In 1655 Oliver Cromwell, England's Lord Protector, sent a fleet to attack and seize Spanish possessions in South America. The English was flexing its muscles on the international stage and for political, religious and commercial reasons chose to attacked a weakened Spain in the West Indies believing it a soft target. In late 1654 possibly the largest military force to date ever to leave English shores set sail from Portsmouth under the command of General Robert Venables and Admiral William Penn. This book describes the reasons for war with Spain, the army and fleet assembled at Cromwell's bidding and its objective. The attack on Hispaniola in April 1655 will be explained in detail along with the reasons for its failure as will the occupation of Jamaica as will the beginnings of the Spanish war of resistance. A subsequent volume will recount the war on Jamaica from the end of 1655 until 1660. This work draws upon extensive primary source material from England and Spain as well as the copious amounts of letters and narratives of soldiers and sailors present, from both sides.