If you're looking for nightlife, Lanai may not be your best choice. Alternately known as Hawaii's "Most Secluded Island" and "The Pineapple Island" (it once hosted the world's largest pineapple plantation), Lanai is home to a mere 5,000 residents — the vast majority of whom live in the cool heights of Lanai City overlooking the vast, red-dirt fields below.

What Lanai lacks in discos it more than makes up for in outdoor adventure. Not far from Lanai City you'll find the Munro Trail, which climbs from the city's 1,600-foot elevation through stands of Norfolk pines (planted in the early 1900s by New Zealand naturalist George Munro) and up to the highest point on the island, Lanaihale ("house of Lanai"). From this point at 3,370 feet five other islands are visible on a clear day.