I recently saw this article by Travel + Leisure ranking the Hawaiian islands according to T+L readers. Like anything that pertains to Hawaii, my favorite place in the world, I’m naturally curious so I dug in. I was happy to see the Island of Hawaii as #1 as it too is my favorite.
When someone learns we have lived in Hawaii previously they will ask “where should I go?” And man, you would not believe how seriously tough that question is. The Hawaiian islands are so unique that it makes it difficult to answer that question without a serious inquisition about who you are, how you are, what you like, and what you envision for your trip to Hawaii.
The love of an island is so subjective and it really is just a matter of perspective. While many people I’ve spoken to who have visited will claim Maui as their favorite, it is my least favorite. The T+L article only covers the five main islands so I’ll do the same in this article.
Let’s dive in and get to the heart of my opinions.
- Island of Hawaii – The Big Island
Hands down my favorite. The island is so big and offers so many incredible experiences. It is also the only island that has an active volcano and how many times are you going to be on vacation and get to see that kind of action? One of my fondest memories of our time in Hawaii was the tide pools we randomly stumbled upon. Tide pools are perfect for little kids and our boys were at the ripe age to enjoy splashing around in the pools shaped by lava rock. It was amazingly picturesque. We also had the crazy adventure of driving the southern shore and visiting the green sand beach and black sand beach. Two seriously unique beaches of Hawaii. While not your stereotypical sit back and relax with a mai tai in your hand, well worth a visit. Getting to the green sand beach is not for the faint of heart, nor for everyone so it goes back to the probing questions about who is the audience. The Big Island is certainly worthy of its own BIG post.
Green Sand Beach, The Island of Hawaii 
Magical Tide Pools, The Island of Hawaii
- Kauai
Kauai serves up the old-school authentic Hawaii vibes. There isn’t a ton of development there and it is so green and lush. As members of the military, we had the unique pleasure of being able to stay at Barking Sands on the western side of the island on a Navy base in Kekaha, Hawaii. This area is unbelievably remote. Just being able to walk out onto your own semi-private beach to watch the sunset over Niihau night after night is amazing. If you are a member of the military I’d definitely make this a must-do life experience. The location is also great for accessing Waimea Canyon, the Grand Canyon of the Pacific.
If there is an island that I’d say a helicopter tour is a must-do it is Kauai. Being able to see Waimea Canyon and the Napali Coast from the air is magical.
- Oahu
I have to say I am partial to Oahu as that is where we lived. I’ve literally hiked miles over that island, seeing areas so unbelievably magical and only accessible when you get out there and walk it. Some of the best hikes aren’t the ones traditionally visited and that is fine to keep the trails well maintained and saved for those in the know.
It is also home to “our beach,” and the beach that has forever ruined us to any other beach in the world: Lanikai. From where we lived in Kailua it was an easy bike ride to dip in the turquoise and calm waters with a beautiful view of the Mokes. I’m having a Calgon take me away moment just thinking about it.
4. Lanai
Full disclosure, at this point I’ve never officially stepped foot on Lanai, but I have dove the waters directly off of the island giving me a great vantage point of the topography and one of two main resorts on the island. If you are into hunting, I believe this is your island to visit. If you are looking for ultimate seclusion and a complete resort experience, this is your island. There is also some pretty spectacular diving right off the island. I dove the cathedrals, which are lava shoots and caverns where rocks have fallen from the ceiling allowing sun rays to shine through the crystal clear water creating a church-like experience.
5. Maui
I feel like I really have to explain myself with this one. It isn’t that Maui isn’t spectacular, it is just to me, most like the mainland. I think the reason so many tourists love it is because they feel comfortable there, and they are supposed to, because I feel like that is what it has been developed to do. It is super tourist-friendly. It is also home to my all-time favorite luau. The gold standard luau by which all other luaus are judged.
My favorite memory spot in Maui is (shocker, another beach) red sand beach. You’ll see this spot mentioned on some guides on the Road to Hana. When I visited it was late in the day and there were a total of six of us on the beach. Again, not your stereotypical chill beach experience but very unique and picturesque.
Molokai isn’t a traditional stop in the tourist circuit but I had plans to visit after reading Moloka’i and Daughter of Moloka’i by Alan Brennert. The trip was to be a historical look at the island and Kalaupapa. But alas, COVID. So the trip never happened before we moved. Still just another super interesting aspect of Hawaiian history.
There really is so much to love about all of the Hawaiian islands and if you get me at a cocktail party I can go on and on about all the magical places, but if you ask – just be prepared for an inquisition before I answer what island you should visit.
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