El Golfo de Bien Tiempo
On May 9, Christopher sailed to the 'Gulf of Good Weather'. Yes, you know it, it is now called Montego Bay ;-). From there he sailed back to Cuba, with a beautiful experience called Xaymaca -but no gold- in his pocket.
Later that year he returned and explored the south coast.

In spite of the fact Christopher thought Jamaica was the most beautiful island he ever saw, it took nine years before he came back on the island. His third voyage to the New World brought him to South America and Hispaniola, but not to Jamaica.

Still seeking for a passage to Asia, he met Jamaica again on his fourth -and final- voyage. But some things were changed. On his trips to the New World so far he did not found any gold, ivory or other valuable stuff to trade. The Spanish authorities got impatient he was out of favor. And, besides that, his ships were -thanks to the worms- fallen apart...

Teredos
The first ship Christopher lost was the Gallega, in front of the coast of Panama, Central America. It literally was eaten by the worms (teredos). The second one sank on its way to Hispaniola (which now are Dominican Republic and Haiti). Christopher tried to get back to the coast of Hispaniola, but he did not make it.
Storms forced him to seek a save harbor as soon as possible and finally he found a shelter in Bahía Santa Gloria, Jamaica.

But even there they were not lucky. The two ships left were too much affected by the worms. Columbus and his crew had to get off the boats quickly and watched the sinking of the ships from the beach of St. Ann's Bay.
Although, that is one story. Another tells the ships ran aground in stormy weather at Maima, the place where Columbus first met Jamaica.
Which story is right you want to know? We don't know, but fact is that Columbus got here on land for the second time.