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  • Writer's pictureJacob Hansen

The Story of Columbus Pt 3: Attempting Settlement- The 2nd Voyage (1493-1494)

Updated: Apr 12, 2022



In September of 1493, about six months after he returned to Spain from his first voyage, Columbus set sail with an entire fleet. He was now an admiral overseeing 17 ships and 1200 Spaniards consisting of laborers, aristocrats, adventurers and artisans. The plan was to establish a permanent trading settlement in the new land and many Spaniards had joined this armada in hopes of getting their own share of these new lands which were said to be rich in gold. Columbus on the other hand was still very much dedicated to his vision of discovering the Great Khan so that he could validate his theories and to hopefully establish the trade route and alliances needed in order to retake Jerusalem to save Christendom and the world. In typical feudal fashion, Columbus sailed under the express orders of the crown to acquire new lands for Spain and to make Christians vassals of peaceful native peoples. The cannibals and those who resisted were to be subjected by force or enslaved. So with the goals of the Spanish crown and his own personal goals in mind he set sail with this large number of people and ships along with his brother and recently baptized Taino godson Diego who would act as an interpreter and diplomat to the tribes they encountered.



Columbus crossing on this second voyage is one of the great historical feats of navigation and seamanship. He had heard rumors from the natives on his first voyage about islands that were closer to Spain. So with the prospect of a shorter crossing he intended to try and reach them. Incredibly, that is what he did! He sailed his fleet of 17 ships safely and in an astounding 21 days, from the familiar seas off the Canary Islands across thousands of miles of open ocean to the easternmost islands of the Caribbean. It’s the same route sailors have used ever since. To this day, a 21 day crossing is excellent time even for modern sailors. Columbus, the newly christened “Admiral of the Ocean Sea”, was able to navigate his way to a group of small islands thousands of miles away based entirely on reports from local natives whose language he did not know. Further, he did so without any major incident. His fleet sighted the islands around Dominica, on November 3rd of 1493. Immediately, everyone was struck by the incredible beauty of the islands, but their streak of good luck was about to end.


Island Hopping the Eastern Caribbean. (Nov 1493)

Dominica Present Day

Columbus had come upon what, to this day, is considered by many mariners to be the most desirable sailing destination in the world. The turquoise waters and palm covered islands with tall mountains rising up from the Eastern Caribbean Sea are breathtaking and the winds and weather are steady most of the year. However, Columbus' fleet had stumbled into islands that were inhabited by a very different group of natives than the peaceful and curious Taino people he met on his first voyage. As they began exploring the islands between Dominica and Puerto Rico, toward were he had left the men from his first voyage, they were shocked by what they found. A doctor on the 2nd voyage wrote in his journal about the experience.


“These people raid the other islands and carry off all the women they can take, especially the young and beautiful, whom they keep as servants and concubines. They had carried off so many that in fifty houses we found no males and more than twenty of the captives were girls. These women say that they are treated with a cruelty that seems incredible. The Caribs eat the male children that they have by them, and only bring up the children of their own women; and as for the men they are able to capture, they bring those who are alive home to be slaughtered and eat those who are dead on the spot. They say that human flesh is so good that there is nothing like it in the world; and this must be true, for the human bones we found in their houses were so gnawed that no flesh was left on them except what was too tough to be eaten. In one house the neck of a man was found cooking in a pot. They castrate the boys that they capture and use them as servants until they are men. Then, when they want to make a feast, they kill and eat them, for they say that the flesh of boys and women is not good to eat. Three of these boys fled to us, and all three had been castrated.”— The Four Voyages of Christopher Columbus: Being His Own Log-Book, Letters and Dispatches with Connecting Narratives. (Classics Book 217)



While the natives on the first voyage had been nearly entirely peaceful, the Spaniards on this second voyage must have had a very different impression. They would come across village after village and often would have skirmishes with the hostile tribes that ended in prisoners being taken. However, Columbus worked hard to make peace with any natives he found. He even took Carib prisoners and, after giving them gifts, clothes, and food, would return them back to their people to try and show they wanted peaceful interactions. But the skirmishes continued as they sailed their way through the eastern Caribbean Islands heading toward Haiti (Hispaniola) where Columbus had left 40 men behind at the end of his first voyage. During these encounters Caribs would often flee at the sight of the Spaniards and leave behind captured Taino women that were being held as sex slaves. Columbus took these women aboard and treated them well and did his best to get them back to the Taino people. They even recorded finding an abandoned baby, who they believed was being held as future food. Columbus writes about taking in this baby and doing their best to care for it.


One sad episode during this portion of the voyage happened after one of the many skirmishes. After a fight, the Spanish took prisoners, both men and women. One of these women was placed under the charge of one of Columbus’ close associates, Michelle de Cuneo. A letter which is alleged to be written by Cuneo was discovered in the 1880s. It describes how he raped one of these women. However, the historical records in no way concludes that Columbus knew about this ghastly act of barbarism.


Arrival and Horror. (Dec 1493)


After almost a month of island hopping north and west, they reached the island of Haiti (Hispaniola) and began to approach the area they called "La Navidad" where Columbus had left his men eight months earlier. Their excitement turned to horror when they found a dead body near one of the rivers along the shore. They could see the dead body was that of a man with a full beard. Knowing the natives grew almost no facial hair, they feared the worst. When they finally pulled into the bay where Columbus had left his forty men eight months before, they were horrified to find that all that remained was the charred wood of the fort mixed with human bodies. All 40 men (including some related to Columbus), were dead. The Spanish were struck with both grief and outrage. Columbus now was surrounded by 1200 Spaniards looking for justice.


Luckily, Columbus did not lose his composure and immediately sent for his native friend from the last voyage, Chief Gaucanagri. He came to Columbus and told him that he had done all he could to protect his men and was even wounded trying to save them. Guacanagri said that the Spaniards Columbus left behind had gone inland looking for gold and began making off with local women from a rival tribe. The Chief of that tribe, a warlike chief named Caonabo, declared war on the foreigners and despite Guacanagris attempt to defend them the entire crew were killed by Caonabo and his warriors.



Needless to say, the Spanish were outraged. They had just spent the last month dealing with almost nothing but hostile natives and now found out all of their countryman left from the first voyage had been killed. Many doubted Gaucanagri’s story, especially when it was apparent that the “wound” he claimed to have suffer defending the Spaniards was fake. Despite this, Columbus believed his friend Guacanagri and so, in order to defuse the tensions, he decided they should find a new place to settle that was not so close to Gaucanagri’s village.



La Isabela- The First Settlement. (Dec 1493 to Feb 1494)


The bay at La Isabella, where Columbus' Fleet Anchored

Columbus' fleet sailed east along the northern coast of Haiti for about 50 miles to a new spot in a large bay. The 17 ships unloaded and the 1200 settlers and adventurers began constructing a town that Columbus named "La Isabela" after the queen of Spain who had championed his vision. Almost immediately, Columbus ran into challenges. The working class on the voyage were willing to get their hands dirty with the building of the town but the Spanish aristocrats (known as Hidalgos) felt it was beneath them and wanted natives to be their servants and do the work for them. Columbus was annoyed by their laziness. To further complicate matters, sickness began to break out amongst the settlers. Within a month, it was reported that about 1/3 of the settlers are so sick they couldn't work. Still, throughout December 1493 to February 1494 the small town begins to take shape.


Modern Ruins of "La Isabela"

During this warm winter of settlement construction, Columbus decided to send out an expedition to begin searching for the gold in the interior that Guacanagri had told Columbus about. Columbus appointed an ambitious young 28 year old officer named Alonso De Ojeda to take a scouting party to go inland to search for gold and to seek where they might be able to establish a mining operation. Ojeda and his group pushed into the interior of the island into a large valley on the other side of the mountains where they landed. By working with the natives, they eventually found a place that seemed to have abundant gold. The natives refered to the region as “The Cibao” (which is a large valley in the northern regions of the modern Dominican Republic). Ojeda returns and reports his findings of gold to Columbus.


Columbus was excited about these reports and believed he was on the verge of producing the needed returns to the King and Queen that would validate their investments in him. Unfortunately, he was dealing with illness and many disgruntled settlers that were unprepared for the rigors and work required in settling new land. Many of the hidalgos would not even eat the local food which was very abundant. When the Spanish food they brought with them started to run low, the hidaglos claimed they were starving. In February, Columbus decided to send back 12 of his 17 ships along with a letter to the King and Queen requesting more supplies. He also sent back Caribs who had been taken prisoner and made slaves from the earlier hostile encounters. Columbus naively hoped that these natives could be brought out of their ways by taking them back to Spain and teaching them Christianity. Christians could not be slaves under the laws of Spain. Thus, through baptism they could be freed and become interpreters and guides for future endeavors. When the ships arrived in Spain, about half of the natives were dead from illnesses to which they had no immunity. Also, almost all of the Spaniards who had come back to Spain were the ones who most disliked Columbus. The dead slaves, the unhappy settlers, and the lack of gold sent back to Spain caused the King and Queen to have concerns about Columbus' management of the enterprise. Still, they sent back the ships with the needed supplies.


Pushing Inland and Building Fort St Thomas (March-April 1494)


In March, Columbus finally decided to make a full blown expedition into the Cibao region to establish a permanent fort so they could begin mining operations. With great pomp they went inland. His men marched in full military form so as to deter any natives from engaging in violence against them. When they arrived in the Cibao valley, Columbus was enthralled with the fertility and beauty of the region. He left 50 men under the command of a military officer named Pedro De Margarit with orders to built the fort which they called fort St Thomas .



After this nearly month-long expedition, Columbus returned to Isabela to find a mess. Sickness was still ravaging the town and 60% of the town was burned in a fire while he was away. He did not even get three days to address these problems when a messenger arrived with news that the new fort and it’s 50 men were being attacked by Caonabo (the same chief who had killed the men left behind on the first voyage). Columbus took decisive action and placed 400 of his most battle ready men under the command of Ojeda (who commanded the first expedition) to put down any native threat. Ojeda was also given orders to relieve Margarit of his command once the natives were quelled. Margarit was then to take the 400 soldiers to continue inland exploration. It was a decision that Columbus eventually came to bitterly regret.


Columbus seemed to be naive about Spanish conquistador culture. For example, as soon as Ojeda went out with these 400 soldiers, some of his men’s clothes were stolen by natives. In a gross overreaction and filled with zealous bravado, Ojeda found the local chief who had the clothes and he demanded them back. The chief refused to return the clothes so Ojeda seized the chief and his entire household and had one of the chiefs men’s ears cut off. He sent the chief and the thieves back to Isabela in chains. Columbus was likely shocked by this but feeling the need to be strong in front of his Spaniard compatriots, he ordered the thieves to be executed. However, this seems to have been a strategic bluff to placate the Spaniards because as soon as the local chief pleaded for the lives of the thieves Columbus let them all go free with a mere promise to not steal again.


Setting Sail in search of the Great Khan. (April-Sep 1494)


In late April 1494, Ojeda was continuing on his march out to the inland fort of St Thomas. Columbus was likely disillusioned with all the headaches of settlement management and decided to put command of the settlement in the hands of others. Columbus likely had little interest in a single settlement and gold operation. He wanted to sail, explore and find the Great Khan in order to save Christendom. The busy work of settlement just seemed to be hindering those plans. So, with his brother Diego and others in charge of the settlement, he prepared his ships and best sailors for an expedition. His goal in this journey was to push farther west than ever before to try and see if Cuba was an island or a peninsula of the Asian mainland.


Columbus began this six month voyage within his second voyage on April 24, 1494 and headed for the southern coast of Cuba. As was found previously, the natives of Cuba were relatively friendly. During an initial encounter with the natives in Cuba, a large island to the south was mentioned. So Columbus set sail in that direction eventually spotting Jamaica. Columbus was enchanted by Jamaica’s beauty and fertility but found no significant signs of gold. So after sailing along the coast of Jamaica he headed back up to the southern coast of Cuba and and continued his push west into unexplored waters. The weather was not good.



Summer is the rainy season in the Caribbean and the hot muggy weather and sudden storms plagued Columbus ships. To make things even worse they found themselves in a maze of small island and reefs. Shallow water was common along the south Cuban coast, making the sailing very dangerous and difficult. Columbus ran aground on more than one occasion but was able to get unstuck. Pushing through the maze of shallow waters in southern Cuba, he was on pins and needles. For weeks he was watching for shallow reefs while dealing with humidity and bad weather. His health began to suffer. Columbus began to have terrible eye pains, fevers, and an inability to sleep. He also found very few natives and the land seemed to be less and less desirable as they continued sailing. Eventually they found some natives who told them that Cuba was an island. It was not the news Columbus wanted on his search for the Asian mainland. Columbus remained skeptical but did not feel he could push on much further.



Columbus almost reached the far western tip of Cuba but the sailing was so miserable, the supplies were so low and with many of the men sick (including Columbus) it was decided the time had come to turn back. The return trip against the wind provided no relief as the sailors pressed on day after day against rain, wind and rough seas. Columbus nearly died on the return voyage but arrived with his haggard crew in the settlement of Isabela in September 1494 after six months at sea. His luck was not about to improve.



K.E

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