If you're looking for nightlife, Lana'i may not be your best choice. Alternately known as Hawai'i's "Most Secluded Island" and "The Pineapple Island" (it once hosted the world's largest pineapple plantation), Lana'i is home to a mere 5,000 residents — the vast majority of whom live in the cool heights of Lana'i City overlooking the vast, red-dirt fields below. With only 17 miles of paved roads, beautiful Lanai is one of the best kept secrets of the Hawaiian Islands and the least visited.
On Lana'i you have the best of both worlds - an undeveloped Hawaiian Island and a couple of world class hotels. This island paradise shelters all kinds of unexpected treasures - exploring the rain forests, sunset strolls along the beaches, and ancient monuments. Some of the not-to-be-missed excursions on Lana'i are Shipwreck Beach (a great place to comb for treasures with a backdrop of a reefed ship), Kaunolu Bay (an ancient fishing village where you can look for petroglyphs) and Hulopoe Bay (the best snorkeling spot in the Hawaiian chain). In all, Lana'i has over 100 miles of unpaved roads for treking and exploring.