The Misadventures of Christopher Columbus

Four voyages can lead to plenty of misadventure. Discover the places where Christopher Columbus met with high drama (and just a few setbacks) during his discovery of the New World, from 1492 to 1504.
By: Lisa Singh
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Photo By: Thinkstock

Photo By: Thinkstock

Photo By: Thinkstock

Photo By: Randy Lemoine through through flickr Creative Commons

Photo By: Wikimedia Commons

Photo By: Thinkstock

Photo By: Thinkstock

Photo By: Thinkstock

Photo By: Thinkstock


Christmas Day 1492 wasn’t all glad tidings and good cheer for Christopher Columbus. On a journey to the northern coast of the Caribbean island of Hispaniola, one of Columbus’ 3 ships, the Santa Maria, ran aground and had to be abandoned. It was the first of Columbus’ 4 voyages to the Americas.

Bay of Arrows

Columbus didn’t exactly get a warm welcome when he landed on the Samana Peninsula (in present-day Dominican Republic). He met with violent resistance from the Ciguayos, one of the nations of the Caribbean islands. Because of the Ciguayos' use of arrows, Columbus called the inlet where he encountered them the Bay of Arrows. Historians have since debated its exact location: Some say it is the Bay of Rincon, others that it is Samana Bay.


The good times kept on coming as Columbus headed for Spain, on the last leg of his first voyage. He soon had to put those plans on hold, as a storm forced his fleet into Lisbon. There Columbus anchored next to Portugal King John II’s harbor partrol ship. Columbus spent the next week in Portugal, before he was able to continue on to Spain.

La Navidad

Nine months later, Columbus once again set sail for the high seas. This time, on his second voyage, he returned to Hispaniola, where he intended to visit the fort of La Navidad (built during his first voyage). However, Columbus discovered that the fort, located on the northern coast of Haiti, had been destroyed by the native Taino people. Centuries later, in 1977, an amateur archeologist excavated artifacts from La Navidad.

La Isabela

It seemed like a good idea at the time. When Columbus sailed more than 60 miles eastward, along Hispaniola’s northern coast, he established the settlement of La Isabela, in present-day Dominican Republic. But in 1494 and then, in 1495, the settlement was struck by 2 North Atlantic hurricanes. Hunger, disease and mutiny soon followed, until Columbus abandoned the settlement altogether.

Cuba ... Part of Asia?

That's what Columbus was thinking when he arrived in Cuba (which he named Juana) on April 30, 1494. Exploring the island’s southern coast, Columbus placed his bets that it was part of a peninsula connected to mainland Asia.

Gulf of Paria

And this must be the Garden of Eden! That’s what Columbus concluded as he sailed the Gulf of Paria (between present-day Trinidad and Venezuela). The nice climate, the abundance of food, the friendliness of the natives and the richness of the area’s natural resources all led him to that conclusion. He also wagered that, based on the rotation of the pole star in the sky, the Earth must not be perfectly spherical, but rather bulged out like a pear around the new-found continent we now know as South America.

Tropical beach, Hispaniola

Columbus wasn’t feeling so well when he returned to Hispaniola on Aug. 19, 1498, during his third voyage. He felt even worse when he discovered that many of the Spanish settlers of the new colony were in rebellion against his rule, saying that Columbus had misled them about the supposedly bountiful riches of the New World.

Santo Domingo

Columbus’ fourth and final voyage met with choppy waters in June 1502. When his fleet arrived in Santo Domingo, it was denied port by the new governor. But Columbus got his revenge. He told the governor a storm was coming. The gov didn’t listen … to his demise. He ended up surrendering to the sea, along with 29 of his 30 ships.

Belen River, Panama

Columbus’ 4 ships took a bruising while cruising through present-day Panama. Locals had told Columbus about gold and a strait to another ocean. Columbus set out on an exploration and established a garrison at the mouth of Panama’s Belen River. In April 1503, one of Columbus’ ships became stranded in the river. Meanwhile, the garrison was attacked by the Guaymí locals. Further headaches followed when shipworms damaged the ships at sea.

St Ann's Bay, Jamaica

Columbus’ ships sustained further damage when a storm hit off the coast of Cuba. Unable to travel on, the fleet was beached in St. Ann’s Bay, in Jamaica. For 1 year, Columbus and his men remained stranded in Jamaica before help arrived. In all, Columbus’ voyages stretched over 12 years, and -- a few misadventures aside -- opened the door to the “New World."

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