In 1492, Columbus sailed the ocean blue … and totally missed his mark. His journey may not have gone exactly as planned, but there were some interesting detours along the way. 

1. THE CANARY ISLANDS 

When Columbus set sail from the Spanish port of Palos on August 3, 1492, he already had his first pit stop planned. The Niña, Pinta, and Santa Maria headed to the Canary Islands off the coast of Morocco for last-minute preparations and restocking. It's a good thing, too. By the time they arrived, the Pinta's rudder had disconnected and the ship was taking on water. (Columbus suspected some of the crew had second thoughts about the voyage and sabotaged the vessel.) There was talk of leaving the ship behind—but what were they going to do, order another one online? The men repaired the Pinta during the layover and officially headed west on September 6. 

2. SAN SALVADOR ISLAND 

We know Columbus—or perhaps a sailor on the Pinta named Rodrigo de Triana—first spotted land on October 12. But what we don't know is where exactly they were. Not that there's anything wrong with that—Columbus thought he was in the East Indies! The island was definitely in the Bahamas and already inhabited by the Taino people, who called it Guanahani. Columbus named it San Salvador and recorded that it was "very flat and with very green trees" with a surrounding reef and laguna in the middle. A number of islands fit the description, but many scholars later agreed that it was probably what used to be known as Watling Island. The Bahamanian government renamed it San Salvador Island in 1925. 

3. CUBA 

Columbus didn't stay put for long. After naming the small surrounding islands Santa Maria de la Concepcion, Fernandina, Isabela, and Las Islas de Arena, the fleet took off again. On October 28, Columbus and his men arrived in what they believed to be China—but was, in fact, Cuba—most likely through the Bay of Bariay. Columbus christened the island Juana after Queen Isabella's son and soon discovered the joys of tobacco. Long before Cuban cigars, the Arawaks smoked with Y-shaped nostril pipes. 

4. HISPANIOLA 

After China, which was actually Cuba, Columbus set off for Japan. The trip was no pleasure cruise: On Christmas Day, the Santa Maria ran aground after hitting a reef. Columbus ordered his men to dismantle the ship and build a temporary fort called Villa de la Navidad with some "help" from the locals. Columbus headed back to Spain on the Niña a few weeks later, leaving 39 sailors behind on La Isla Española, with his mistress's cousin Diego de Arana acting as governor. When Columbus returned a year later, the fort was destroyed and all of the men were dead. Today, Hispaniola is one of only two shared Caribbean islands, split between Haiti and the Dominican Republic. 

5. SANTA MARIA ISLAND

The journey back to Spain was miserable. After a number of storms, the crews of the Niña and Pinta disembarked in the Baía dos Anjos on Portugal's Santa Maria Island around February 15. Columbus set off seeking boat repairs while half his crew went to church (presumably to thank God they were still alive). Alas, the locals were wary of strangers after numerous pirate attacks and quickly arrested the sailors. So first Columbus lost the ship Santa Maria, and then he almost lost half his crew on Santa Maria. Fortunately, he was able to reason with the Portuguese to get the sailors released, plus to get some boat repairs. Then they finally headed home.   

6. DOMINICA 

Columbus didn't have much to show for his adventures when he returned to Spain, but he quickly secured funding for a second voyage. Returning to the fort on Hispaniola was his first priority, but he got a little distracted. On November 3, 1493, Columbus spotted a heavily forested island and had to take a look-see. The Kalinago natives weren't very welcoming—and the Europeans thought they were cannibals—so Columbus quickly named the island Dominica and headed out to explore the neighboring tiny islands, including modern-day Antigua and Montserrat. Why did he call this new place Dominica? Because it was Sunday (Domingo in Spanish) and, if you haven't noticed by now, Columbus wasn't especially original in the naming department. 

7. JAMAICA 

Columbus was horrified when he finally returned to Hispaniola and found La Navidad in shambles. He and his men built a new settlement called La Isabela, which was later struck by two of the earliest hurricanes ever observed in North America in 1494 and 1495. But before the natural disasters, Columbus made his own trouble by mistreating the locals and alienating his fellow sailors, who were hungry, sick, and mutinous. When they failed to find gold, Columbus headed back to Cuba and soon found his way to St. Ann's Bay in Jamaica. The Taino natives were hostile, so Columbus continued exploring and landed at Discovery Bay, Montego Bay, and Portland Bight. He didn't find gold in Jamaica, either, so he went back to Hispaniola before returning to Spain. 

Columbus later returned to—well, was shipwrecked in—Jamaica on his fourth voyage in 1503 after losing his four-boat fleet in a series of storms. He and his men were stranded for a year, until captain Diego Mendez rowed a canoe to Hispaniola. By that point, Columbus wasn't even allowed to visit Hispaniola, and it took months of negotiations before Mendez could charter a rescue caravel. 

8. TRINIDAD

Back to the chronology! The King and Queen allowed Columbus to go on a third voyage in May 1498 to resupply the colonists on Hispaniola (before he was blacklisted) and find a new trade route. The six-ship fleet split up: three went to Hispaniola and three went to new islands. Columbus chose the latter, of course. He and his men had almost run out of drinking water when they spied three peaks in the distance. Columbus named the land Trinidad and quenched his thirst in the Moruga River. 

9. VENEZUELA 

Contrary to what many people believe, Columbus did not discover America. But he did reach South America on August 1, 1498. As he and his men gathered water in Trinidad, they spotted the coast of South America. They explored the Gulf of Paria for eight days, discovering the "Pearl Islands" of Cubagua and Margarita and reaching the Orinoco River in Venezuela. Ever wrong about geography, Columbus admired this verdant new land and concluded he'd reached the Garden of Eden. Sigh.