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 Irma
Hurricane Irma's path was such that its impact was both far-reaching and devastating, with landfalls in Antigua and Barbuda, Saint Martin, the Bahamas, Cuba, and the United States, all at major hurricane intensity. Furthermore, the size of the storm system meant that destruction was prevalent even in territories well removed from landfall occurrences.