Things might get a little crazy these coming Wednesdays as we take you on weekly virtual vacations to unexpected, surprising, and sometimes even strange destinations around the world. With that in mind we’ll take it easy on our first excursion, beginning with a destination in the United States – the non-contiguous United States, that is.

Most people can probably only name four Hawaiian islands: Oahu, Maui, Kauai, and of course, the Big Island of Hawaii. But in fact, there are four other main islands in the chain, and they include Kahoolawe (a World War II bombing range), Molokai (a former leprosy colony), Niihau (which is off-limits to anyone but its owners and their guests), and Lanai (the capitol of pineapple production of yesteryear). Today we’ll be focusing on Lanai, the “Pineapple Isle.”

According to Hawaiian lore, Lanai was once home to man-eating spirits. It’s a good thing these ghouls only had a taste for human flesh and not tangy yellow fruit, because after being purchased by James Dole in 1922, the majority of the island was used as the world’s largest pineapple plantation. Lanai is still owned by the chairman of Dole Food Company, so even though the acres of pineapple fields have been reduced you can always think of man-eating spirits when you’re dipping your spoon into a fruit cup.

Lanai only has about 3,100 residents, who for the most part live in Lanai City (the only city on the island) which is located near the geographic center of the red-soiled, comma-shaped landmass. This may be where all the action is in terms of population, but the island really comes to life further afield where jagged rock formations, pineapple plantation remnants, out-of-this-world views await.

But if you want to see everything the island has to offer, you better be able to handle four-wheel drive. There are no stoplights on Lanai, and most of the roads outside of Lanai City are unpaved and course through rough terrain, so we highly advise that you rent an off-road vehicle and go off the beaten path.

North of Lanai City you’ll find the Kanepuu Preserve, a 590 acre nature preserve that lets you explore the rare dry land forest that once blanketed the Hawaiian lowlands. Also to the north is Keahiakawelo, or Garden of the Gods, where the power of centuries of erosion created an otherworldly rock garden that is rife with ties to Hawaiian mythology. If you’re feeling really adventurous, you can make your way to Shipwreck Beach (the name is pretty self-explanatory), but the roads that lead there are unmarked so you need to ask for detailed directions or else you could be spending the night in your rented 4X4.

In southern Lanai lies another natural rock formation called Sweetheart Rock which, like the Garden of the Gods, is connected to Hawaiian legend. But perhaps the best place on the island to immerse yourself in Hawaiian history is Kaunolu Village. Not only was this spot the favorite fishing location of King Kamehameha I, it is also home to the ruins of a sacred temple, ancient rock drawings, and a 60-foot cliff off of which warriors used to jump into the ocean to prove their fearlessness.

There is plenty more to explore on Lanai, so if you’re inspired to pack up and jet off to this habitually forgotten Hawaiian island, pick one of the only three hotels to choose from – two of which are luxury Four Seasons resorts with some of the world’s best golf courses – and fly out to Maui, where you can take a small charter plane or a ferry to the inaugural Wednesday Wanderlust destination.

Steven tried out for The Amazing Race one time and was denied. We're not saying this is why he started this site, but it may have been a contributing factor in his decision to explore the world online and share his travel inspiration with others.

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