Hurricane Gilbert devastates Jamaica; it turns towards Mexico's Yucatán Peninsula two days later, causing an estimated $5 billion in damage.

Hurricane Gilbert was an extremely powerful tropical cyclone that formed during the 1988 Atlantic hurricane season, which peaked as a Category 5 hurricane. The storm brought widespread destruction to the Caribbean and the Gulf of Mexico, and is tied with 1969's Hurricane Camille as the second-most intense tropical cyclone to make landfall in the Atlantic Ocean, it was also the second most intense tropical cyclone on record in the Atlantic basin in terms of barometric pressure, only behind Hurricane Wilma in 2005. Gilbert was also one of the largest tropical cyclones ever observed in the Atlantic basin. At one point, its tropical storm-force winds measured 575 mi (925 km) in diameter. In addition, Gilbert was the most intense tropical cyclone in recorded history to strike Mexico.

Jamaica is an island country in the Caribbean, covering 10,990 square kilometres (4,240 sq mi). It is the third-largest island in the Greater Antilles and the Caribbean, after Cuba and the island of Hispaniola. Jamaica lies about 145 km (78 nmi) south of Cuba, 191 km (103 nmi) west of Hispaniola, and 215 km (116 nmi) southeast of the Cayman Islands. With 2.8 million people, Jamaica is the third most populous Anglophone country in the Americas and the fourth most populous country in the Caribbean. Kingston is the country's capital and largest city.

The Yucatán Peninsula is a large peninsula in southeast Mexico and adjacent portions of Belize and Guatemala. The peninsula extends towards the northeast, separating the Gulf of Mexico to the north and west of the peninsula from the Caribbean Sea to the east. The Yucatán Channel, between the northeastern corner of the peninsula and Cuba, connects the two bodies of water.