For more than 145 years, Jamaica was under Spanish control. Claimed by Christopher Columbus in 1494 and settled in the early 1500s, the island remained a quiet colonial outpost in the Spanish West Indies. Unlike the bustling trade hubs of Havana or Cartagena, Jamaica was sparsely populated and largely neglected. Most of its economy relied on cattle, subsistence farming, and a small enslaved African population. That all changed in May 1655, when England launched a bold and ultimately successful invasion.
The Western Design and a Failed Beginning
The invasion of Jamaica was not part of the original plan. In 1654, Oliver Cromwell launched what he called the “Western Design” — a grand plan to expand English influence in the Caribbean and weaken Spain’s hold on the region. Command of the mission was shared between General Robert Venables and Admiral William Penn. Together, they led a force of around 7,000 men aboard 38 ships. The goal was to strike at major Spanish possessions, but poor planning would soon doom their initial effort.
Their first target was Hispaniola, one of Spain’s wealthiest islands. The English landed in April 1655 but were ambushed, outmanoeuvred and overwhelmed. Torrential rains ruined supplies and gunpowder, and troops suffered massive losses. With morale shattered and nearly a third of their men dead, Venables and Penn abandoned the assault. To avoid returning home empty-handed, they turned to Jamaica — seen as an easier prize with fewer defences.
May 19, 1655 – The British Invasion Begins
On 19 May 1655, the English fleet anchored off the coast of Jamaica near Point Morant. Spanish officials, already warned of the fleet’s approach, scrambled to prepare. The island’s defences, however, were minimal and no match for the large English force.
May 21 – Landing at Caguaya Bay
Two days later, on 21 May, the English sailed into Caguaya Bay, now known as Kingston Harbour. Because of the shallow waters, Admiral Penn transferred to a lighter vessel to direct the landing. English troops came ashore with little resistance and quickly began to move inland toward the capital, Santiago de la Vega.
May 23–25 – Push to the Capital
The Spanish, outnumbered and under-supplied, began to retreat. Some fled for the mountains, while others prepared to evacuate the island altogether. During the chaos, Spanish settlers freed their enslaved Africans, many of whom also escaped inland. These individuals and their descendants would later become known as the Maroons — key figures in Jamaica’s long history of resistance.
By 25 May, the English had occupied Santiago de la Vega. What little resistance remained was scattered. The English suffered minimal casualties and quickly established control over the town.
May 27 – Spanish Surrender
On 27 May 1655, Spanish Governor Juan Ramírez de Arellano formally surrendered. The terms allowed Spanish inhabitants two weeks to leave the island peacefully. Many departed for Cuba, including the governor himself, who later died en route to Mexico. The English had claimed Jamaica, but the victory came with a steep price and uncertain future.
The swift capture of Jamaica had immediate military value for England, but it also marked the beginning of a much longer struggle to hold the island. Though the Spanish no longer held formal power, their former slaves, now free, took to the hills and launched a campaign of guerrilla resistance in alliance with Spanish holdouts. The English, still weakened by the failed Hispaniola campaign, would soon realise that keeping Jamaica was far more difficult than taking it.
Aftermath and Fallout
While the English had achieved a tactical victory within a week, the invasion did not bring the quick spoils or glory Cromwell had hoped for. The situation on the ground remained unstable. Disease swept through the English camp. Supplies were low, and morale was poor.
Venables, already weakened by illness, was left behind when Admiral Penn sailed for England with half the fleet on 25 June. Desperate to tell his side of the story, Venables followed weeks later. Both men were imprisoned in the Tower of London upon their return for abandoning their posts without permission.
Still, the events between 19 and 27 May 1655 marked a turning point not just in Jamaica’s colonial history but in the Caribbean’s wider geopolitical landscape.
In the hills of Jamaica, the seeds of resistance were already taking root, setting the stage for the fierce guerrilla warfare that would follow. The invasion was over. The real battle for Jamaica was just beginning.
Next: Part 2 – Guerrilla War in the Hills
We’ll explore how Jamaica’s newly freed Maroons teamed up with Spanish forces to resist the British occupation.
