Preston–Somers expedition

On 1 June the eight English privateer vessels and the Spanish prize appeared before Cumaná off Spanish Venezuela and seized three more caravels in the bay.[12] Upon landing however they found the residents had been alerted to their presence; the English then decided on a ransom or otherwise threatened to set the town on fire.[17] The ruse succeeded and a modest amount of foodstuffs were acquired from the Spanish following which the English departed in peace the following evening after having burned the caravels.[4]

The English moved further along the main coast and anchored a mile and a half east of La Guaira at a beach near Macuto.[18] They landed a small force and moved inland parallel to the sea and sighted the fortress (present-day Fort el Vigía) that protected the small town but also protected the main gateway to the city of Santiago de León de Caracas further inland.[17] Somers then disembarked the rest of the men onshore and led the force overland. After probing the defences, the English assaulted the small fortress of La Guaira and with complete surprise occupied it with little resistance.[12] The remains of the garrison then fled and immediately warned other Spanish forces in the area of the English presence.[5] The next day in the afternoon a patrol of fifty Spanish cavaliers descended out of the mountains from Caracas and saw that the English had occupied the fort.[4] A number of the musketeers under Captain Roberts emerged from the keep who offered them combat, from which the Spanish then promptly withdrew.[18] The Spanish soon realised the English were going to strike at Caracas itself.[17]

The Spanish did everything they could to bar their advance, so they concentrated their strength along the main road also known as the Kings Highway leading up to Caracas.[10] Preston and Somers knew that getting to Caracas would be a serious challenge since it was much further inland and the defences were strengthened now that the element of surprise had been lost.[17] For the English, getting to Caracas was a huge challenge as it was built on a high plain, at an altitude of between 2,500 to 3,000 feet (800 to 900 m), six miles (10 km) inland within a valley protected by the mountains of El Ávila which is located along the central stretch of the Venezuelan Coastal Range.[13] Caracas itself had a garrison composed mainly of militia having been organized by the governor Diego Osorio Villegas.[15]

Frontispiece of Westward Ho! novel from an 1899 edition showing the English in discussion during the raid on Caracas

At night the English slipped out of the fort and knew that by heading up the mountains they would be difficult to see let alone be engaged. The Spanish however did not maintain close watch upon the English movements and this obviously worked to Preston's and Somers' advantage.[17] Without haste they marched a column undetected through the rain during the night.[1] They had help from a lone Indian whom they used as a guide and were able to advance up a little-known track high into the mountain and kept well clear of the main road.[13] They marched through the thickly wooded slopes in the dark, some of the time having to cut their way through, and halted at a stream for refreshment and waited for dawn. They walked close around the summit of Pico Naiguatá then marched down on through the early morning fog and were within sight of the town by daylight.[15] The English could not believe their luck when at midday of 8 June they appeared unexpectedly outside Caracas completely undetected.[12] They had marched for six miles in impossible terrain, and what's more apart from fatigue there were no casualties.[18] A part of the city's militia had formed in front of them but the majority were still gathered along the main road.[13]

Preston and Somers then formed three groups, the main battle group in the center, and two smaller, flanking forces on either side.[10] The English thought the Spanish would attack, but they remained in place and in turn attacked and forced the Spanish to flee, leaving behind one dead soldier and a number of wounded but the attackers had suffered no casualties.[4] The rest of the militia further up guarding the main road were surprised by the unexpected attack and were in complete disorder and too late to do anything.[5] The English soon entered the city with little resistance encountered since most of the non-combatants had fled inland.[2] In the absence of the governor Diego de Osorio, the mayor of Baruta, a lone elderly Spanish rider named Alonso Andrea de Ledesma bravely attempted to check their progress with his lance and shield; he was however shot dead.[19] So admired for his courageous effort, Preston ordered that De Ledesma be carried on his shield and received a hero's honour before being buried.[20] The invaders had secured the city by 3pm and the Spanish militia attempted to retake the town in poorly coordinated attempts, but were repelled.[21]

The English remained in possession of Caracas for five days and the Spanish offered a parley from which the English attempted a ransom of 30,000 ducats.[17] The Spanish offered 2,000, then 3,000, but being so small Preston and Somers then set about sacking and plundering the place stripping anything of value.[12] A ransom of 4,000 ducats was offered to spare the remains of the town but Preston and Somers soon received intelligence from Indians that the Spanish had sent for help and were delaying the negotiations until reinforcements could arrive.[5][15] Preston and Somers were furious as the Spanish had gone against their honour of a parley and as a consequence in the morning they burned Caracas and some surrounding settlements to the ground.[4] They then departed the way they came taking whatever they could away from the Spanish militia who now had more reinforcements. The militia entered Caracas soon after the English had left only to find the vast majority of it in ruins.[17] The English had returned to La Guaira by noon on 14 June with the booty, exhausted by their arduous trek.[10] The next day Preston and Somers set the fortress ablaze as well as demolishing its defenses and were thus prepared to leave.[21]

Panorama of the view from La Guaira (left) taken from Pico Naiguatá looking at Pico Oriental which Preston and Somers traversed across in 1595 to raid Caracas (Right)

The next morning the English departed from La Guaira and headed West. On the 16th they soon arrived outside Chichiriviche.[22] Somers led a boat party that captured three anchored Spanish vessels and secured some of the booty from them before setting firing to them.[17] The town was entered with virtually no resistance though was too small to make a ransom and the English departed further West, this time to Santa Ana de Coro.[4]

On 20 June, having made their way along the coast the English sighted Coro Bay; Preston led his formation there and ferried all his troops ashore by 11 p.m.[4] Their target was the town of Coro which was established at the south end of the Paraguaná Peninsula in a coastal plain, flanked by the sandy Médanos Isthmus. The area was famous for having been colonized by the Germans as sort of a part payment from the Spanish in the 1520s to 1540s.[23] The town had a small garrison under command of Governor Juan de Riberos.[11]

George Somers

Somers stayed behind with fifty men to secure the anchorage but the Spanish were soon aware of his force and hastily marshalled militia to impede them.[24] The English attempted a night time assault on the town but ran into a barricade which the Spaniards had built prior, blocking their advance.[22] The English attacked in number but the Spaniards defended stoutly, repelled their attack at first, and then tried to advance around the barricade to outflank it but this too failed and losses were beginning to mount.[5] With more men coming up however the English launched another assault and managed to fight their way through, driving the defenders off.[4] There was soon a running fight with the English pursuing the Spaniards, who really only delayed their advance. They reached Coro itself and after another small fight, the town was gained and secured the following morning with relatively few casualties.[24] The English held the town, but its buildings had stood empty as the residents along with de Riberos had received ample warning of the advance and fled inland with their valuables. Preston then ordered the town to be sacked and the English went on the plunder again.[5][25]

Coro was held for about two days and on preparing a ransom Preston had learned that a rain storm had struck the English anchorage.[4] The cables of Somers's fifty man pinnace had parted which was then driven out to sea.[25] Preston therefore ordered Coro thoroughly sacked and torched; all the buildings were destroyed including the church and chapel.[11] Preston hastened his column back to the coast and set sail in order to search for Somers.[26] The following evening Somers stood just outside Lake Maracaibo's entrance seeking safety, but with the wind up they both decided to leave and with wind astern headed towards Hispaniola on 26 June.[14]

By 30 June, the Preston–Somers squadron sighted Hispaniola and next day anchored off Cape Tiburón to search for fresh provisions.[24] When the formation resumed its cruise on 8 July Preston's Ascension and Somers's Gift were the only ones left when the other ships decided to depart for home.[26]

Four days later the remains of the privateer vessels anchored off Jamaica, and remained there for a few days before proceeding towards the Caymans.[5] They reached Cabo Corrientes, Cuba, by the 22nd, and there they decided to perform a short blockade off Havana in an attempt to make a few small prizes.[26] Prizes were short coming with only two smalls ships captured and disease began to take its toll; dysentery raged throughout the vessels having already killed eighty men and soon the expedition was to be terminated.[14] Being fortunate that the Spaniards had not caused any damage and not to chance further luck they headed home to England.[4][12]

In 1607, both Preston and Somers reunited in a way to become involved in the foundation of the Colony of Virginia; specifically Jamestown, the first permanent English settlement in North America on the banks of the James River.[28] Somers is remembered today as the founder of the English colony of Bermuda, then known as the Somers Isles Company, a commercial venture. The Preston–Somers raid would be the only attack that Caracas would suffer in its colonial history unlike other coastal cities on the Spanish Main. This fact was exploited for a tourism campaign in 1980 to promote Venezuela as "the best kept secret of Caribbean".[29]

Some sources (mainly Venezuelan)[19] indicate that the elderly lone rider who resisted the English in Caracas, Alonso Andrea de Ledesma, may have been the inspiration for Don Quixote by Miguel de Cervantes, written nearly ten years later.[20] The Venezuelan composer Eric Colon wrote an opera called El Caballero de Ledesma that premiered on 5 May 1979, in a sold-out Teatro Municipal by the Opera Metropolitana de Caracas. The 19th-century writer Charles Kingsley used the expedition as the basis of his most popular adventure, Westward Ho!.