Lanai was once owned by the Dole family, who used its land to produce the majority of the world’s pineapples between 1922 and 1992. Now home to two luxury resorts and notable for its distinctive Cook pine trees, championship golf, and exceptional snorkeling, the Pineapple Island provides real estate options ranging from condos and plantation-style cottages to secluded estates. Its only town, Lanai City, contains two markets, a handful of restaurants and shops, a two-screen movie theater, and one school (preschool through 12th grade). With zero stoplights and a population of around 3,000 residents, the island is known for its calm pace and close-knit community feel.