Which Hawaiian Island Is Right for You?
Thanks to the just-approved Southwest flights now making it possible to go from mainland U.S. to Hawaii for less than the cost of dinner, America’s most isolated state is becoming a new vacation option for many. But which island(s) to visit? Should you start with the family-friendly resorts of Maui? Or seek out poke on Oahu?
Even if your vision of the Aloha State is based solely on 1961’s Elvis Presley–starring Blue Hawaii—which both created enormous vacation demand here, and also much of the island chain’s pop culture image—know that you have many options. Seven of the eight major landmasses amid the 130 or so islands are inhabited, and six are primed for tourists. (The seventh, Niihau, is only open to those who know the island's owners.) There's an island for everyone—and for every age and stage of Elvis. Here’s a need-to-know primer to help you plan your next trip to the Hawaiian islands.
GettyOahu
Nickname The Gathering Place
Its Elvis personality Unabashedly showbiz, rhinestone jumpsuit Elvis
Best for Shoppers and North Shore surf seekers
Island Story Almost everyone will visit Oahu, either in transit or as a destination, since this island is home to the biggest city and hub airport, Honolulu; Pearl Harbor, of course, is also on Oahu. It was the shorefront neighborhood of Waikiki where that 1960s tiki culture first emerged post-Elvis: an invention, with little connection to indigenous culture, it still lingers in a few spots—try the grill at the Outrigger Reef Waikiki Beach Resort. The modern sport of surfing was also workshopped here local boy Duke Kahanamoku who would go on to export his childhood hobby of riding a papa nui board over the waves, to California and beyond.
Island Signatures Don’t miss Shangri La, heiress Doris Duke’s mansion-turned-museum on Waikiki’s tony Diamond Head. Take a break from the urban energy and kitsch by visiting the North Shore, where the seven miles of breaks are some of surfing’s most challenging and exciting waters anywhere in the world—the Banzai Pipeline will be familiar from any extreme video.
Where to Stay Families are raving about Aulani, a Disney Resort and spa outpost that opened in 2011. Or you could lean into the kitsch of Waikiki’s heyday at the Shoreline, originally built as flight attendant dorms and rebooted as a trippy, Day-Glo fever dream a few months ago. Then there’s the 315-room Queen Kapiolani, which reopened last October after a $35 million renovation, also intended to recapture its midcentury heyday.
GettyMaui
Nickname The Valley Isle
Its Elvis personality The King at the height of his fame—everyone's a fan
Best for Families and first-timers
Island Story Picture Hawaii in your mind, and you’re probably seeing Maui, the figure-of-eight-shaped island with attractions that act much like the state’s greatest hits. There are superb beaches (33 miles of them), rocky cliff-faces, lush rainforests, and the surrounding waters teem with marine animals. Hawaii’s historic culture is also palpable: The stone foundations of the ancient places of worship, known as heiau, are here—the largest is Pi'ilanihale Heiau in the Kahanu Garden.
Island Signatures Head offshore to Molokini, and swim or snorkel in the water there—the tiny landmass is in fact the crater of an extinct volcano. Dress warmly to watch the spectacular sunrise from Mount Haleakala, almost 10,000 feet above sea level.
Where to Stay Try one among the several spots in tony Wailea: The adults-only Hotel Wailea, a Relais & Châteaux property, was rated no. 1 in the state during last year’s Readers' Choice Awards.
GettyThe Big Island
Nickname The Big Island, though it’s officially, albeit confusingly, called the island of Hawaii
Its Elvis personality Outdoorsy, enlisted Sergeant Presley
Best for Lava chasers over sunbathers
Island Story The Big Island is synonymous with the volcanoes that once created every island of what’s now Hawaii, bubbling up from the ocean floor. Most of the lava flows elsewhere are dormant, but Kilauea here remains active. Indeed, it made headlines in 2018 for its aggressive eruption, though has settled down since then. The surrounding 505-square-mile Hawaii Volcanoes National Park has reopened so you can once again head there to see the expanded Halema’uma’u crater, which doubled in size after the eruption, or hit the popular Steam Vents or Sulphur Banks trails.
Island Signatures Don’t come to the Big Island for the beaches—most are man-made spots so it isn’t renowned for sunbathing (one notable exception: the eminently Instagrammable green sand beach of Papakolea). Instead, plan to hike one of its five national parks or explore the volcano with a boat trip, where you’ll often surrounded by dolphins and manta rays.
Where to Stay Plan ahead for the reopening of the Mauna Lani, Auberge Resorts Collection, which is currently undergoing a multimillion-dollar renovation to reboot later this year. Until then, the just-renovated Westin Hapuna Beach is the best option.
GettyKauai
Nickname The Garden Isle
Its Elvis personality Actual, Blue Hawaii-filming Elvis
Best for Film fans and nature lovers
Island Story Geologically the oldest of the islands, and the first to be inhabited, this is a favorite for Hollywood—quite literally, as it’s been used in movies as a stand-in location for everything from Australia to Tahiti. A go-to backdrop for Spielberg, who shot Jurassic Park, Raiders of the Lost Ark and Hook here, it was also where Elvis filmed Blue Hawaii. Today, Kauai draws a cool Angeleno crowd, including Lisa Bonet and Alicia Keys, to its astonishing beaches. You might also run into Mark Zuckerberg, who sunk more than $100 million of his Facebook-made fortune into a local compound to great local opposition.
Island Signatures Its nickname is apt, as this is the lushest, greenest of the chain. Indeed, you can only reach one-fifth of the island on foot or in a car, so plan to hire a helicopter or boat if you really want to explore. Book an open-door flight over the cliffs and valleys of the Nā Pali coast or join a kayak tour to paddle round to its isolated beach.
Where to Stay The Elvis Presley Foundation was rumored to be buying Coco Palms, a pioneering luxury resort made famous by Blue Hawaii before it fell derelict, though that deal didn’t go through. Instead, it’s undergoing a slow renovation toward a much-delayed, developer-led reopening, now promised for 2020. While you wait, the Readers’ Choice Award favorite the Princeville Resort Kauai is a lovely alternative.
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GettyLanai
Nickname The Pineapple Isle
Its Elvis personality TCB-era Elvis, ensconced in his own plush, private jet
Best for Celebs and privacy seekers
Island Story Was it $300 million? Or $600 million? Reports differ on quite how much it cost Oracle founder Larry Ellison to snap up 98 percent of this island, the erstwhile heart of the Dole pineapple empire. That was seven years ago, and since then, the billionaire has funneled even more money into transforming it into a real-life Fantasy Island.
Island Signatures Privacy and exclusivity—no wonder Oprah, Will Smith, Cindy Crawford, and Tom Cruise have opted for vacations here. Take a jeep out to reach Hulopoe Beach, or to hike to Lanaihale, the island’s peak.
Where to Stay There are two distinctly different Four Seasons here: the Lodge at Koele in the fog-wreathed hills, which has been rebooted as a wellness sanctuary, and the oceanfront resort on Manele Bay, close to Rupert Murdoch’s island hideaway. Book into either of these, and you can transit in Honolulu airport via their own, luxury lounge, so the experience begins before you set foot on Lanai.
Ed FreemanMolokai
Nickname The Friendly Isle
Its Elvis personality Barefoot, pre-fame Elvis, back home in Tupelo, Mississippi
Best for Digital detoxers and those looking for a secret island getaway
Island Story Just 8,000 people live around this 400-square-mile island, a remote spot best known for a sad chapter in its history: It was here that those suffering from Hansen’s disease (once known as leprosy) were exiled from the 1860s until after World War II; the law was only rescinded in 1969. Now that spot is Kalaupapa National Historical Park.
Island Signatures A hip-swaying sleepiness. There’s only one town here, Kaunakakai, and no stoplights, little traffic, or noise other than the waves. Pack hiking boots to explore spots like Halawa Valley, kayak out off the south shore to explore the fringing reef, or take up a perch on the often-deserted, three-mile long Papohaku beach.
Where to Stay Molokai is alone in the tourist-focused islands in that no big name resorts and hotels operate here, so decompress in a room at Hotel Molokai—the best are the ones cooled by the trade winds rather than air conditioning.
