In 1590, Christopher Newport in a partnership with famed London Merchant John Watts had participated in the highly successful expedition to the Caribbean.

[5] Back in England during the winter of 1591/1592, Newport prepared for another expedition to the Caribbean as a joint stock operation, this time against the island of Hispaniola.

The English Crown granted letters of reprisal to Newport for an expedition comprising four ships totalling some 300-350 tons with nineteen cannon and 200 men in all.

[7] On April 4, 1592, they arrived off the island of Hispaniola, and after landing on a deserted beach, moved inland and replenished with food and water.

On 2 April Newport transferred 110 men from his ships to make a surprise attack on the Spanish town of La Yaguana.

Just as the English come into the town, 150 Spanish militia including a detachment of cavalry then launched an attack with help of 200 stampeding cattle.

[15] He thus by one day's inroad destroyed the hard earnings of many years industry and threw a blight upon the prosperity of the colony which, according to Jonathan Brown in 1837, no future effort could overcome.

[16] Newport after finishing with Hispaniola sailed to the Bay of Honduras looking to wreak havoc on the Spanish settlements of Truxillo and Puerto de Caballos.

[17] Sailing onto Puerto de Caballos the English went ashore and seized the town without opposition - its inhabitants had fled inland.

They landed on one of the islands and encountered the Calusa natives who were friendly - willing to trade precious metals for tools, water and food.

Just before they got to the islands in August, they encountered Roebuck Captained by John Burgh, who informed of them that he was part of the fleet (led by Martin Frobisher) outfitted by the Queen which was attempting to surprise Portuguese vessels returning from the East Indies heading to the area.

[19] In this Newport assisted in the capture of the rich Portuguese carrack Madre de Deus after a long naval battle off the island of Flores.

[24] The actions of Newport on the coast of Northern Hispaniola forced the Spanish Governor Portocarrero to order the evacuation of the towns there – Bayaba, Puerto Plata and La Yaguana were moved further South.