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The only city on Lanai is Lanai City. For the most part, if one needs something, Lanai City is the only place they will find it.
The scenic Munro and Naha trails travel through the mountains and around the island. The scenic Kaumapalau Highway and Manele Road (highway 440) travels from Kaumapalau Harbor, past the airport, into Lanai City, and south to Manele Harbor. Dole Park in downtown Lanai City is a great place to relax, and it includes a small playground for the kids. The most popular beach on Lanai is Hulupoe Beach at Four Seasons. However, if you want to be somewhere more quiet, Shipwreck Beach near the northern end of the island is the place to be. Accommodations are limited on the island, so make sure you've booked ahead. Rooms for April and December high seasons book up months in advance.