Photos by Ashlea Deahl A view of Hulopoe Beach from the Four Seasons Manele Bay

This quaint, peaceful Hawaiian island has two distinct personalities, and you’ll love them both.

Twenty minutes after making cautious kitten steps along the edge of a craggy cliff that overlooks swirling tides of teal and foamy white, I’m navigating a trail deep into a cool, damp forest, my shoes caked with sherbet-colored mud. Within the hour, my heavily shaded path will clear of the drippy pines, fragrant eucalyptus and steely ironwoods that shelter it, revealing a sunny gulch in the foreground and a patchwork of silhouetted islands in the distance.

This is Lanai, the smallest of Hawaii’s inhabited islands at just 140 square miles and perhaps the most unique of them all. With two distinct topographies, climates and personalities all on one baby of an island, Lanai is a bit of a conundrum to travelers seeking that quintessential Hawaiian vacation. Within 20 minutes, a quick elevation shift alters the air from damp to dry and the scenery from tropical to woodland. Perhaps it’s this dichotomy that keeps the island out of the spotlight compared with its bigger, more tourist-laden siblings. And the little more than 3,000 residents of Lanai would like to keep it that way,

This isn’t to say Lanai locals don’t welcome visitors. On the contrary, the amiable island folk are happy to show you the secrets of their land, of which there are many. But before digging too deep, it’s best to get to know this petite island paradise and its past lives.

Untouched by humans until the 1500s, Lanai has endured a handful of incarnations – first as a battleground of sorts between native Hawaiian kahuna (priests), who scorched the land in a fiery standoff to see who could keep their flame burning longer. The ashen soil never recovered, creating a porous, moon-like terrain that still blankets much of the island (visit the Garden of the Gods for a close-up view of the ancient war zone).

Lanai’s second life came with the reign of King Kamehameha I, who brought the Hawaiian Islands together to form one royal monarchy in 1810. His favorite fishing retreat, a sacred village called Kaunolu, is now a National Historic Landmark.

a hike to “Sweetheart Rock” reveals swirling tide pools below.

Influence from the western U.S. is evident in the island’s third stage, when the island was purchased and transformed into a giant working cattle ranch. While most ranching activities have ceased today, its history is still alive and well, most notably at the Four Seasons Lanai, The Lodge at Koele, a rustic but refined resort in the heart of Lanai City.

Once the center of the island’s cattle ranching operations, this plantation-like property evokes the ambience of a quaint country manor but with touches of modern opulence throughout (rates run $350-$675 per night).

Surrounded by towering Cook Island pines, which were first planted on the island by former ranch manager George Munro, and sprawling green hills that disappear into a dense forest, the resort is nestled roughly 1,000 feet higher than the island’s sea level, creating a cool, dry setting, much like Prescott, rather than the expected tropical nature of Hawaii. But fear not – you’ll still feel oceans away from Arizona. Championship golf, horseback riding at the Stables at Koele, lawn bowling, clay shooting and croquet lend to the resort’s stately ambience, and the nearby 12.8-mile Munro Trail takes you on a tour through some of Lanai’s most inspiring scenery.

Dedicate a full day (and plenty of water) to hiking this trail, which leads to Lanai’s highest scenic point, Lanaihale, where you’ll find the stunning Maunalei gulch mentioned earlier and views of Maui, Molokai, Kahoolawe, Hawaii’s Big Island and Oahu in the distance.

Four Seasons, The Lodge at Koele

Lanai’s most recent incarnation is perhaps its most well known. For much of the 20th century, Lanai was under the stewardship of James Dole, who transformed the island and its fertile land into the world’s top grower and exporter of pineapples, earning it the nickname “Pineapple Isle” and propelling it into the proverbial produce hall of fame forever.

The rising cost of growing the sweet fruit eventually sent operations overseas, but Dole left his mark on the island for good. Dole Park serves as a gathering point for locals in Lanai City, and the historic Hotel Lanai once housed Dole’s managers and VIP guests. (This is your most modest option for accommodations, with rooms starting at $125 per night.)

Present day Lanai is much more laid back than its workhorse history might imply, with most of the island’s income stemming from tourism dollars. But as Hawaiians are known to do, the legends of its past are weaved into every attraction, activity and business. And, with only 30 miles of paved roads and not a traffic light in sight, this small island has maintained a small-town image and a “far, far away” feel.

Getting there is a bit of an adventure in itself. After flying into Maui, you’ll either catch a quick second flight into Lanai Airport or a 40-minute ferry ride from Maui’s Lahaina Harbor to Manele Harbor on Lanai’s southern coast.

It’s here that you’ll get your first glimpse of Lanai as you might imagine a Hawaiian island to be – flawless cobalt-blue waters gently lapping up to the harbor’s rocky edge, thick blades of green island grass underfoot, and fluorescent flora dotting the landscape.

The setting only gets richer as you head another mile or so into the island, where you’ll find one of only three resorts on Lanai and the only one with a beachside property, the Four Seasons Resort Lanai at Manele Bay (rates run roughly $445-$945 per night).

This luxurious resort fronts a marine preserve, promising views of playful spinner dolphins, stoic green sea turtles and a rainbow of colorful reef fish, all of which you can see up-close when you book a sailing, snorkeling or scuba diving trip with Trilogy Ocean Sports or Spinning Dolphin Charters of Lanai.