Lay of the Land
Nine miles west of Maui, Lanai was the last major Hawaiian island to be colonized and the last to be discovered by tourists. It has been privately owned since 1922, when the Dole Food Company bought the 141-square-mile island for $1.1 million and turned it into the state’s – and eventually the world’s – largest pineapple plantation. In 1987, David Murdock, chairman of Dole Food at the time, decided to grow a resort paradise on the island instead of pineapples. In the 1990s, Murdock reportedly spent $400 million to build two hotels (one on the beach and one up country) that are now managed by Four Seasons. One has views of palms; the other of pines. Each has its own championship golf course, beautifully landscaped gardens and an impressive collection of art and antiques.
In June 2012, Oracle CEO Larry Ellison bought the island of Lanai… 98% of it, that is. The remaining two percent belongs to the state and to private citizens, some of them descendants of pineapple workers. Ellison has big plans for Lanai, including improving infrastructure and supporting sustainable agriculture. (Ellison’s purchase follows years of interest in Lanai from high-profile names. Bill Gates took it over for his wedding, and a number of years ago, he allegedly offered to buy half the island but Murdock refused.)
The two hotels, Four Seasons Resort Lanai and The Lodge at Koele (also managed by Four Seasons and currently closed) are only a 20-minute drive apart, but they offer starkly different experiences. Four Seasons Resort Lanai sits above the island’s prettiest beach and emphasizes sun, sand and sea. The Lodge at Koele is surrounded by pine groves up in the mountains and resembles a lodge in the Pacific Northwest.
Beyond the resort areas, Lanai has a small town (sweetly named Lanai City) with a few cute cafés, and miles of remote areas only reachable via off-roading. If you long for a deserted beach, hiking trail or mountaintop, you need only choose your mode of transportation: jeep, bike, boat, horseback or foot. In terms of activities, there are water sports, including scuba, boating, snorkeling and surfing; tennis; golf; hiking; horseback riding; as well as helicopter and catamaran tours, all of which can be arranged through the Four Seasons.
What there is not is any kind of nightlife. This is a sleepy island with a small resident population (around 3,100), some of whose families were once plantation workers and now work directly or indirectly for the resorts. There’s a very lazy, laid-back quality to the island despite the high-powered visitors.
When to Go
The weather is good all year. However, if you want to see whales, the time to come is between November and March when pods come to breed in the channel between Lanai and Maui and you are virtually guaranteed daily whale sightings.
From Oahu: The most direct way is to take a 40-minute commuter or charter flight from Honolulu. The commercial flights do sell out quickly though so it’s wise to book them early.
From Maui: Travelers based on Maui can take the ferry from Lahaina harbor, which takes about 45 minutes. There are multiple ferries each day to and from Lahaina. You are riding with day trippers, backpackers and those coming from Lanai to grocery shop on Maui, so it’s a local scene. Also, during whale migration months (December – April), the scenic ferry crossing can turn into a mini whale watch.