Here is a possible account from Francis Drake's point of view of his failure to take San Juan, Puerto Rico

 Imagine you are living in the 16th century, when Spain and England are locked in a fierce war for global domination. You are a resident of San Juan, Puerto Rico, a strategic island that guards the entrance to the Caribbean Sea and the riches of the Spanish Empire. You have heard of the exploits of Sir Francis Drake, the most feared and famous English privateer who has raided and plundered many Spanish colonies and ships. You have also heard of his defeat at Lisbon in 1589, when he failed to capture the Portuguese capital from Spain. You wonder if he will ever come to your island, and what will happen if he does.

One day, in November 1595, you see a fleet of 27 ships flying the English flag approaching your bay. You recognize Drake's ship, Defiance, among them. You know he has come with 2,500 men to loot and burn your city. You rush to the Castillo San Felipe del Morro, the massive fortress that protects your harbor. There you join 350 Spanish soldiers and militia who are ready to defend your home. You see Admiral Pedro Tello de Guzmán commanding five frigates in the bay, blocking Drake's entrance. You see Admiral Gonzalo Méndez de Cauzo commanding the forts on land, firing their cannons at the enemy ships. You see Governor Pedro Suárez Coronel leading the troops on the ground, repelling Drake's landing attempts.

You are about to witness one of the most epic battles in Caribbean history, when Drake met his match in San Juan. This is the story of how a small Spanish garrison held off a mighty English invasion, and how Drake's reputation as invincible was shattered by the brave defenders of Puerto Rico.

Francis Drake possible account:

I had high hopes for this voyage. I had been commissioned by Queen Elizabeth herself to attack the Spanish strongholds of Puerto Rico and Panama, where they stored their vast wealth of gold and silver. I had a fleet of 27 ships and 2,500 men, ready to follow me into glory. I had also a personal grudge against the Spanish, who had wronged me and my kin many times before.

I set sail from Plymouth on August 28, 1595, with my friend and fellow commander John Hawkins by my side.

We learned that one of our ships had been captured by a Spanish admiral named Pedro Tello de Guzman near Guadeloupe. He had taken our ship's captain prisoner and tortured him for information about our mission. He then sailed ahead of us to Puerto Rico to warn them of our coming.

We did not let this deter us. We decided to attack San Juan Bay on November 22, 1595. We hoped to surprise them with a swift and daring assault. We tried to land at a cove on the eastern end of San Juan Islet, but we found it too shallow and rocky for our ships. We then turned our attention to the bay itself.

But we were met with a fierce resistance from the Spanish defenders. They had sunk two vessels at the harbour entrance, blocking our way. They also had five frigates and 70 cannons ready to fire at us from both sea and land.

We engaged them in a fierce battle that lasted for several hours. We exchanged cannon fire with their frigates and forts. We tried to board their ships and fight them hand-to-hand. But they fought back bravely and repelled our attacks.

We suffered heavy losses: eight to ten ships sunk or damaged; 400 men killed or wounded; precious ammunition wasted; morale shattered.

We also lost Hawkins, who died of dysentery during the attack. He was my friend and comrade for many years. I mourned his death deeply.

Unable to capture San Juan or its treasure, we retreated from the bay in disgrace.

I felt angry and frustrated by this failure. I had underestimated the strength of the Spanish defences and overestimated my own abilities. I had made some tactical errors that cost me dearly.

I had failed my queen and my country who had entrusted me with this mission. And worst of all, I had failed my men and myself.

I also felt some fear and anxiety about my future. I knew that I had lost many ships and men that would be hard to replace. I knew that I faced more dangers ahead as I sailed for Panama where another Spanish stronghold awaited me.

I wondered if I would ever return home alive, or if I would die at sea, like my dear friend, Hawkins.
But I also felt some hope and faith in God: that He would guide me through these trials; that He would protect me from harm; that He would reward me for fighting against Spain and their cursed inquisition; that He would forgive me for my sins.

Sir Francis Drake passed away on January 28, 1596, at the age of approximately 56. He succumbed to dysentery while anchored off the coast of Portobelo where Spanish treasure ships had sought shelter. After his death, the English fleet withdrew in defeat.

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