Anyone who knows me or has followed me recently knows that I love Hawaii. How much so? Well I’ve been to five of the Hawaiian islands. To some travelers, that may not be too big of a deal, but when you consider that my first trip to Hawaii was February a year ago, then that kind of makes it a thing. But what I love most about Hawaii isn’t the endless supply of mai tais (though I’ve yet to turn down a mai tai), nor is it the milk chocolate toffee macadamia nuts (but seriously, how good are they?), nor the POG juice (that’s not quite as good anywhere but in Hawaii). But rather it’s that every Hawaiian island offers a different type of trip. When I go to a new island in Hawaii, I know that while it may principally be the same place by traditional definitions, the experience will be far different than the last island I visited.

So today I highlight each of the Hawaii islands I’ve visited and what each one represents to me.

Lanai: The off-the-beaten-path island

On paper Lanai should be my favorite island. It has 3 main paved roads, 400 miles of unpaved roads, no stoplights, and one franchise. Now that’s island life as it should be. There wasn’t a single time that I went to one of the local beaches that I saw someone. Each time I visited a new solitary beach, I thought to myself, “What a great place to go skinny dipping?” (And don’t ask me if I did!) You don’t go here for nightlife. You don’t go here for the things to do. You go here to escape those things. You go with you and your boo for a place where time and life nearly stands still. And you go to have some of the best poke you’ll ever have at the Lana’i ‘Ohana Poke Market, which is open for a mere few hours per day. And maybe you go and do a little off-roading and skeet shooting (because that’s a thing here).

The island of Molokai from the Hawaii island of Lanai

The island of Molokai as seen from the Garden of the Gods on Lanai

Lanai Hiking trail

Hiking the rugged coastline of Lanai around Kaunolu Village

Polihua Beach on Lanai in Hawaii

One of many secluded beaches on Lanai, Polihua Beach

Oahu: The foodie island

Everything that Lanai is, Oahu is not. If you want city life, then this is the island you’ll find that on, as I often feel like I’m back in L.A. when walking the concrete jungle of Honolulu. My first day there found me doing something of a progressive lunch around Waikiki that resulted in a plate lunch (quintessential Hawaii lunch), macaroni salad, malasadas (the best doughnut you’ll ever have), and a shave ice (and don’t you dare call it “shaved” ice), all within a few blocks of one another. In general, I see Hawaii as one of the most underrated foodie destinations in the world, with Oahu really positioning itself as the best place to get the full experience of Hawaiian cuisine. Oahu even has its own foodie festival, the Hawaii Food and Wine Festival, which is celebrating its fourth year in August.

Hawaii flyover

Leonard's Bakery on Oahu in Waikiki

Your first and last stop in Waikiki, Leonard’s Bakery

Oahu - Malasadas

Maui: The all-in-one island

Maui without a shadow of a doubt is my favorite island because I see it as the one island that offers all of Hawaii in one place. Off-roading, check. Paragliding, check. Nightlife, check. Offbeat beaches, check. What I love about Maui is that to cater to such a wide-range of travelers, it can be experienced in its entirety on one trip as long as you give yourself a good five to ten days. With that said, I’ve split up my trip between the west end of Maui, which is the busier side of the island and the north side, which is where the famous Road to Hana begins. Why I find myself wanting to go back to Maui time and time again is its diversity in landscape and things to do, unlike some of the Hawaii islands that aren’t so versatile.

Maui Kahakuloa Head

Kahakuloa Head as seen from West Maui

Maui Hawaii paragliding

Maui snorkeling in hana

Sunrise Hana

Maui sunrise from Hana’s Travaasa Resort


Kauai: The movie-like island

Kauai is Hawaii’s oldest island and if it feels as if it’s the most movie-like island of Hawaii, that’s because it is, having taken center stage in movies that have included Raiders of the Lost Ark, Jurassic Park, King Kong, Six Days/Seven Nights, and Honeymoon in Vegas, just to name a few. You might as well also call it the “lover’s island” because it’s romantic as hell. Just ask the guy who went solo over Valentine’s Day weekend. But the landscape is so stark, reminding you why it’s been used in so many movies. Some highlights: Waimea Canyon (known as the Grand Canyon of the Pacific), numerous tropical gardens, and a plethora of dramatic waterfalls, such as Manawaiopuna Falls, which is often advertised as “Jurassic Park Falls.”

Kauai - Waimea Canyon

Kauai’s Waimea Canyon

Kauai waterfall

Hawaii, the Big Island: The nature calls island

Hawaii, the Big Island is something of an otherworldly island to me. One moment you could be dipping your toes into warm water on a black sand beach and the next you’re peering up at Mauna Kea with snow atop it. The top of Mauna Kea is also home to one of the most important observatory sites in the world. Not to mention the peak, at nearly 14,000 feet, features killer sunset views. How many times do you get to the see the sunset above the clouds? Oh, and did I mention there are several volcanos on the island? Hawaii, the Big Island, to this day is the only place I’ve ever seen molten lava. My favorite part of the island, however, is Waipio Valley, much of which isn’t accessible by car, featuring dramatic cliffs and a series of tall waterfalls.

Big Island Fly over

Big Island Waipio Valley

Hawaii, the Big Island’s Waipio Valley

Mauna kea sunset on Hawaii, the Big Island

Mauna Kea sunset on Hawaii, the Big Island

Read more of my destination content (including Hawaii) on the Expedia Viewfinder blog.