After striking Jamaica the following day, rapid intensification occurred once again, and the storm became a Category 5 hurricane on the Saffir-Simpson scale with peak 1-minute sustained winds of 185 mph (298 km/h), late on September 13.

After landfall, Gilbert weakened rapidly over the Yucatán Peninsula, and emerged into the Gulf of Mexico as a Category 2 storm on September 15.

As a result of the extensive damage caused by Gilbert, the World Meteorological Organization retired the name in the spring of 1989; it was replaced with Gordon for the 1994 hurricane season.

The origins of Hurricane Gilbert trace back to an easterly tropical wave—an elongated low-pressure area moving from east to west—that crossed the northwestern coast of Africa on September 3, 1988.

Over the subsequent days, the wave traversed the tropical Atlantic and developed a broad wind circulation extending just north of the equator.

The system remained disorganized until September 8, when satellite images showed a defined circulation center approaching the Windward Islands.

The depression proceeded toward the west-northwest, and while moving through the Lesser Antilles near Martinique, it gained enough strength to be designated as Tropical Storm Gilbert.

Passing to the south of Dominican Republic and Haiti, it became a hurricane late on September 10 and further strengthened to Category 3 intensity on the Saffir–Simpson scale the next day.

At that time, Gilbert was classified as a major hurricane with sustained winds of 125 mph (201 km/h) and a minimum barometric pressure of 960 mbar (960 hPa; 28 inHg).

On September 12, the hurricane made landfall on the eastern coast of Jamaica at this intensity; its 15 mi (24 km)-wide eye moved from east to west across the entire length of the island.

[7] Gilbert re-strengthened rapidly, however, and made landfall for a final time as a Category 3 hurricane near La Pesca, Tamaulipas on September 16, with winds of about 125 mph (201 km/h).

[3] On September 17, Gilbert brushed the inland city of Monterrey, Nuevo León before taking a sharp turn to the north.

[10] Once Gilbert entered the Gulf of Mexico on September 15, hurricane watches were posted for the portion of the shore between Port Arthur and Tampico.

[10] Texas governor Bill Clements issued a decree allowing municipalities to lift laws in the name of public safety, including contraflow lane reversals[11] and speed limits.

[17] In St. Lucia, heavy rains peaking at 12.8 in (330 mm) in Castries resulted in flash flooding and mudslides, though no major structural damage was reported.

Roughly 5 in (130 mm) of rain fell in Barbados, leading to flash floods and prompting officials to close schools and government offices.

[18] The U.S. Virgin Islands experienced widespread power outages and flooding, with many residents losing electricity for several days.

[17] In Venezuela, outflow bands from Gilbert produced torrential rain which triggered widespread flash floods and landslides in the northern part of the country, killing five people and leaving hundreds homeless.

[23] Heavy rains from the outer bands of Hurricane Gilbert triggered significant flooding in the Dominican Republic and Haiti.

[14] Hurricane Gilbert produced a 19 ft (5.8 m) storm surge and brought up to 823 millimetres (32.4 in) of rain in the mountainous areas of Jamaica,[25] causing inland flash flooding.

[20] Prime Minister Edward Seaga stated that the hardest hit areas near where Gilbert made landfall looked "like Hiroshima after the atom bomb.

[28] Reconnaissance flights over remote parts of Jamaica reported that eighty percent of the homes on the island had lost their roofs.

[29] Gilbert passed 30 miles (48 km) to the south of the Cayman Islands early on September 13, with one reported gust of 157 mph (253 km/h).

[15] Across parts of northern Central America, heavy rains from the outer bands of Hurricane Gilbert triggered deadly flash floods.

[39] As Gilbert lashed the third largest city of Mexico, Monterrey, it brought very high winds, torrential rains, and extensive flash floods.

Among these were a paramedic and a pregnant woman who died when a Mexican Red Cross ambulance fell into a flooded arroyo near Los Chorros after a bridge collapsed.

40 tornadoes were spawned in an area from Corpus Christi and Brownsville north to San Antonio and west to Del Rio.

[44][45] Gilbert also provided a good look at a particular unusual hurricane-spawned tornado in Del Rio, two hundred and fifty miles from the ocean.

[46] Oklahoma recorded the highest rainfall in the United States at 8.6 inches (220 mm), in Wichita Mountains Wildlife Refuge.

[57] In Jamaica, dance hall DJ Lovindeer released a single called Wild Gilbert a few days after the storm.