Indagare Matchmaker: The Best Hawaiian Island

From privately owned Lanai to bustling Oahu, Hawaii's five main islands all offer unique experiences—our expert outlines which is the best Hawaiian island for you.


[caption id="" align="alignnone" width="620"]Beach in Oahu Hawaii Courtesy Hawaii Tourism Authority, Tor Johnson[/caption]

Hawaii’s most populous island is also its top destination for innovative restaurants, music and culture. Some of the state’s best-known locations, like white-sand Waikiki, Pearl Harbor and the North Shore, with its famously fearsome waves, are here.

  • Best Island for: Travelers who want to spice up their beach time with some urban energy, and history buffs, who will enjoy the only royal palace in the United States, the Pearl Harbor Memorial and the midcentury haunts of Hollywood legends
  • Where to Stay: Waikiki offers easy access to the best shopping and nightlife, but you may opt for a little more serenity in luxe resorts just outside town.
  • Keep in Mind: Although pristine beaches and excellent hiking are only a few miles from Waikiki/Honolulu, roads are gridlocked during commuting hours. Drive at off-peak times.
  • Special Spots: Pearl Harbor Museum, Diamondhead, North Shore
  • Favored Activities: Dining, nightclubbing, museumgoing, shopping, surfing.


[caption id="" align="alignnone" width="620"]Double waterfall in Kauai Hawaii Courtesy Hawaii Tourism Authority, Tor Johnson[/caption]

Hawaii’s northernmost island feels a little wilder than its southern neighbors, as even its luxury accommodations often have a bohemian vibe. Hikers are drawn to the startling Napali cliffs, while surfers relish the stellar, and less crowded, waves.

  • Best Island for: Adventure seekers, who will appreciate Kauai’s world-class hiking and surfing, as well as opportunities to kayak, snorkel and sail
  • Where to Stay: Hanalei Bay and quaint Hanalei town, located at its midpoint, beckon with their relaxed vibe. Just above, Princeville is home to the area’s only luxury resort.
  • Keep in Mind: Kauai’s 432 inches of annual rainfall make it the wettest and coolest Hawaiian island. Its south side, near Poipu, is dryer.
  • Special Spots: The ten-mile-long Waimea Canyon, the “Grand Canyon of the Pacific,” and the fantastical Napali cliffs, best seen by boat or helicopter
  • Favored Activities: Hiking, surfing, yoga, kayaking, snorkeling

The Big Island

[caption id="" align="alignnone" width="620"]Pool at Four Seasons Resort Hualalai in Hawaii Courtesy Four Seasons Resort Hualalai[/caption]

The largest island in the Hawaiian archipelago is still growing, thanks to a continually erupting volcano. Cattle ranches, coffee plantations and the charming Victorian houses of drizzly Hilo remind visitors of an earlier era, while the oft-snow-capped peaks of Mauna Kea and Mauna Loa overlook eleven climate zones.

  • Best Island for: Travelers who like to seek out authentic experiences and get a feel for the lifestyle and history of a place
  • Where to Stay: The warm Kona-Kohala coast has several all-inclusive resorts, but to live like a local, spend some time in the wet, wee state capital, Hilo.
  • Keep in Mind: The Big Island’s most fascinating attractions, like its lava fields and the Mauna Kea summit, are more than two hours by car from the Kona-Kohala coast.
  • Special Spots: Hawaii Volcanoes National Park and the Maunakea Visitor Information Station
  • Favored Activities: Walking alongside lava, stargazing, examining Polynesian petroglyphs, viewing the sacred ground of ancient Hawaiians


[caption id="" align="alignnone" width="620"]Outdoor lounge area with firepit at night at Four Seasons Resort Maui at Wailea Courtesy Four Seasons Resort Maui at Wailea[/caption]

With its hillside mansions, ultraluxurious resorts, gleaming beaches and dramatic topography, Maui takes your breath away. Manicured gardens decorate the sunny south, while mountains, lush forests and rugged coasts grace other areas.

  • Best for: Those whose idea of a perfect vacation is being pampered at a world-class spa and sipping top-shelf cocktails at a posh pool scene.
  • Where to Stay: Wailea is home to some of the island’s most renowned resorts and spas. For pampering without the bling, consider staying in Hana.
  • Keep in Mind: Although poolside lounging, celebrity chef restaurants and ultraluxe accommodations may be all you need, Maui’s striking natural splendors beg to be explored.
  • Special Spots: Hana, Haleakala National Park, Wailea spas
  • Favored activities: Tennis, spa treatments, water sports, browsing art galleries, whale watching


[caption id="" align="alignnone" width="620"]Horseback riders on trail near Courtesy Four Seasons Lodge at Koele in Hawaii Courtesy Four Seasons Lodge at Koele[/caption]

Privately owned for nearly a century and a half, the 140-square-mile island has belonged to Oracle CEO Larry Ellison since 2012. The (reportedly) $600 million island boasts two Four Seasons, tiny Lanai City, pristine coastal waters and forested upcountry terrain.

  • Best for: People who want to get away from it all and so don’t mind the lack of nightlife and urban action
  • Where to Stay: The Four Seasons Lanai
  • Keep in Mind: If you’ve come to Lanai for quiet seclusion, be sure the hotel isn’t hosting a corporate retreat during your visit.
  • Special Spots: Hulopoe Bay, where spinner dolphins swim, and Garden of the Gods, where natural lava sculptures adorn the red earth
  • Favored Activities: Golf, horseback riding, clay shooting, hiking, exploring by jeep

Published onJanuary 20, 2018

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