Lanai's history as a Dole pineapple plantation still shapes life here today. The main places to stay, Hotel Lanai and the Lodge at Koele, were originally built in the cool green "up-country" to house Dole's visiting VIPs. Lanai City—a misnomer, given that it's essentially just one square block surrounded by shops, restaurants, a jail, a school, and a rickety movie theater—was also centered here for easy access by plantation workers. To this day, there's not a single stoplight and very little crime because, as the chief of police jokes, "There's nowhere to run." The rest of the 13-mile-wide, 18-mile-long island is largely undeveloped. Castle & Cooke, which owns the island and almost everything on it, has spiffed things up all around since Four Seasons took over management.
WHEN TO GO
As in the rest of tropical Hawaii, the weather in Lanai typically varies fewer than 15 degrees between summer (June to August: average high 85° F) and winter (December to February: average high 78° F), and both seasons are pleasantly warm. Because of holiday breaks, the summer and winter months are the busiest times for Hawaii as a destination in general, so you'll find the best deals and fewest crowds in the spring and fall shoulder seasons. Unlike the other islands, Lanai never really feels crowded, but because of limited accommodations, it's always best to book ahead. Due to its rich plantation history, this is where you'll find the annual Pineapple Festival, which includes competitive pineapple eating and cooking contests, held in Lanai City every summer (usually in July). In September, the Aloha Festival showcases music, dance, and history in numerous locations statewide.
HOW TO GET THERE
Lanai has a small airport 10 minutes from Lanai City and 25 minutes from Manele Bay, in Puuwai Basin (at one time, the world's largest pineapple plantation). Hawaiian Airlines (800-367-5320; www.hawaiianair.com) and Island Air (800-652-6541; www.islandair.com) serve Lanai via connections on Oahu and Maui.
Most people, locals and tourists alike, arrive on Lanai on the Expeditions Ferry, which operates between Maui and Lanai; it runs five times daily and takes about 45 minutes (800-695-2624 or 808-661-3756; www.go-lanai.com).
Rent a jeep to see the most fascinating parts of the island. Lanai has a mere 30 miles of paved roads, and much of its rugged, beautiful terrain is accessible only with the help of four-wheel drive. Dollar Rent a Car has a monopoly on rental cars on Lanai, so the ride will cost you (800-800-4000 or 808-565-7227; www.dollar.com). It makes sense to rent a vehicle only on the days you're planning to off-road; on other days, a free hotel shuttle runs regularly throughout the day between the Lodge at Koele, Hotel Lanai, and Manele Bay. A word of caution: Road quality on unpaved sections varies greatly due to rains and traffic, so if a track seems impassable, it likely is. And a tow is expensive.
For brochures, maps, guides, and general information about Lanai, contact the Lanai Visitors Bureau (431 Seventh St., Suite A, Lanai City; 800-947-4774 or 808-565-7600; www.visitlanai.net; closed Saturdays and Sundays) or Hawaii Visitors and Convention Bureau (800-464-2924 or 808-923-1811; www.gohawaii.com).