The most recently developed island for tourism in the Hawaiian archipelago may be the smallest, but with that petite size comes exclusivity. In the past few decades, the former pineapple plantation island of Lanai, just 9 miles (14km) across the channel from Maui ©, has become a luxury playground that still has much of its precious local flavor intact. When you stay on Lanai, you get the sublime feeling that this Hawaiian island belongs to you—at least for a week or so.
The state tourism board has given Lanai the sobriquet of “Hawaii’s Most Enticing Island,” because Lanai (140 sq. miles/363 sq. km, with 18 miles/29km of unspoiled sandy beaches) is basically the private province of the guests who can pony up the cash to stay at its two five-star resorts—there aren’t many other accommodations options here. (Many say that Lanai really “arrived” as Hawaii’s enclave for the rich when Bill Gates rented out the Manele Bay resort for his 1994 nuptials.) In exchange for the hefty price tag of your hotel room, you’ll have free rein of the island’s outdoor activities (hiking and four-wheeling to the heights of Lanai are de rigueur, along with swimming and exploring along the 47-mile/76km coast) and an intimate window on local life in the island’s one and only town, Lanai City. Lanai City was originally the village that supported the workers of the Dole Pineapple Plantation (closed in 1992), and some institutions there, like the Lanai Plantation Store (aka Lanai City Service), which is ground zero for island gossip and groceries, feel like a time warp.
On the southern side of Lanai, Hulopoe Bay has one of Hawaii’s best all-around beaches, a stunning crescent of golden sand backed by palms, picnic facilities, and clear, cobalt blue water great for snorkeling in summer. Nearby is one of the island’s two luxury resorts, the Four Seasons at Manele Bay ; the other property is also a Four Seasons, the inland, plantation-style Lodge at Koele Beachcombers should head to Shipwreck Beach, on the northeast coast, a windswept stretch of sand unsuitable for swimming but with evocative remains of the many vessels that have foundered offshore over the years.
Running for 7 miles (11km) up and over the top of Lanai’s highest point, Mount Lanaihale (3,368 ft./1,027m), the Munro Trail is a must for hikers or off-road vehicles, and provides wonderful views of neighboring Maui. Perhaps Lanai’s most unique and unusual sight is the so-called Garden of the Gods at Keahiakawelo, a garden of strange rock stacks set amid a barren landscape; come at sunset for the best color and light effects. Lanai also has two championship golf courses, attached to the two resorts; the oceanfront Challenge at Manele course was designed by Jack Nicklaus, while the upcountry Experience at Koele course is a Greg Norman masterpiece incorporating tropical geography and lofty views.
If you don’t care to spend Four Seasons levels of money for the privilege of overnighting on Lanai, you can also visit the island as a day trip from Maui with the 45-minute passenger ferry from Lahaina (much easier than flying from Maui). Unless you’re going with an organized tour group, it’s best to get a rental car with four-wheel-drive upon arrival in Lanai and a good map or set of directions from a local: Most of Lanai’s best attractions are at the end of unmarked or dirt roads.