Massive Hurricane Ivan slammed into Cuba's sparsely populated western tip with the worst of its 160-mph eyewall and moved into the Gulf of Mexico, threatening U.S. oil installations and prompting thousands of Americans to flee its catastrophic strength. Five Florida counties urged or, in some cases, ordered residents to leave Tuesday as Ivan spun out of the Caribbean, where it cut a deadly swath through Grenada, Jamaica, the Cayman Islands and Cuba. Ivan, one of the fiercest storms ever recorded in the region, pounded the heartland of Cuba's famed cigar industry Monday and smashed giant waves onto Grand Cayman island. It smashed away part of a hotel on Cayman's famed Seven Mile Beach, seen in the fly-over of an AP-chartered aircraft over the island Monday. The storm has killed at least 68 people in seven islands or countries the Caribbean, devastated Grenada and badly battered Jamaica's Negril resort. Millions more people are threatened. There were no immediate reports of deaths, injuries or serious damage in Cuba.