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Best Hawaiian Islands for Different Kinds of Travelers

By Amanda Castleman

Apr 17, 2019

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Whether your ideal Hawaiian vacation means time sunning, shopping, or snorkeling, there’s an island for you.

Photo by Erin Kunkel

Whether your ideal Hawaiian vacation means time sunning, shopping, or snorkeling, there’s an island for you.

Will it be lava flows or luxury resorts? Waikiki Beach, Pearl Harbor, or humpback whales? Settle that difficult “which island to visit” question once and for all.

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America’s 50th state keeps travelers spoiled for choice, from Japanese boutiques to Jurassic Park backdrops. Where else but Hawai’i can you freewheel down a volcano, order a ukulele from a master luthier, or lounge on 750 miles of subtropical coastline settled by Polynesians?

However, the islands of Hawai’i are as diverse as the travelers who visit. The archipelago includes a staggering 137 islands, which includes small islets and minor islands, as well as the eight main Hawaiian islands. Each one has its own unique characteristics so we’ve compiled an overview of each Hawaiian island to help you decide which one (or two) to visit.

If you measure its height from the ocean floor, Mauna Kea is taller than Mount Everest.

1. Hawai’i

  • Nickname: The Big Island
  • Highlights: Archeology and history, a visit to NASA-funded Imiloa Astronomy Center on Hawai'is highest peak, whale-watching, volcanoes, and national park hikes

One of the world’s most ecologically diverse places, the state’s youngest and largest island (commonly referred to as the "Big Island") sweeps from a black-sand beach to waterfall-laced rain-forest valleys, lava deserts, and snow-capped mountains. The active Kilauea volcano sits on the flank of massive Mauna Loa. But Mauna Kea wins the world heavyweight title for height, outstripping Mount Everest by 4,500 feet when measured from the ocean floor. Adventurous drivers with four wheel drive can navigate the steep winding road to the summit, famed for its stargazing.

Not in the mood for the high road? Visit the NASA-funded Imiloa Astronomy Center instead. Or go low with a nighttime snorkeling trip to visit giant manta rays as they soar and loop, feeding on tiny zooplankton. Make sure to check out the incredible aerial breaching displays of the 11,000-odd humpback whales that winter offshore, too.

Then finish with a peek into ancient traditions at Puuhonua O Honaunau or Kaloko-Honokohau National Historical Park, where Hawaiians once fished, carved petroglyphs, and used toboggan-like sleds to ride downhill over stones covered in dirt and leaves.

The cliffs and lush trails of Kauai’s Napali Coast are steep and spectacular.

2. Kaua'i

  • Nickname: The Garden Isle
  • Highlights: A quiet, laid-back island full of natural beauty, waterfalls, and long stretches of beach, as well as a chance to learn about ancient traditions and culture and visit quaint small towns.

Lushness and serenity reign on the “Garden Isle,” home to the planet’s wettest spot, Mount Waialeale, averaging 451 inches of rain each year. The town of Poipu and the South Shore tend to be sunnier with more eateries, shops, and water sports.

But Waimea—“the Grand Canyon of the Pacific”—and Napali Coast State Wilderness Park hog the spotlight. Here waterfalls and swift streams sculpt one of the world’s most staggeringly beautiful wilderness areas, threaded with ancient Hawaiian archaeological sites.

Fancy a more accessible cascade? Check out Wailua Falls, a 173-foot veil featured in the opening credits of the 1970s TV hit Fantasy Island. Then contrast that riot of water and vegetation with Polihale State Park, where Hawaii’s longest stretch of beach sprawls over 15 miles and dunes can pile up to 100 feet high.

Find a water hazard you can love on Lanai.

3. Lāna’i

  • Nickname: The Pineapple Island
  • Highlights: A small, uncrowded island with a cat sanctuary, golf courses, plantation architecture, and snorkeling.

Before statehood, the United States recognized the Republic of Hawai’i in 1894 with pineapple entrepreneur Sanford Dole as its president. When it was annexed in 1900, it became a territory, and in 1922, Sanford Dole’s cousin James Drummond Dole bought the island of Lāna’i to expand his pineapple farming empire. In 2012, tech billionaire Larry Ellison bought 97 percent of this island, including two Four Seasons resorts (and their championship golf courses).

These wealthy landlords have allowed the island’s natural charm to coexist with those manicured fairways. Today Lāna’i remains an off-the-beaten-path gem—with an emphasis on “path”: Only 30 miles of the island’s roads are paved, but there are more than 400 miles of rugged trails you can explore by four-wheel-drive vehicle or horse or by hiking. Many lead to the 18 miles of nearly empty beaches that ring Lāna’i and to lovely views of other islands.

You will want a convertible to drive the famed Road to Hana.

4. Maui

  • Nickname: The Valley Isle
  • Highlights: Adventure, biking, black- and red-sand beaches, bodyboarding, cowboys (paniolos), epic driving, gardens, hiking, horseback riding, misty mountains, a national park, nightlife, relaxing, shopping, and windsurfing.

Maui remains the best one-stop sampler of Hawaii’s highlights. The state’s playground is anchored by the dormant Haleakala volcano, which forms three-quarters of the island’s mass. Catch a lift to the top with your bike, then cruise down 21 switchbacks, passing through as many ecological zones as you would on a Canada-to-Mexico road trip. You can also golf the course that hosts the PGA Tour’s Tournament of Champions each January.

Hungry for culture? Hire a hula instructor for a lesson nearly anywhere on Maui. Shop the galleries of Paia, then strap in for the world-famous Road to Hana, a drive tracing the rugged black-lava coastline.

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Maui is also the access point for the Molokini atoll just off the coast, where visitors can snorkel an extinct volcanic caldera. But the caldera’s not your only option for gorgeous waters to explore: Get a mask and fins and then zip over to the beach town of Olowalu on the west coast where you’ll find a nursery for blacktip reef sharks, as well as a “cleaning station” for mantas and green sea turtles.

The uninterrupted three-mile stretch of Papohaku makes it one of the longest beaches in the state.

5. Molokaʻi

  • Nickname: The Friendly Isle
  • Highlights: Adventure, bird-watching, macadamias, national historical park, swimming, and snorkeling,

Molokaʻi packs in plenty of beauty, adventure, and also authenticity, thanks to the high percentage of Native Hawaiian descendants living there. Papohaku Beach, with three miles of silky white sand, fringes the island’s west end. The sunbathing and camping are superlative here, but avoid swimming in the dangerous breaks between October and March.

Don’t miss Kalaupapa National Historical Park, created to memorialize the leper colony that once existed here (some residents still live at the site, but they have been cured of leprosy). The classic Pali Trail leads down to it—switchbacking 3.5 miles down some of the world’s steepest sea cliffs—but a landslide in late December 2018 has closed it indefinitely.

Instead, visit by air (instructions and options are spelled out on the park service site) to experience this unique site, tour the settlement, and see the world’s tallest sea cliffs, the dramatic Kalaupapa Cliffs, rising dramatically from the Pacific.

6. Oʻahu

  • Nickname: The Gathering Place
  • Highlights: Big city, family friendly, fine dining, historical sites, luxury resorts, museums, national monument, nightlife, shopping, surfing, ukuleles, urban art

On Oʻahu, Honolulu is undergoing a renaissance of art, culture, and cuisine, with a foodie scene that fuses Pacific Rim flavors with Hawaiian regional cuisine. Enjoy the resort hot spots of Waikiki and Ko Olina, but make sure to venture beyond them. Pay your respects to local culture and history at the extensive Bishop Museum and at Pearl Harbor, now the World War II Valor in the Pacific National Monument.

Commission an instrument from Ukulele Hall-of-Famers or dip a smoked-beef brisket bánh mì in aromatic phở at Piggy Smalls, an outpost run by Andrew Le, a chef at the forefront of the efforts to include regional cuisine on Hawaiian menus. Or hit the North Shore, where 36 breaks grace the “Seven-Mile Miracle,” a storied stretch of surfing heaven.

Not quite ready to catch a world-class wave? Rest easy: Oʻahu has more mellow aquatic options with the lovely Lanikai Beach and the Hanauma Bay underwater park. Honolulu often has the best airfare deals, too, as the state’s main hub.

It’s difficult to go wrong with whatever island you choose to visit. The hard part comes when you have to leave Hawai’i to return home.

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