Now mostly owned by software tycoon Larry Ellison, the second smallest inhabited island in Hawai‘i used to be the world’s largest pineapple exporter. Today, the former “Pineapple Isle” is known for its ultra-luxurious hotels, small shops and cafes along Dole Park, and miles of secluded beaches.
First settled in the 1500s, Lana‘i later became a favorite fishing spot of King Kamehameha the Great. Rent a 4x4 or hire Rabaca’s Limousine (559.0230) to visit Keomoku, a plantation-era ghost town on the rugged east side.
In the island’s cool uplands, enjoy customized wellness packages at the new adults-only Four Seasons Resort Lodge at Koele, a Sensei Retreat (1 Keomoku Highway, 800.505.2624). At beachfront Four Seasons Resort Lana‘i (1 Manele Bay Road, 565.2000), savor the views, along with 18 holes on the Jack Nicklaus-designed golf course. Tropical artwork at Mike Carroll Gallery (443 Seventh St., 565.7122) includes designs benefiting the Lana‘i Cat Sanctuary (1 Kaupili Road, 215.9066, lanaicatsanctuary.org), a popular open-air shelter/ cat cafe.
Casual-chic Lana‘i City Bar & Grille (828 Lana‘i Ave., 565.7212) hosts live music on weekends.
Sleepy Moloka‘i has remained staunchly rural and deeply rooted in Hawaiian culture. Among its natural wonders: the world’s tallest sea cliffs and a 28-mile-long fringing coral reef, which is the longest in Hawai‘i.
From 1866 to 1969, Hawaiian law banished residents with Hansen’s disease (once known as leprosy) to isolated Kalaupapa Peninsula. The Catholic Church later canonized two saints, Damien and Marianne of Moloka‘i, for their selfless care of the exiles.
Only guided tours grant visitors access to Kalaupapa National Historical Park, which can be reached by a hike or mule ride (567.6088) down the 1,700-foot cliffs, trail permitting; short flights can also be arranged. On the lush East End, hiking tours of private Halawa Valley (542.1855) begin with traditional Hawaiian protocol and include a dip in an enchanting waterfall pool.
Find solitude and the best sunsets at 3-mile-long Papohaku Beach on the island’s west side.