Sir Francis Drake: His Voyage, 1595: Together with the Spanish account of Drake's attack on Puerto Rico

In Short

This volume presents two eyewitness accounts of Sir Francis Drake’s disastrous 1595 expedition to the West Indies. Thomas Maynarde, an officer on board, details the bickering between Drake and Sir John Hawkins, their failed attacks on Spanish strongholds, the disease that ravaged their crews, and Drake’s ultimate death at sea. A complementary Spanish report describes the defense of Puerto Rico from the garrison's perspective. It endures as a vivid, unvarnished correction to the heroic myth of Elizabethan privateering, exposing the greed, poor planning, and tactical failures that doomed the enterprise.

The Story

The campaign opens in August 1595 as twenty-seven ships carrying two thousand five hundred men depart Plymouth under the joint command of Sir Francis Drake and Sir John Hawkins. Almost immediately, internal friction divides the force. Because each commander victualled half the fleet, they treat their respective squadrons as private commands. Early council meetings descend into heated arguments when Drake admits to over-crowding his own ships and demands that Hawkins absorb three hundred men. Hawkins refuses to accept them unless formally begged, a humiliation Drake’s pride cannot bear. Further operational security is shattered when Hawkins openly announces their secret targets—Puerto Rico, Nombre de Dios, and Panama—in full hearing of the ordinary sailors.

Disaster follows swift upon poor coordination. After a failed landing in the Canaries, the fleet reaches the Virgin Islands, where Hawkins falls gravely ill and dies just as they anchor off Puerto Rico. The Spanish garrison, forewarned and heavily fortified with seventy cannon, repulses the English assault. A Spanish shot strikes the flagship Defiance during dinner, killing several senior officers, while a night attack on five Spanish frigates costs the English over four hundred men and multiple boats for the destruction of a single enemy vessel.

Driven off from Puerto Rico, Drake turns toward the Spanish Main. His forces land at Rio de la Hacha and Nombre de Dios, but they find the settlements stripped bare. The inhabitants have removed their gold and silver to hidden mountain strongholds or fortified positions further inland. A land force sent over the mountains toward Panama is repulsed by Spanish troops, forcing a retreat back to the coast.

Sickness sweeps the crowded, ill-provisioned ships. Driven by stubbornness and despair, Drake anchors near the barren island of Escudo de Veraguas, a notoriously unhealthy swamp where food runs short and men die daily. Confessing privately to Maynarde that he no longer recognizes the West Indies, Drake clings to the belief that fortune will yet make them rich. Instead, he contracts dysentery and dies at sea in January 1596. Command passes to Sir Thomas Baskerville, who fights off Spanish warships and gathers what remains of the shattered fleet to steer a desperate, hungry course back to England.

How It Unfolds

The fleet sets sail Twenty-seven vessels leave Plymouth under divided command, immediately plagued by squabbling over troop distribution and victuals. Hawkins publicly blabbers their secret destinations, destroying any chance of surprise.

Disaster at Puerto Rico Hawkins dies as the ships anchor off San Juan, where entrenched Spanish batteries turn back the fleet. A single cannon shot rips through Drake's mess room, killing senior officers, and a bloody night attack on Spanish frigates fails to break the harbor's defenses.

Empty towns and scorched earth Mariners march on Rio de la Hacha and Nombre de Dios, only to find the gold already moved inland. An attempt to force a march over the mountains to Panama fails against Spanish ambushes and harsh terrain.

Fever on the coast Stranded off waste islands with dwindling provisions, the crew succumbs to tropical disease. A humbled Drake admits to his officers that his luck has run out, soon falling ill himself and dying at sea.

The retreat home Under Sir Thomas Baskerville, the surviving ships battle enemy warships, dodge shoals, and scavenge for dried beef in Jamaica before dragging their under-manned, battered vessels back to England.

The People

• Sir Francis Drake: The legendary English privateer whose final campaign reveals the limits of his bluster. Driven by a desire for gold, national glory, and royal favor, he finds his luck exhausted, his tactics anticipated, and his mind tormented by failure before dying of dysentery.
• Sir John Hawkins: Co-commander of the fleet whose stubborn refusal to accommodate Drake's miscalculations breeds immediate ranker. Weakened by illness early in the voyage, he dies off the coast of Puerto Rico before seeing the expedition fall completely apart.
• Thomas Maynarde: An insightful land officer whose narrative strips away romantic myth. He observes the pettiness of the commanders, laments the poorly trained crews, and records Drake's tragic private confessions as the fleet breaks down.
• Don Pedro Tello & Spanish Commanders: The defenders of Puerto Rico who organize an aggressive defense. By scuttling ships to block the channel and fortifying shorelines, they preserve two million in silver for their king.

In Its Own Voice

"...he never thought any place could be so changed, as it were from a delitious and pleasant arbour into a wast and desarte wildernesse..."

Maynarde recalls Drake’s private despair as bad weather, lack of plunder, and tropical disease dismantle his lifelong assumptions about the Spanish Main.

"...never shippe of Her Majestie’s went so vilely manned out of her kingdom; not twenty of them worthy to come into her shippes..."

Maynarde vents his frustration at the incompetence of the English gunners and crew during a chaotic naval engagement against Spanish forces.

"...it might be without advantage to learn, from the example of one so justly celebrated as Drake, what sordid motives may be cloaked under the pretence of national glory..."

The Hakluyt Society's preface sets a sober tone, framing the document as a necessary corrective to blind hero-worship.

What It's Really About

Underneath the naval action, the text exposes the corrosive nature of vanity and greed masking as patriotic duty. Maynarde’s account dismantles the romantic myth of Elizabethan privateering, portraying it as an ill-managed, speculative venture where leaders prioritized personal honor and plunder over logistics and troop welfare.

The text also highlights the clash between mythic expectation and harsh tactical reality. Drake relies on past glory, expecting the Caribbean to yield easy riches as it once did. Instead, he encounters an empire that has learned to defend itself through naval blockades, warning systems, and fortified garrisons. The narrative ultimately questions the wisdom of reckless expansion, showing how hubris, divided leadership, and systemic unpreparedness lead to total collapse.

Why Read It Today

This volume offers a refreshing, unvarnished look at maritime history that stands in stark contrast to sanitized historical fiction. Readers who enjoy naval history, primary historical sources, or anti-heroic perspectives will appreciate Maynarde's sharp, sarcastic observations and the rare inclusion of official Spanish reports detailing the exact same events.

The text presents some friction for modern readers: Elizabethan spelling variations, archaic nautical terminology, and period-typical religious and national prejudices require light patience. The inclusion of administrative rosters, ship orders, and Spanish military despatches slows the narrative pacing at times. However, these raw elements preserve the authentic atmosphere of sixteenth-century seafaring. The emotional core of the book—watching a famous hero come to terms with his own mortality and failure in a remote corner of the world—remains surprisingly moving and modern.