1899 San Ciriaco hurricane
Hurricane San Ciriaco set many records on its path. Resulting in at least 3,369 deaths in Puerto Rico, the storm was the deadliest hurricane to hit the island and the strongest at the time, until the Hurricane San Felipe Segundo made landfall in 1928 as a Category 5 hurricane. It was also among the deadliest Atlantic hurricanes ever recorded.
Hurricane Dean
Fifteen countries felt the effects of Hurricane Dean as its path through the Caribbean Sea claimed 42 lives. The hurricane first brushed the Lesser Antilles on August 17, 2007, and as it passed through the interior of the Caribbean its outer rain bands swept over the Greater Antilles. It passed Jamaica as a Category 4 hurricane, and strengthened to a Category 5 storm as it made landfall on Mexico's Yucatán Peninsula on August 21. A second landfall on August 22 was less devastating.