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A visual guide to choosing the perfect Hawaiian Island for your next visit.
By Eric Lindberg

Tropical, multicultural, and distant, Hawaii is like an overseas cousin we rarely see. We mostly understand the language (except for Hawaiian and pidgin), and the fast-food joints and big-box stores bear familiar American names. But drive five minutes from any island airport and it’s obvious by the landscape, architecture, and local attire that we’re far from Colorado.

Although each of the main islands is within sight of at least one other, each with its wet (windward) and dry (leeward) sides, they’re all vastly dissimilar in geological time. As a result, the newer islands look and feel different from the older ones.

So how do you choose which island to visit on your Hawaiian vacation? Here’s a visual guide based on a dozen years of travel to this remote archipelago.

KAUAI Navigating isolated beaches

The journey to Kauai is a geological leap back 4.5 million years in time to the oldest member of the island chain. Known as the Garden Island, Kauai is the embodiment of a tropical paradise: luxuriant and gentle. Over those millions of years weather and sea have eroded the sharp volcanic edges into a softer landscape. For me it’s a retreat, a place to recharge and rejuvenate while soaking in the sweetness of the island. I can choose from a variety of activities or I can do nothing; either option reveals the calming nature of Kauai. Even the traffic here is laid back, with people frequently slowing down to let other cars merge onto the road.

Kauai is the smallest of the four islands. The main road almost entirely circles the island, stopping only for a 15-mile gap along the rugged Napali Coast. Most of the interior is roadless and uninhabited, so exploring the island thoroughly requires more than a rental car. Deciding how to do that is part of the charm.

The quickest way to get oriented on Kauai is with a helicopter sightseeing tour. Starting from Lihue, flights zip up Waimea Canyon, the largest canyon in the Pacific, crossing rugged ridges and then dipping downward and following the Napali Coast, the most stunning coastline in all of Hawaii.

No other Hawaiian island has such isolated beaches as those tucked into this remote coast. They’re only accessible by a long paddle or hike, so most visitors view the shoreline from a catamaran cruise along the coast. There’s plenty to see even from the water: spinner dolphins, green turtles, waterfalls, and one of the most magnificent coastlines in the world.

With so many options to choose from, it’s hard for me to sit still and do nothing. As temped as I might be to go kayaking, body boarding, or hiking, Kauai remains for me a place to quietly recharge and rejuvenate. On each visit I indulge at Hanalei Day Spa, where a seaside massage and the soothing shush of waves pull me gently into island time. I may follow with a stroll at Kilauea Point Wildlife Refuge to watch the frigate birds, tropicbirds, boobies, and albatross. Or I might take a long walk along the beach at Hanalei Bay or Anini or Poipu. The healing energy of the island seeps into my body and I feel the magic of Kauai once again restore my spirit. Sometimes doing nothing is the best thing to do in Hawaii.

HAWAII Lava flows and star fields

Twice the size of the other islands combined, Hawaii Island is the newest member of the archipelago. Raw and volcanic, it’s still growing due to lava that spills from Kilauea and flows into the sea. Nature is the star attraction here, combining land, ocean, and sky in ways that no other island can offer. Locals say that the mana (spiritual energy) is strong on Hawaii because of the presence of still-live volcanoes. This is not a timid island. And that’s a plus for those with an adventurous streak.

Hawaii’s wet and dry sides are the most strikingly different of all the islands. Blame it on the five volcanoes that block rain clouds from drifting west. As a result, Hilo and the windward side are more humid and tropical with frequent rains. The Kona or leeward side lies in the shadow of those volcanoes, leaving that coastline drier and sunnier. Each side appeals for different reasons.

Hilo on the windward side is a vibrant blend of Asian, Pacific Island, and Hawaiian cultures. Clouds and rain are common here, and for many visitors a relief from the constant heat and sun of the leeward side. A walk through the daily Hilo Farmers Market is a window into the culinary community where over 200 vendors sell everything from fresh flowers and luscious tropical fruits to goat cheese, surfboards, and bento box lunches. Recognized as the best-preserved old-style Pacific town, Hilo is where America meets Asian Pacific culture, a contemporary Hawaii that feels far from the west coast resorts.

When the beach beckons, I head to the sun-drenched leeward side. Most of Hawaii’s resorts and beaches are here along the Kona and Kohala Coasts. Undeveloped, less-crowded sandy stretches lie at the end of dirt roads that meander through the lava fields. This coastline also offers the best snorkeling. What you won’t find on either side are plentiful surf breaks as found on the other islands.

Halfway between Hilo and the Kona Coast lies the island’s hotbed of volcanic activity. Stretching from sea level to 13,677 ft. Mauna Loa, Hawai’i Volcanoes National Park with its rainforests and volcanic landscapes is a crown jewel of the state. Expect the unexpected here: steam rising from hidden vents, rainbows arching into the ocean, rainfall while the sun is shining, and the vivid nighttime glow of erupting Halema’uma’u Crater.

“If you knew the stars, you could find your way.” Guide Taj Flora of Hawaii Forest & Trail is leading a tour 13,796 feet above sea level to Mauna Kea, one of the island’s stellar attractions. “The stars were what the ancient Hawaiians, and in fact all our ancestors, used to navigate and to anticipate the seasons.”

The drive up Mauna Kea to the summit for sunset followed by some of the best stargazing on the planet is an experience that can’t be found anywhere else in the islands. Peering through the free telescopes at the visitor information center below the summit, I’ve looked at Saturn’s rings, the craters of the moon, Venus, and Alpha Centari while standing under a night sky radiant with thousands of stars.

OAHU City life and surf culture

Oahu is for many visitors their first taste of the islands. With icons like Diamond Head, Waikiki, Pearl Harbor, and Banzai Pipeline, this is the birthplace of Hawaiian tourism. There’s vibrant nightlife here, something no other island can claim. It was at a Honolulu street food cart decades ago that I learned to use chopsticks, and these days a red-hot culinary scene ranges from gourmet food trucks to foodie destinations such as Chef Mavro where you will dine as well as anywhere on the planet.

I think of Oahu as a town and country island. On the urban side, Honolulu with its museums, restaurants, and entertainment radiates the cultural energy of a vibrant city. Touristy Waikiki has world-class people-watching and urban beach culture. The Bishop Museum is the world’s foremost museum of Polynesian history and science and a must for anyone wanting to learn about Hawaii’s people and past. And Pearl Harbor’s role in America’s history is ample reason to spend an afternoon or day here.

But the beauty of Oahu is that the natural world is never far away. On my last trip to Oahu, I left Waikiki early one morning and drove up the leeward side to Waianae Harbor, where I joined Wild Side Specialty Tours for a cruise in search of whales, dolphins, and turtles. When a large pod of spinner dolphins appeared, we pulled on masks and snorkels and spent 20 delightful minutes swimming with them. I was back in Waikiki in time for a surfing lesson that afternoon followed by a beachfront dinner.

For an extended country stay, I might check into one of the new resorts at Ko’Olinasuch as Marriott Ihilani and enjoy Hawaiian fusion cuisine at Roy’s. On the eastern coast I head for the beaches of Kaneohe Bay or further north to Turtle Bay Resort for a night or two at one of the island’s prettiest resort settings. Each winter the North Shore at the top of the island is the epicenter of Hawaiian surf culture and home to some of the world’s most famous surf breaks. Throughout the year the laid-back vibe here is worlds apart from the city energy of Honolulu. After a stroll around funky Haleiwa, an ocean swim, and a shave ice, I’m back in Waikiki for sunset and a mai tai.

Although Oahu is the most developed island, the urban pleasures of Honolulu and Waikiki far surpass those of all the other islands combined. When I’m ready for some quiet beach time, a 1-2 hour drive brings me to any of more than a dozen heavenly beaches upcountry. This town-and-country aspect is what sets the island apart from the rest of Hawaii. On Oahu you can have it both ways.

MAUI Jagged shores and jungle trails

Compared to Kauai and Hawaii, Maui’s coastlines are more developed. The hotels and condos along the drier coasts at Kihei/Wailea and Ka’anapali cater to visitors who enjoy relaxing along sunny beaches amid a resort atmosphere. Those beaches rival any in Hawaii.

But there’s a balance with nature here that appeals to many visitors. Massive Haleakala Volcano dominates the island, and upcountry along its slopes the cool air and rainfall create a perfect climate for anyone wanting a break from the coastal sun and sand. Continue upslope to Haleakala National Park where more than 30 miles of hiking trails in the summit area lead into a vast volcanic realm. Although less geologically active than Hawaii Volcanoes National Park, Haleakala is still stunning in its starkly dramatic landscapes dotted with rare silver sword plants found nowhere else in the world. Native Hawaiians believe that mana is very strong here along the rim of the volcano.

Each year between December and April Maui is the premier place in Hawaii to see humpback whales during their winter residence. Thousands of humpbacks come to shallow Auau Channel between Lahaina and Molokai for mating and calving, offering the chance for close encounters with these cetaceans.

Despite the development at Ka’anapali and Kihei/Wailea, snorkeling along these two coasts is among the best I’ve found in Hawaii. Encounters with green sea turtles are common. The diversity and quantity of fish and coral here can be astonishing. And in winter I often hear the mystical song of the humpback whale when I’m face down with mask and snorkel paddling around the reefs.

Another only-on-Maui attraction is the famed Road to Hana. This 52-mile winding drive passes through an Eden-like jungle of flowering trees, waterfalls, and infinite variations on the color green before reaching Hana on the east coast. The pace here is much quieter and often rainy, but the lush vegetation and a couple of nice beaches makes the drive worthwhile. Continue driving past Hana to the Seven Sacred Pools and bamboo forest of lower Haleakala National Park and you’ll feel far from home.

Hana is a world apart from the resorts of the south and west coasts. It’s in places like this, and the rim of Haleakala, and Auau Channel, where residents and visitors alike experience what’s been called the gentle, healing energy of Maui. Over the years many islands transplants have told me, “I didn’t choose Maui, Maui chose me.”With bamboo forests, volcanoes, and whales all in a day’s drive, it’s easy to see why people keep returning to the magic of Maui.

Which is my favorite? After countless trips here, I find that no one island outranks the rest. They’re all my favorites. In the end it all comes down to what I’m looking for in my island experience: relaxation, adventure, rejuvenation, or energizing culture.

And this is why I never tire of Hawaii and why I return year after year to this remote archipelago in the middle of the Pacific. There’s always something new to discover.

Eric Lindberg ( is a freelance writer and photographer based in Lakewood. He is the 2013 and 2011 Photographer of the Year, Society of American Travel Writers.