Some of the smallest of the populated Hawaiian Islands, Moloka‘i and Lāna‘i are the state’s hidden gems. Dramatic landscapes paired with a rich history make for an incredible getaway, while their low visitor numbers allow them to maintain their Old Hawai‘i charm.
The stunning view from Four Seasons Resort Lanai.
Formerly known as the “Pineapple Isle” for housing the largest pineapple plantation in the United States, Lāna‘i is now mostly owned by software tycoon Larry Ellison. The island often feels like two separate worlds: The uberluxurious resorts offer pampering and world-class golf, while the rugged back roads lead to ironwood forests and hikes through native ‘ōhi‘a lehua trees.
The southeastern corner of Lāna‘i is home to Kaunolu Point, where Hawaiian warriors would leap from 80-foot cliffs to prove their bravery. It is now known as the birthplace of the sport of modern cliff jumping, and the Cliff Diving World Championships have previously been held here.
The island’s two most exclusive hotels have a flavor all their own. Four Seasons Resort Lana‘i (1 Manele Bay Road, Lāna‘i City, fourseasons.com/lanai) is a luxury oceanfront resort perfect for the family, while adults-only Sensei Lana‘i, A Four Seasons Resort (1 Keomoku Highway, sensei.com) is a country-style mountain lodge known for its wellness offerings.
An hourlong ferry runs between Mānele Harbor on Lāna‘i to Lahaina on Maui, perfect for those who aren’t staying on the Pineapple Isle to still experience its magic. The ferry ride comes with a front-row seat of Lāna‘i’s rugged southern coastline and, in the winter months, humpback whales are a common sight.
The small community of Moloka‘i has remained deeply rooted in Hawaiian culture while preserving the island’s natural wonders: the world’s tallest sea cliffs and a 28-mile-long fringing coral reef, which is the longest continuous one in Hawai‘i.
Moloka‘i was designated as the coffee-growing region of Hawai‘i by King Kamehameha V in 1865. Today, the rolling hills of Kualapu‘u in the middle of the island are still the place to find a delectable brew of 100% Moloka‘i coffee.
No trip to Moloka‘i is complete without a visit to Kalaupapa, a historic leprosy settlement that held patients in isolation from the world for 100 years. Take in the views of the secluded peninsula 1,700 feet below from Kalaupapa Lookout in Pala‘au State Park. More adventurous travelers can reach the settlement by foot or by donkey on a dramatic descent with 26 switchbacks.
Watch the sunset at the beautiful white sand beach of Papohaku. By night, the 3-mile stretch of sand offers an unbeatable starry sky and the faint glow of Honolulu in the distance.
Photography by: Photo courtesy of Four Seasons Resort Lanai