contacts with the English court through Sir Thomas Chaloner, who was now a chamberlain to Henry Frederick, Prince of Wales.
He corresponded with the young Prince on the subjects of navigation and shipbuilding, and in 1611 tried to broker a marriage between him and Caterina, daughter of Duke Ferdinand.
Meanwhile, Henry Frederick had taken a fancy to Kenilworth Castle, calling it "the most noble and magnificent thing in the midland parts of this realm".
In addition to shipbuilding, Dudley was busy with many projects in Tuscany, including the Livorno's breakwater and harbour fortifications, draining local swamps, and building a palace in the heart of Florence.