You’ve decided it’s time to cross “Vacation in Hawaii” off your bucket list and book a trip, but you’ve never been before and are not sure which island to try. Your friends have serious opinions about their favorites, but all agree on one point: With Hawaii you really cannot go wrong.

The 50th state to join the union, Hawaii is a string of 136 islands, only seven of which are inhabited by humans, with only six that are travel destinations.

Each of these (Lanai, Molokai, Kauai, Oahu, Maui and Hawaii) has a distinct personality, history, and topography with unique activities and amenities to recommend it. So what are the differences between the Hawaiian Islands and how do you possibly choose which one to visit?

Are you looking to scale a volcano? Buzz a waterfall in a helicopter? Or explore World War II history? Maybe you’d like to sip a Blue Hawaii cocktail in the very bar where it was created or dance the hula in the town where it was born. Are you in search of peace at the most deserted beach you can find or do you just want to get your high-end shopping on? Let’s consider the options:

Comparing the Hawaiian Islands


A hidden gem, the smallest and least-visited island is the apostrophe-shaped Lanai. If you are eager to get off the grid and enjoy some alone time, this is your haven. You will likely see more cats, fish and birds than you will people. Lanai has no traffic lights, no public transportation and no discernable nightlife. Nicknamed “the Pineapple Isle,” it was once home to a plantation that produced 75% of the world’s pineapples. Today it is owned almost entirely by Oracle Founder Larry Ellison, who has been careful to preserve tiny Lanai’s off-the-beaten-path charm.

Lanai is ringed by empty golden beaches with aqua-blue waters teeming with fish, playful spinner dolphins and humpback whales that breach offshore in winter. Hulopoe Bay at the foot of the Four Seasons Resort is a protected marine preserve with tidepools and ideal snorkeling conditions. Lanai is beloved for its quick ferry to Maui, world-class golf courses, sunset boat cruises, fishing, the Garden of the Gods, archery, horseback riding and fine dining. And be prepared to enjoy a lot of pineapple.


Often called “the Friendly Isle,” Molokai is known for its warm spirit and slow pace. “Aloha” is not just a word here, it’s a lifestyle. You can still find old Hawaii here — the Hawaii of 50 years ago — preserved in time. More native Hawaiians live here than on any other island.

With its rich cultural history, awe-inspiring natural beauty, the tallest sea cliffs in the world, massive volcanoes, rain forests and silky white-sand beaches, Molokai is a vacationer’s dream. You’ll see no traffic lights here either and no building taller than a palm tree. Once a leper colony, the stunning Kalaupapa Peninsula is often considered the prettiest place in all of Hawaii. Revel in abundant snorkeling, diving, surfing, fishing, whale watching, bird watching, golfing and hiking. As the birthplace of the hula, the dance is celebrated regularly, so bring your grass skirt.


“The Garden Isle” is aptly named for its unbelievably lush and pristine natural splendor. The oldest of the islands by millions of years, Kauai is home to one of the wettest spots on earth: Mount Waialeale that averages 450 inches of rain annually, creating an interior that is dense, misty and mysterious. It’s no wonder Jurassic Park filmed many of its scenes here. Add in the red-rock splendor of Waimea Canyon —“the Grand Canyon of the Pacific”— and the spectacular Napali Coastline with its soaring emerald green cliffs (accessible only by foot, boat or helicopter) and you begin to understand just how unforgettable this island is. Load your dictionary app because you’re going to run out of adjectives. Waterfalls grace all corners, Hanalei Bay inspires awe and the only navigable river in Hawaii awaits you. There is no end to the activities: kayaking, hiking, tubing, helicopter tours, surfing, diving and the largest zipline in Hawaii. Oh, and take a bow, South Shore: Sunny Poipu was once called the “Best Beach in America” by the Travel Channel and local Koloa Landing Resort was just crowned 2020’s “Best Pool in America” by USA Today. You can’t get out here fast enough.


Known as the “Gathering Place”, for its spirit of ohana, Oahu is an exciting blend of big-city amenities and artistic culture surrounded by gorgeous tropical scenery. Home to Hawaii’s capital city of Honolulu — and the majority of the state’s population — Oahu is an entertainment mecca with a vibrant restaurant and shopping scene. You’ll enjoy some of the finest dining in the state here and Japanese boutiques you won’t find anywhere on the mainland. Hit the town at night, and in the morning head to the world-famous North Shore to surf. Go parasailing over Waikiki Beach or swim with turtles in the many brilliant snorkeling waters. American history is on display at the Pearl Harbor museum and other poignant World War II memorials, and if you’re in the market for a handcrafted ukulele they don’t get much more authentic than here on Oahu.

By far the most popular destination among tourists, Oahu attracts nearly twice as many visitors as Maui annually. This happy place is a great choice for families — though your kids may never want to leave.


The “Valley Isle” of Maui is a tropical playground created by two merging volcanoes. Towering at 10,000 feet, Maui’s Haleakala is the largest dormant volcano in the world, creating 75% of the island’s mass. Its valley is 21 miles wide and 4,000 feet deep, large enough to hold the entire island of Manhattan. Catch a ride to the top then bike back down, passing through more ecological zones than seems possible.

Home to 120 miles of gorgeous coastline you will find white-, golden-, black-, or red-sand beaches. By law, no one can own a beach on Maui or has the right to keep people off of it (including resorts) so beachcombing is a way of life here. Tour the only working pineapple plantation in the country, go windsurfing at Ho’okipa Beach and scuba dive in the crescent-shaped Molokini Crater. Maui’s Olowalu Reef is a haven for manta rays and sea turtles. If you brave the harrowing Road to Hana drive up the black-lava coast — crossing some 54 bridges — be sure to stop often to witness stunning waterfalls and hidden beaches along the way. Maui is a great place to get lost — and to lose yourself.


The “Big Island” of Hawaii is the youngest and the largest of all — and it is still growing! More than 600 acres have been added since the Kilauea volcano erupted in 1983. When comparing the Hawaiian Islands this grandaddy is actually bigger than all the others combined! One of earth’s most ecologically diverse locales with 8 of the 13 different climate zones that exist in the world, you’ll find lush rainforest valleys, waterfalls, lava deserts and even snowy mountaintops. Sea mountain Mauna Kea is 4500 feet taller than Mount Everest and nature lovers will be wowed that 90% of Hawaii’s flora and fauna is endemic.

The Big island’s coastline stretches a whopping 266 miles and features beaches in an array of sand colors from powdery-white, jet black, and even some with green sand from ancient volcanic rock. The coast’s coral reefs are rife with fish, sea turtles and eels. Here on the Big Island you can go hiking in search of red-hot lava, bathe under a thundering waterfall, read your book on a massive white-sand beach as whales breach off the coast and wander the quaint villages for handmade art. The Big Island delivers big time.

The differences between the Hawaiian islands are vast, but one thing is for certain, no matter which one you choose to visit you will find adventure and beauty at every turn. In fact, sometimes the amenities you hadn’t even anticipated turn out to be your favorites!

If you’d like more information about any of the islands or are ready to make a reservation, please reach out to us at Koloa Landing Resort or by calling 808-240-6600. Aloha!

by Erica Karlin, Koloa Landing Resort