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Preston–Somers expedition
Part of the Anglo-Spanish War
Caracas1578.jpg
Venezuela Province coast in the 1570s
Date 29 May – 29 July 1595 (1595-05-29 – 1595-07-29)
Location
Result English victory
Belligerents
 Spain  England
Commanders and leaders
Strength
  • 500 militia
  • 100 cavalry
  • 7 ships
  • 8 ships
  • 500 sailors
  • 300 soldiers
Casualties and losses
  • 500 killed
  • 11 ships burned
80 killed

The Preston–Somers expedition was an exciting adventure that happened during the Anglo-Spanish War in 1595. This war was a long-running conflict between England and Spain. English ships, led by brave captains George Somers and Amyas Preston, sailed to the Spanish Main (the northern coast of South America).

Their main goal was to help another English explorer, Sir Walter Raleigh, who was looking for a legendary golden city called El Dorado. When they couldn't meet up with Raleigh, Preston and Somers decided to go on their own adventure. They explored the coast of what is now Venezuela.

They bravely captured a fort at La Guaira and then made a tough journey through mountains. They managed to surprise the Spanish defenders and took control of the important city of Caracas. Even though they faced many challenges, the expedition was a success for the English. They returned home safely with some valuable goods.

Why Did This Expedition Happen?

England and Spain had been at war for almost ten years. English ships, often called privateers, were attacking Spanish colonies, warships, and merchant ships. These attacks were sometimes ordered by Queen Elizabeth I. Other times, they were like business ventures, where groups of people invested money to share the profits.

In 1595, the expedition led by Amyas Preston and George Somers was one of these ventures. They had several ships, including the Ascension and the Gift. Their main mission was to work with Sir Walter Raleigh. Raleigh was exploring Trinidad and Guiana, hoping to find the famous golden city of El Dorado.

Preston and Somers also planned to attack Spanish towns along the coast. They had 300 professional soldiers with them. Many of these soldiers had already fought against the Spanish in other parts of Europe. Preston was known for his bravery in the battle against the Spanish Armada in 1588. Somers had also gained fame by capturing valuable Spanish ships.

The expedition started from Plymouth, England, on March 12. They met more ships at sea, including Captain Moses Willis's Archangel. As a practice run, they attacked a Portuguese village on Porto Santo island. They successfully took some supplies from the small villages there.

The Journey Begins: Exploring the Caribbean

By May 18, Preston and Somers reached Dominica island. They rested there for six days before sailing south. On May 28, they held a military inspection on Los Testigos Islands. The next day, they reached Margarita Island and landed ashore.

The following day, they explored Coche Island. There, they captured a Spanish ship called a caravel and some pearl fishermen. This turned out to be very useful for getting information.

First Stops: Cumaná and La Guaira

On June 1, the eight English ships arrived near Cumaná in Venezuela. They quickly captured three more Spanish caravels in the bay. When they landed, they found that the townspeople already knew they were coming.

The English then used a clever trick. They demanded a payment (a ransom) from the town. If the Spanish didn't pay, the English threatened to burn the town. This worked, and they got a good amount of food supplies. The English left peacefully the next evening, but they burned the captured caravels.

The English ships then moved further along the coast. They anchored near Macuto, about a mile and a half east of La Guaira. A small group landed and moved inland, staying close to the sea. They soon saw the fortress that protected La Guaira. This fort also guarded the main path to the city of Santiago de León de Caracas, which was further inland.

Somers then brought the rest of the soldiers ashore. They attacked the small fortress of La Guaira by surprise and captured it easily. The Spanish soldiers defending the fort quickly ran away. They immediately warned other Spanish forces about the English presence. The next day, Spanish horsemen from Caracas came down the mountains. They saw that the English had taken over the fort. The English soldiers offered to fight, but the Spanish quickly retreated. The Spanish soon realized that the English were planning to attack Caracas itself.

The Daring Attack on Caracas

The Spanish tried their best to stop the English from reaching Caracas. They gathered their forces along the main road, known as the Kings Highway. Preston and Somers knew that reaching Caracas would be very difficult. The city was far inland, and its defenses were now stronger because the Spanish were aware of the attack.

Caracas was built on a high plain, about 2,500 to 3,000 feet (760 to 910 meters) high. It was about 6 miles (10 km) inland, in a valley protected by the mountains of El Ávila National Park. The highest point on the road was Pico Naiguata, which is over 9,000 feet (2,700 meters) tall. Caracas had a military force made up mostly of local citizens, organized by Governor Diego Osorio Villegas.

Charles Kingley - 1899 Westward Ho! frontispiece
Frontispiece from the novel Westward Ho! (1899 edition), showing the English during their raid on Caracas.

At night, the English quietly left the fort. They knew that climbing the mountains would make them hard to spot. The Spanish were not watching the English closely, which helped Preston and Somers. They marched silently through the rain during the night. A local Indian helped them as a guide. They used a little-known path high in the mountains, staying far away from the main road.

They walked through thick forests in the dark, sometimes having to cut their way through. They stopped by a stream to rest and waited for dawn. They walked near the top of Pico Naiguatá. Then, they marched down through the morning fog. By daylight, they were in sight of Caracas. The English were amazed at their luck. On June 8, at midday, they appeared outside Caracas completely undetected. They had marched six miles through incredibly difficult land. Even better, they had no injuries, only tiredness.

A small part of the city's local defense force was in front of them. But most of the Spanish defenders were still waiting along the main road. Preston and Somers divided their forces into three groups. The main group was in the center, with two smaller groups on the sides. The English expected the Spanish to attack, but they stayed in place.

The English attacked first and forced the Spanish to run away. The Spanish lost one soldier and had several wounded, but the English had no casualties. The rest of the Spanish defenders on the main road were completely surprised. They were in chaos and too late to do anything. The English quickly entered the city with little resistance. Most of the people who weren't fighting had already fled inland.

The governor, Diego de Osorio, was not in the city. A brave, elderly Spanish horseman named Alonso Andrea de Ledesma tried to stop the English by himself. He used only his lance and shield. Sadly, he was shot and killed. Preston admired his courage so much that he ordered De Ledesma to be carried on his shield and buried with honor. The English had secured the city by 3 PM. The Spanish local forces tried to retake the town, but their attempts were not well organized, and they were pushed back.

The English stayed in Caracas for five days. The Spanish offered to talk about a peace agreement. The English demanded a payment of 30,000 ducats (a type of money). The Spanish offered only 2,000, then 3,000. Since this was such a small amount, Preston and Somers began to search the city for anything valuable and take it.

The Spanish then offered 4,000 ducats to save what was left of the town. But Preston and Somers learned from local Indians that the Spanish had sent for help. They were just trying to delay the talks until more soldiers arrived. Preston and Somers were very angry because the Spanish had broken their word. So, the next morning, they burned Caracas and some nearby settlements to the ground. They then left the way they came, taking whatever they could. The Spanish forces, now with more soldiers, entered Caracas soon after the English left. They found most of the city in ruins.

The English returned to La Guaira by noon on June 14, tired but with their valuable goods. The next day, Preston and Somers burned the fortress at La Guaira and destroyed its defenses. They were then ready to leave.

Caribbean Sea, Avila Mt, Caracas Panorama
A wide view from La Guaira (left) taken from Pico Naiguatá, looking towards Pico Oriental. Preston and Somers crossed this area in 1595 to raid Caracas (Right).

More Raids: Chichiriviche and Coro

The next morning, the English left La Guaira and sailed west. On June 16, they arrived near Chichiriviche. Somers led a group in boats and captured three Spanish ships anchored there. They took some valuable items from them before setting the ships on fire. They entered the town easily, but it was too small for a ransom. So, the English continued further west, heading for Santa Ana de Coro.

On June 20, after sailing along the coast, the English saw Coro Bay. Preston led his soldiers ashore by 11 PM. Their target was the town of Coro. This town was located on a coastal plain at the southern end of the Paraguaná Peninsula. The area was famous for being settled by Germans in the 1500s. The town had a small defense force led by Governor Juan de Riberos.

Somers stayed behind with fifty men to guard the ships. But the Spanish soon realized the English were there. They quickly gathered local citizens to stop them. The English tried to attack the town at night. But they ran into a barricade (a barrier) that the Spanish had built. The English attacked bravely, but the Spanish defended strongly and pushed them back at first. The English tried to go around the barricade, but that also failed, and they started to lose more men.

However, with more English soldiers arriving, they launched another attack. They managed to fight their way through the barricade, forcing the Spanish defenders to run away. There was a chase as the English pursued the Spanish, who only managed to slow them down. The English reached Coro itself. After another small fight, they took control of the town the next morning with relatively few losses.

The English held the town, but its buildings were empty. The residents, along with Governor de Riberos, had been warned and had fled inland with their valuable belongings. Preston then ordered the town to be searched and plundered again.

The English held Coro for about two days. As they were preparing to demand a ransom, Preston learned that a rainstorm had hit the English ships. The ropes of Somers's small ship had broken, and it had been carried out to sea. Because of this, Preston ordered Coro to be completely searched and burned. All the buildings, including the church, were destroyed. Preston quickly led his soldiers back to the coast and set sail to find Somers. The next evening, Somers was just outside the entrance to Lake Maracaibo, looking for safety. With the wind picking up, they both decided to leave. With the wind behind them, they headed towards Hispaniola on June 26.

Returning Home: The End of the Expedition

By June 30, the English ships saw Hispaniola. The next day, they anchored off Cape Tiburón to find fresh food. When they continued their journey on July 8, only Preston's Ascension and Somers's Gift were left. The other ships had decided to sail directly home.

Four days later, the remaining ships anchored off Jamaica. They stayed there for a few days before sailing towards the Caymans. They reached Cabo Corrientes, Cuba by July 22. There, they decided to block the port of Havana for a short time. They hoped to capture a few small ships. However, they only captured two small ships, and sickness began to spread. A disease called Dysentery (a severe stomach illness) affected the ships, killing eighty men. Because of this, the expedition ended. They were lucky that the Spanish had not caused them any harm. Not wanting to push their luck further, they headed home to England.

What Happened Next?

Before the English left the Caribbean, they met up with Raleigh's ships, which were also returning from Guiana. They sailed together for a while. In August, they visited Newfoundland to get supplies of fish before crossing the Atlantic Ocean. They arrived safely at Milford Haven in Wales on September 10, without losing any more men. They then counted their valuable goods.

The expedition's success in terms of valuable goods was only moderate. It just about covered the costs, with little extra profit. This expedition was only meant to support Raleigh's search for El Dorado. But it ended up doing much more than it was supposed to. As an independent adventure, it was very successful in terms of military achievements. Capturing Caracas by going through the mountains was a rare and impressive feat. Except for the losses due to sickness, they had very few battle casualties.

A Spanish historian from the 1600s, José de Oviedo y Baños, described what Preston and Somers did. He said it was "a hidden path, rather, an old disused path, used by the native Indians to ascend the mountain. From there down the mountain into the valley of St. Francis, a road so rocky and impassable that it seemed impossible for a human foot to use."

Queen Elizabeth I recognized Somers and Preston for their bravery. She made them knights for their efforts in this expedition and other brave actions during the war with Spain. In 1596, Preston became captain of the Ark Royal and joined Lord Howard in the Cadiz expedition.

After the English left Caracas, Governor Diego de Osorio ordered the city of La Guayra to be walled. He also made the defenses stronger along the Caribbean coast to stop future pirate attacks. He ordered permanent military groups to be stationed in coastal defenses and the main road to Caracas to be fortified.

Lasting Impact of the Expedition

In 1607, Preston and Somers were both involved in the founding of the Colony of Virginia. This included Jamestown, which was the first permanent English settlement in North America. Somers is remembered today as the founder of the English colony of Bermuda, which was then known as the Somers Isles.

The Preston–Somers raid was the only attack Caracas ever suffered during its time as a Spanish colony. This was unlike other coastal cities in the Spanish Main, which were often attacked. This fact was even used in a tourism campaign in 1980 to promote Venezuela as "the best kept secret of Caribbean."

Some historians, especially from Venezuela, believe that Alonso Andrea de Ledesma, the brave elderly horseman who tried to stop the English in Caracas, might have inspired the famous character Don Quixote. This famous novel by Miguel de Cervantes was written almost ten years later. A Venezuelan composer named Eric Colon wrote an opera about him called El Caballero de Ledesma. It premiered on May 5, 1979, at the Teatro Municipal. The 19th-century writer Charles Kingsley used this expedition as the basis for his popular adventure novel, Westward Ho!.

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