Though Hawaii remains an ever-popular destination for travelers, the 50th state is especially appealing at the moment, as it is easily accessible for both U.S. and Canadian travelers looking to book a last-minute trip. Vaccinated American travelers can arrive in Hawaii and travel between islands without quarantining. But which Hawaiian island to visit once you arrive? Though the idea of Hawaii has a powerful hold on the cultural imagination—swaying palm trees, swaying hula dancers, idyllic beaches, tropical luaus, big wave surfers, and more—far less is known of the vast differences between the islands. There are 137 islands in the Hawaiian archipelago, and are six major inhabited islands: Maui, Lanai, Molokai, Kauai, the Island of Hawaii, and Oahu. And the choice of which island to visit between all six is not so simple.
When booking a last-minute vacation, it’s important to consider which island is best for your needs—whether you’re interested in relaxation or adventure, nightlife or culture immersion. From the busy city streets of Oahu to the sophisticated luxury of Maui, the remote paradise of Molokai, and the pristine gardens of Kauai, where you stay in Hawaii hugely impacts your vacation experience. So, when booking a trip to Hawaii, before asking: “Which resort?” you should ask “Which island?” instead. And we’re here to show you how to do just that. Read on for your ultimate guide to the Hawaiian islands to decide which vacation is best for you.
Oahu
Nightlife Aficionados
(Image provided by the Hawaii Tourism Authority)
Home to the bustling Hawaiian capital of Honolulu, Oahu is perfect for travelers interested in experiencing the island culture (and local flavors, i.e. mai tais) long after the sun has finally set on the Pacific. (Hawaiian sunsets are vividly picturesque and gloriously protracted—at least, it feels that way when you’re on an island with an undisrupted view of the horizon.) While other islands tend to be quite a bit sleepier in the evenings (Lanai and Kauai, especially), Oahu and Maui offer the most after-hours diversions for the nocturnal nomad—and Honolulu is undoubtedly the nightlife hotspot. The capital city is teeming with beachside bars, late-night restaurants, local art galleries, and live music. If you’re the type of traveler who is eager to leave the luxurious confines of your all-inclusive resort, then Oahu is the island for you.
(Image provided by the Hawaii Tourism Authority)
There’s an array of options available for last-minute hotel deals in Honolulu—we recommend the Waikiki Beachcomber by Outrigger, which is steps away from the famous Waikiki Beach and features artwork by local artists, including world-renowned surf photographer (and Oahu native), Zak Noyle. Speaking of Hawaii’s native sport, visitors would be remiss not to take a surf lesson at the aforementioned Waikiki Beach—the waves along this famous shoreline were once the dominion of Hawaiian kings and queens. Or, if you’re feeling more adventurous, try your luck along Oahu’s famous North Shore. Finally, though Hawaii isn’t geographically close to any particular landmass—it’s the most remote island chain in the world—Oahu is the most accessible of all the islands for overseas travelers. The Daniel K. Inouye International Airport in Honolulu is the hub for all major airlines—and, as always, last-minute flights abound.
(Image provided by Zak Noyles)
Lanai
Wellness Warriors
(Image provided by the Hawaii Tourism Authority)
The smallest of the six major Hawaiian islands, Lanai is also one of the least-visited—only the island of Molokai, which doesn’t court tourism, has fewer visitors. Once a pineapple plantation, tourism to the island of Lanai only experienced an uptick quite recently, as it became home to two 5-Star resorts in Lanai City: Sensei Lanai, and the Four Seasons Lanai. Lanai offers travelers an opportunity to go off-the-beaten-path, and the remote island is particularly suited for honeymooners and/or wellness-seekers. (Not that the two categories are very dissimilar—isn’t the first rule of romance to love yourself first?)
(Image provided by the Hawaii Tourism Authority)
The private island, owned by Larry Ellison, also specifically attracts (and caters to) a luxury clientele. But, unlike Maui—also known as the “Beverly Hills” of the Hawaiian islands—Lanai is significantly more secluded. And a trip to the Four Seasons Lanai is incomplete without a sunrise hike to Pu’u Pehe, the 80-foot “Sweetheart Rock” rising above Hulopoe Bay. In nearby Manele Bay, the adults-only Sensei Lanai markets itself as a ‘luxury well-being resort’—and, in a year when mental well-being seems to be at a pandemic-induced all-time low—it’s a treat to discover that last-minute all-inclusive hotel packages are available for the weary traveler. Tranquility now, please.
Island of Hawaii
Adventure Seekers
(Image provided by the Hawaii Tourism Authority)
The Island of Hawaii is known as the “Big Island” because, at 4,028 sq. miles, it is almost twice the size of all the other islands put together.) Despite being the biggest, the Big Island is also the youngest—a mere 800,000 years old, to be exact. The Big Island is perfect for adrenalized explorers looking to immerse themselves in the tropical landscape. And the landscape on the Big Island is quite varied—Hilo, on the eastern side of the island, is a lush rainforest landscape (130 inches of rain annually), while on the western side of the island, the Kohala coast, it’s an “eternal springtime” with warm sunshine year-round (it rains less than 10 inches per year). Crossing the island, adventurers can explore the fern forests of Puna (just south of Hilo), and the lava plains of Kona to the west.
(Image provided by the Hawaii Tourism Authority)
Due to the diverse landscape and size of the island, we recommend renting a car to explore. Adventurers will surely be satisfied with a visit to Mauna Kea—also known as the tallest sea mountain on the planet (13,796-feet, or 4,205-meters, above sea level.) If you count the mountain’s height from the ocean floor—an additional 32,000-feet, or nearly 10,000-meters—then Mauna Kea is taller than Mount Everest. (But who’s counting?) Additionally, Mauna Loa, which covers half the island, is the largest active volcano in the world. But the most famous volcano in Hawaii is Kilauea, fittingly the home of the Hawaiian volcano goddess Pele, in Hawaii Volcanoes National Park. The volcano has erupted continuously since 1983, with the most recent eruption occurring in December 2020. We suggest an ATV tour of the national park to best explore the lava fields—how often do you get the chance to off-road amongst the ashes of an active volcano?
Kauai
Eco-Explorers
(Image provided by the Hawaii Tourism Authority)
It shouldn’t come as a major surprise that—of all the beautiful landscapes across the Hawaiian islands—we would select Kauai as the must-visit destination for nature lovers. (It is known as the “Garden Isle,” after all.) The oldest and northernmost island in Hawaii, Kauai is home to jagged green cliffs, serene coasts, lush rainforests, and rolling hillsides of hibiscus and Mokihana (the island’s designated flower.) Best of all? 97% of the island is preserved. To visit Kauai is to visit a pristine paradise, seemingly untouched by the clutter and congestion of modern life—and this concept of a land before time is quite fitting, as Jurassic Park was filmed on the island. We suggest signing up for Kauai ATV Tours to explore the wild environs—from hidden waterfalls to limestone caves. (And bring a change of clothing, as mud is inevitable.)
(Image provided by the Hawaii Tourism Authority)
Similar to the Big Island, there’s no shortage of outdoor adventures for the active traveler to immerse themselves in nature—from catamaran cruises and helicopter rides to the Na Pali Coast to ziplining above the tropical treetops of the rainforests in Koloa. And, although you needn’t be an adrenaline junkie to appreciate the island’s wild beauty, it is helpful if you have wheels. (Kauai is another island where we suggest booking a rental car.) Some of the best sights and sounds—and rainbows (!)—can be observed from the dirt roads of Waimea Canyon or beneath the eucalyptus canopy of the Tree Tunnel on Maliuhi Road. But whether you’re headed for the northern coast of Hanalei Bay or the southern shores of Poipu Beach, the landscape everywhere is magnificent. Into the wild, indeed.
Maui
Luxury Lovers
(Image provided by the Hawaii Tourism Authority)
If it’s luxury you’re looking for, then look no further than the island of Maui—the South Shore, to be exact, and the town of Wailea, to be precise. Wailea is home to a dazzling array of luxury resorts (the Four Seasons Resort Maui at Wailea is a perennial favorite), and—for savvy travelers—last-minute bookings can be attained by monitoring hotel deals and flights. Maui combines the 5-Star hospitality found on the island of Lanai with the bustling restaurant scene present in the capital of Oahu. Though, of course, Maui is certainly less busy than Honolulu, which locals describe as “the New York City of Hawaii”—albeit without the sleet, snow, or polar vortexes known to plague the Eastern Seaboard.
(Image provided by the Hawaii Tourism Authority)
But even if you’re not staying in Wailea, there’s no shortage of beauty to be found on the Hawaiian archipelago’s scenic “Valley Isle.” The Road to Hana is widely considered to be one of the most scenic routes in America, and we recommend allocating an entire day to said adventure. (And to drive carefully on the winding island roads.) The lookout at Iao Valley State Park is simply breathtaking, with jagged green mountains dramatic enough to rival Kauai’s Na Pali coast. In fact, there’s a bit of every island present in Maui, which is perhaps why it’s so consistently in demand as a tourist destination. Simply put: The island is popular for a reason. Finally, visitors would be remiss not to go searching for humpbacks during their trip, as Maui is the whale-watching capital of Hawaii. The Pacific Whale Foundation maintains a headquarters on the island and offers sailing excursions for guests—an activity that’s simply not to be missed.
Molokai
Culture Vultures
(Image provided by the Hawaii Tourism Authority)
Molokai is known as “the last Hawaiian place,” and the island doesn’t seek out tourism in the same way as the other islands in the archipelago—and this is deliberate. At 10 miles wide and 38 miles long, Molokai is home to far more native Hawaiians than visiting tourists. The Molokai tourism industry would rather foster a specific type of traveler (curious, respectful, engaged) than a vast quantity of tourists. And, as a result, if you’re looking for culture, beauty, and an off-the-grid Hawaiian experience, then Molokai is your dream destination. Be sure to watch the sunset at Kapalua Bay, or hike Kalaupapa—the highest sea cliffs on the planet (3,000 feet above the Pacific.) Explore one of the oldest royal groves in Hawaii: Kapuaiwa Coconut Grove, which was planted by King Kamehameha V in 1816. (We recommend visiting at dusk when the sky casts the palms in a pink glow.)
The Verdict
(Image provided by the Hawaii Tourism Authority)
Now that we’ve covered every island, there’s only one last question to answer: What should you do if you identify as more than one type of traveler? (After all, there’s certainly no rule that nightlife lovers and adventure seekers are mutually exclusive.) And if you’re interested in experiencing a combination of each vacation—luxury and nature, or culture and nightlife—well, you’re in luck. Vaccinated U.S. visitors can travel to multiple islands during their stay—no quarantine necessary. (Just be sure to consult the Hawaiian travel requirements prior to boarding your flight, of course.) And last-minute deals to Hawaii are easily found. Perhaps a romantic retreat in Lanai followed by a surf weekend in Oahu should be added to the agenda? After all, if it’s going to take 11 hours to get there—the flight time from NYC to Honolulu—you may as well make the most of your trip. Happy travels!
