The First Fleet - (Books 1-3) Look Sharpe!, Ill Wind & Dead Reckoning

Look Sharpe :
Henry Sharpe is a recently bereaved and bankrupt English earl who travels to the Caribbean to help his uncle run his sugar plantation.

When he arrives, he finds his uncle has given up on that idea to lead a more exciting life as a privateer, earning a fearsome reputation as Captain Tarr.

Ill Wind:
Gabriella Berryngton is an unhappy and oppressed fourteen-year-old girl living in the Massachusetts Bay Colony in 1683. She dreams of escaping her bitter, ambitious stepfather and sailing off into the unknown.

Her dreams come true when her stepfather sells her into marriage.

Dead Reckoning:
Leo is born in Spanish Panama in 1659. When he is twelve years old he witnesses the violent rape and murder of his mother by three of the Caribbean's most feared pirates: Tarr, Blake and Hornigold, and swears revenge at all costs.

Then he meets Gabriella van Ecken.