I had wanted to visit Hawaii since I was ten years old when I ravenously digested the novel Hawaii by James Michener. There was just some intangible quality about the way in which he brought to life the history and traditions of the islands that made me anxious to explore them. I wouldn’t get the chance for another 24 years when I eventually found myself in Hawaii for the first time. Even though I felt like I spent a lifetime preparing for the trip, there were still plenty of things I wish I had known before my first trip to Hawaii.
1. Every island is different
It’s easy for an outsider, especially one who has never before visited the Hawaiian islands, to paint them all with the same broad brush. They all are part of the same state, are pretty close to each other and should be about the same, right? Not only did I quickly learn about the natural differences between the islands, but I also noticed the cultural ones as well. There are six main Hawaiian islands which most tourists visit: Hawaii, Maui, Oahu, Lanai, Molokai and Kauai. A variety of influences have separated the islands by more than just water, and you really can’t say that you know Hawaii if you haven’t explored them all. I’ve only been to two: Oahu and Lanai, and of course the two couldn’t be more different. In spite of the differences though, I did notice a commonality, a common sense of belonging. While there are regional and local differences, I found incredible pride about living in Hawaii and for some, being considered Hawaiian.

2. Hawaiian shirts are ok
Everyone knows what a Hawaiian, or Aloha, shirt looks like. It’s those brightly colored, sometimes tacky loose fitting shirts that everyone seems to wear whenever they visit a tropical destination of any kind. In Hawaii though it’s much more, and the tradition of the Aloha shirt has become a part of everyday life. In the 1960s, the trade association for manufacturers of Hawaiian or aloha shirts, the Hawaiian Fashion Guild, started a movement to make aloha shirts accepted in the workplace. This resulted in a gradual loosening of the rules and aloha shirts began to slowly creep into the workplace.
Then in 1965, the Hawaiian Fashion Guild started to lobby for “Aloha Friday”, a day of the week when employers would allow their employees to wear aloha shirts. The idea was an instant success, particularly among younger workers, and by 1970 aloha shirts were fully accepted business attire for any day of the week.
Today you see people wearing this tropical shirt everywhere and for every occasion. I wish I had known that it was much more than a kitschy tourist tradition though or I would have brought a few more for my trip.
3. Food tradition
A few months ago I was watching cable news when I noticed a strange segment about Hawaiian food. It wasn’t strange necessarily because of the food, which honestly can be a bit odd at times, but because of the reactions of the reporters. I watched as they cast disapproving glances at spam and rice rolls and outright hatred when presented with loco moco.
Granted, I wasn’t fully awake, but I was genuinely surprised at the treatment Hawaiian cuisine received at the hands of these talking heads. It made me wonder how many people felt the same as these self-important blowhards and how those opinions might change if they understood the roots of these culinary oddities. No where else in the United States exemplifies the concept of a melting pot better than Hawaii. Over the centuries people from all over the world have immigrated there, bringing their unique culinary traditions with them. These traditions intermixed over time and the result is Hawaiian cuisine as we know it today. So don’t be afraid, order the spam, rice and eggs at breakfast and try loco moco at least once.
4. Tourists vs. residents – multiple layers
I’ve been to many tourist hotspots around the world and I thought I knew what to expect. Usually the destinations are cities, like Paris or Rome, and they blend the touristy with the local in a mix that works for everyone. During the day I join the other tourists for sightseeing and then at night I seek out the locals for their best dining recommendations. Hawaii was a little different for me though not because of this tourist/local dichotomy but because it’s everywhere. I don’t think I’ve visited another place where the entire region, or in this case state, was itself the entire travel destination. Unlike Florida or California, tourists can be found in every nook and cranny in Hawaii, hiding under rocks with their festive Aloha shirts. It took me a couple of days to realize this and it changed the way in which I sought out local experiences.
Instead of looking beyond the tourist sectors or neighborhoods, I had to look within them. A great example is in Honolulu, which all too often gets overlooked by travelers. One afternoon I decided to explore the historic Chinatown neighborhood, a tourist destination in its own right. But it is so much more than that, it is a living, active community that buzzes with a life of its own. Here tourists weren’t the focus, we were a bit of an annoyance as the people who live there went about their daily lives. It was a great way to escape the neon lights of Waikiki and get to know the city a little bit better.
5. Hawaii stays with you
I’ve been fortunate in my life. I’ve visited some pretty amazing places around the world and engaged in what many would call once in a lifetime experiences many times. While I’ve enjoyed just about every place I’ve been, most of them haven’t really captured me, they haven’t stuck with me in the same way Hawaii has. I’m not alone, just about everyone I ask says the same thing. No one expects to have a bad time in Hawaii, it is paradise after all, but most people don’t expect the infectious desire to return that Hawaii instills in many of us. Honestly, I expected my first trip to Hawaii to be my last for a while. It’s far away and there are so many other places to see around the world. Within six months of my first trip I was back, recalled through some unknown force and I’m always looking for some way, anyway, to return to these islands and learn as much about them as I possibly can.
Many people think they know what to expect from Hawaii, but few get it right the first time. What surprised you about your first trip to Hawaii?




Who am I? I am a typical Gen-Xer and recovering cubicle-dweller who has a passion for all things travel. My site brings a unique perspective that is hard to find online. I am not a backpacker, nor am I...





I so agree with you on that last point. We went to Oahu for our anniversary in March, and while I expected to have a nice time – beach, great hotel, celebrating with my husband, what’s not to like – I never thought that I’d feel such a desire to go back as soon as possible. There’s something about it!
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I don’t know that anything surprised me on my first trip to Hawaii, I was just so glad to be there! Wait I just remembered something! I remember it pouring down rain all night the first night and thinking I didn’t come here for it to rain! Woke up in the morning to absolutely beautiful weather. It rained every night and was beautiful every day!
When I visited the island of Hawaii I was very surprised because it didn’t look like the “normal” Hawaiian islands I had visited before. I wasn’t ready for the lava rocks on the Kona side! Such a very diverse landscape it is amazing!
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Hello Matt,
I’m a senior citizen who reads you everyday. Glad to hear you liked Oahu and Lanai, but you missed a great opportunity in not visiting Maui. There is something magical about Maui that you should experience. I am a 40 year transplant to Maui and visited many parts of the world, and see that everytime. I’ve visited every island in Hawaii, including Niihau, the “forbidden” one, and Maui is “no ka oi” …can’t be beat.
You also would want to visit the volcano on the Big Island. Where in the world can you walk over harden lava with lava flowing 20 feet away. Where in the world can you see lava flowing into the ocean. It is an unreal experience. Keep up the good work!
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Matt Long Reply:
August 18th, 2011 at 5:53 pm
Hey there Bernice and thanks for reading! I’d LOVE to visit those places, I just haven’t had the opportunity yet. But I hope to visit soon!
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Going back to Maui, next week and I was most surprised by how many outdoor activities I could enjoy and how “un-touristy” Maui could be. I didn’t really want to go the first time. I thought, “If I’m going to the South Pacific, I want to go to Fiji or some out-of-the-way island.” I’m used to Disney World and am over the “tourist” destinations. Maui was SO much more than that and can’t wait to get back.
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Nicely done.
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I can’t believe you ravenously digested Michener. Great post to read prior to a trip to Hawaii, hopefully I’ll get there soon.
stay adventurous, Craig
ps – great shirt.
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Matt,
Loved this article on Lanai, Hawaii.
We’ve been to Oahu and the Big Island and like Tim said I was blown away by how ‘Incredibly Un-touristy’ the Big Island was!
We found beautiful white sand beaches that were completely deserted and a amazing beach that had Green Sand!
My son learned how to surf and I’m looking forward to SUPing on our next trip.
But, like you said. Hawaii Captured us, too. I can’t wait to go back and I’m so happy that some of our family have decided to go to school on Oahu and retire on the Big Island.
Mahalo
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Aloha! Glad I’m not the only one that can’t seem to shake Hawaii. Lived there for 5 years before moving to Hong Kong and miss it every day. I guess my favorite surprise was that it can rain when the sun is shining. They call it liquid sunshine. And I miss never having to wear shoes. Rubber slippers are Ok just about anywhere. Do try to get to Big Island is you haven’t already and hike across the bottom of the craters. It’s unlike any place you’ll ever see.
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I first came to Hawaii with my 2 sons and a double stroller. I stayed for 3 years. After they both graduated high school I decided to return. To my surprise my younger son switched to UH. After his culture shock, we’d moved to Atlanta when he was almost 5, and his transfer to a school outside of Savannah – I contemplated returning also. I’m able to go home every 4 to 5 months for a couple of weeks but the draw back to Hawaii is undeniable. I’m just at peace here. I look at all of the movies that I used to watch just to see Hawaii after moving to Atlanta and now my eyes well up from knowing i’m back instead of crying from yearning. But bro Iz’s “over the rainbow” still makes me cry. I don’t understand the draw Hawaii has on so many but I seem to prosper here like no other place.
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