With no inhibiting factors to strengthening, Gilbert quickly became a hurricane late on September 10 and then a major (Category 3) hurricane on the 11th. It moved consistently west-northwest influenced by a strong high pressure system to its north. This movement led to the hurricane's first landfall in Jamaica. The eye passed completely over Jamaica on September 12 with 125 mph (205 km/h) winds and a central pressure of 960 mb (28.35 inHg), making it a Category 3 hurricane on the Saffir-Simpson Hurricane Scale.
Gilbert strengthened rapidly after emerging from the coast of Jamaica. As the hurricane brushed the Cayman Islands a reporting station on Grand Cayman recorded a wind gust of 156 mph (252 km/h) while the storm passed just to the southeast on September 13. Extreme intensification continued until Gilbert reached a minimum pressure of 888 mb (26.22 inHg) with sustained flight-level winds of 185 mph (295 km/h), having intensified by 72 mbar in a space of 24 hours. This pressure was the lowest ever observed in the western hemisphere and made Gilbert the most intense Atlantic hurricane on record, until it was surpassed by Hurricane Wilma in the 2005 season.
Gilbert made landfall for a second time on the island of Cozumel and then in Mexico's Yucatán Peninsula on September 14 as a Category 5 hurricane, making it the first Category 5 to make landfall in the Atlantic basin since Hurricane David hit Hispanola nine years earlier in 1979; the minimum pressure at landfall in Cozumel was estimated to be 900 mb (26.6 inHg). The storm weakened quickly while crossing land before emerging into the Gulf of Mexico as a Category 2 hurricane. Gilbert restrengthened rapidly, however, and made landfall for a final time as a Category 3 hurricane near La Pesca, Tamaulipas, on September 16.
On September 17 Gilbert brushed the inland city of Monterrey, Nuevo León before taking a sharp turn to the north. The storm spawned 29 tornadoes in Texas on September 18 before moving across Oklahoma and being absorbed by a low-pressure system over Missouri on the 19th.
| Country | Deaths |
|---|---|
| Mexico | 225 |
| Jamaica | 45 |
| Haiti | 30 |
| Guatemala | 12 |
| Honduras | 12 |
| Dominican Republic | 5 |
| Venezuela | 5 |
| United States | 3 |
| Costa Rica | 2 |
| Nicaragua | 2 |
| Total | 341 |
American journalist Jules Siegel was living in Puerto Morelos, Quintana Roo, (near Cancún) with his family. The hurricane hit Puerto Morelos dead-on, but the entire town population was evacuated to Cancún. Siegel's account of this experience was published in a local newspaper in Spanish and is available in English on his website
35,000 people were left homeless and 83 ships sank when Gilbert struck the Yucatán Peninsula. 60,000 homes were destroyed, and damage was estimated at between $1 and 2 billion (1989 USD). In the Cancún region, a further loss of $87 million (1989 USD) due to a decline in tourism was estimated for the months October, November and December in 1988. Rainfall in the Yucatán Peninsula peaked at 13.78 inches in Progreso, Yucatán.
In northeastern Mexico, heavy rains in and around Monterrey caused tremendous flooding. More than 100 persons died when five buses carrying evacuees were overturned in the raging floodwaters. Rainfall in northeastern Mexico peaked at over in localized areas of inland Tamaulipas.
Oklahoma recorded the highest measurement of rainfall in the United States, 8.6 inches, in Wichita Mountain Wildlife Refuge. Isolated locations in Texas and Oklahoma reported over , while moderate rainfall of up to fell in central Michigan.