Cleo weakened to a Category 1 hurricane before hitting southern Cuba on August 26. It crossed the island quickly. Shortly after emerging from the north coast of Cuba, Cleo restrengthened to a hurricane, having weakened to a tropical storm while over Cuba. Cleo managed to intensify to a 100 mph (160 km/h), Category 2 hurricane before hitting the Miami, Florida area on August 27. It weakened to a tropical storm while over Florida on the 28th. The center moved offshore between Jacksonville and St. Augustine, Florida, before moving back onshore near Savannah, Georgia on August 29 without any increase in intensity. Its northward path along the Florida coast was unusual for the month of August.