It is known as the "Pineapple Isle" because of its past as an island-wide pineapple plantation.

Kamehameha the Great was the founder and first ruler of the Kingdom of Hawaii, and Lanai is said to have been his favorite fishing spot among Hawaii's main islands.

The island flower is the kauna'oa, or native Hawaiian dodder. As beautiful as it is deadly with white cup-shaped flowers, the kauna'oa has earned an ominous reputation as a vampire plant. Lacking leaves and chlorophyll, it is unable to survive on its own, so it winds its slender shoots tightly around the stems of a host plant, sinking in hooks through which it feeds.

Known to locals as Keahikawelo, the Garden of the Gods is a vast natural rock garden featuring large boulders in a spectrum of red, orange, purple and earthen colors, scattered so perfectly that you'd think they were placed by hand. One legend claims that the rocks fell from the gods' gardens in the sky, while another says they hold the spirits of ancient Hawaiian warriors.

There isn't a single traffic light on the entire island, and most attractions outside of the hotels are accessible only by dirt roads that require an off-road vehicle, bicycle, or a good set of hiking shoes.

Lanai is a roughly apostrophe-shaped island with a width of 18 miles (29 km) in the longest direction.

About a half-hour north from Lanai City is Kaiolohia, also known as Shipwreck Beach. This windy, 8-mile stretch of beach has wrecked numerous ships along its shallow, rocky channel. In fact, the hull of a ghostly oil tanker from the 1940s is still beached on Kaiolohia Bay's coral reef.

A marvelous legend is still told of one of Kaka'alaneo's sons, named Kaulula'au, who, for some of his wild pranks at his father's court in Lāhainā, was banished to Lanai, which was said to be haunted by Akua-ino, ghosts and goblins. Kaulula'au outwitted the spirits and drove them from the island, bringing peace to Lanai and restoring the prince to favor in his father's eyes.

The first settlers most likely migrated to Lanai from Maui and Molokai. They established fishing villages along the coast and then spread into the interior, where they raised taro in the fertile volcanic soil.

In 1909, Charles Gay sold the island to William G. Irwin for one dollar. Irwin's title was upheld in the U.S. Supreme Court.