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.
1935 Cuba hurricane
The hurricane caused widespread destruction in areas of the western Atlantic. In Jamaica, the storm's strong winds and heavy rain destroyed roughly 3 percent of the island's banana production and damaged road networks. Damage on the island country totaled to $2.7 million. In Cayman Brac, strong winds damaged infrastructure and crops, though no fatalities resulted. Most of the cyclone's deaths occurred in Cuba, where the storm made its first landfall. The hurricane's effects caused a 100 mi (160 km) wide swath of damage which cut across the country. Strong storm surge destroyed low-lying coastal towns, particularly in Cienfuegos, where numerous homes were destroyed and 17 people died. Across Cuba, the storm caused $12 million in damages and 35 deaths. As it crossed the island, widespread evacuation procedures occurred in southern areas of Florida, heightened due to the effects of a disastrous hurricane which struck less than a month prior. However, damage there was only of moderate severity. Passing directly over Bimini in The Bahamas, the hurricane destroyed nearly half of the island with its large storm surge. There, 14 people were killed. Further north, the storm caused slight impacts in Bermuda and Atlantic Canada, though a person drowned off of Halifax, Nova Scotia due to rough seas. Overall, the tropical cyclone caused 52 deaths and $14.7 million in damages, making it the costliest hurricane of the hurricane season.