Five Things I Wish I Knew Before Visiting Hawaii

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.

Downtown Lanai City

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.

Waikiki, Hawaii

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.

Diamond Head Sunrise

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?

By: Matt Long

Matt has a true passion for travel. As someone who has a bad case of the travel bug, Matt travels the world in order to share tips on where to go, what to see and how to experience the best the world has to offer.

48 thoughts on “Five Things I Wish I Knew Before Visiting Hawaii”

  1. 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!

      1. Melissa Andrews

        I totally agree. My husband took me to Hawaii in May of 2014. I fell in love. There are so many things to do. We hardly spent anytime in the hotel. I loved it so much, that in about 15 days i have the opportunity to take two of my daughters to Hawaii for the first time. Can’t wait…..ALOHA

    1. margaret mcquillan

      If you went in 2014 you will be most upset on returning. We have just returned 2020 Feb and found it so changed. All upmarket stores in waikiki itself ,great food but old type markets gone . Footpaths are dangerous when wet and very uneven they look nice . Stay away from waikiki and just see the island and visit waikiki for the day. Plenty of other shopping.

  2. 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!

  3. 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!

    1. 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!

      1. Hi Matt,
        Hi everyone. I liked what Matt wrote. I am moving to Molokai for a minimum of 6 months starting June 2016. I began this site because I could not find information on making money while you travel with a nurse. Molokai will be a challenge for employment. If anyone has pointers, I would greatly appreciate them. traveling with a travel nurse dot com.


  4. 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.

  5. 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.

  6. 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.


  7. 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.

  8. 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.

  9. i love hawaii, but ive only been to oahu, hubby born and raised in kailua, oahu. hope to move there soon. loved the post

  10. Hawaii not only sticks with you but becomes part of you. If this is not the best, most diverse, fun, interesting, loving etc etc place on the planet or I will go HE. I have encouraged my kids to seek a scholariship at UH. As a part of the pacific rim, my children realise that the potential in is endless. Fortunately they are really good at sport and are very very clued up. Life in Hawaii IS THE BEST.

  11. Hey TB, I have planted the same seed with my kids, and I live in Australia. I think I may have been a Hawaiian in a past life, can’t get enough of the place. Not only do you get a taste of mainland USA but you also get a big slice of the South Pacific. Maui is my favourite, proposed to my wife there and 12 years later took our kids there. Have been to the four main islands and would love to see the other two but would absolutely live in Maui if it were possible. Maybe when my kids both get scholarships at UH my wife and I will buy a nice little beach shack just out of Lahaina.

  12. I just returned from 8 days on the Big Island with my family. This was my 4th trip in 9 years there for me and my husband; the 2nd trip in 3 years for my kids. We average a trip every 3 years, so I totally understand what you mean by the “infectious desire to return.” After our first trip to Oahu and Maui in 2005, we knew we had to go back. We both got airline mileage cards to rack up the miles for future trips since tickets from the East Coast are so pricey. Europe used to be our go-to big trip, however, once we found Hawaii, nothing else seems worth it (although we did HAVE TO take them to Italy last year just to get that experience). We’ve been to Maui twice, Oahu, Kauai and the Big Island. I think my favorite island is Maui.
    The things that surprised me:
    1. The amount of vowels and apostrophies that can fit in some Hawaiian words.
    2. The difference in weather within just a few miles on every island.
    3. How untamed (and potentially dangerous) and untouched some places are, particularly on the Road to Hana.
    4. How everybody has a facinating story of how they came to live there (if they weren’t born there).
    My kids now have the same love of Hawaii. They’ll be heading off to college within the next few years. I could easily see myself retiring there (once those college bills are paid)!

  13. Loved reading all the comments here. I just returned from 2 weeks in Oahu and gorgeous Maui.It was my 4th visit, and each time the desire to return becomes stronger. Like fellow Aussie TFB, I also feel I must have been Hawaiian in a past life :).. Such is the pull of the place. I have wonderful memories of all my visits, and the list of things I want to see and do, gets longer each time.I first visited in 1977, and whilst many things have changed, the genuine spirit of aloha remains the same. Fortunately it is infectious and stays with you wherever you live.
    Maholo for a great post.. It’s encouraging to see there are others with the same Hawaiian addiction! ( and if TFB ever gets his beach shack near Lahaina, I’m there!! :))

  14. I completely agree with you! My husband and I went last March for our anniversary and I just booked a second trip to Oahu today! Only 125 days and counting! I honestly didn’t think I’d be dying to get back as quickly as I though, but the island is so relaxing. One of the best trips I’ve ever taken, and I’m sure this next trip will be even better!

  15. Not to rain on anybody’s parade, but Hawaii is not in the south pacific. Carry on…..

  16. I’m 72, our son has booked a vacation for our 50th Wedding Anniversary, we leave in a week, staying 5 days. I have back problems, just got Lasik Surgery, Dental work, and using a walking cane to get around. My Doctors have gave me the go, but I’m concerned that I will hold everyone back from having a good time. I have been all over Europe, however never been to Hawaii, or any of the Pacific Island, always wanted to go, I would stay if I had financial means to do so. If anyone has any advise for me, I would appreciate considering. I’m going, so don’t advise me to not go. :-).

  17. Lion Lekha Sharma

    I’am lucky to have read about the 5 points to remember before visiting Hawaii. I will be visiting Honolulu on 22nd June till 1st July for our Lions International convention from 26th to 30th. I will follow your recommendation and give my feed back.

  18. We just got back from Waikiki and the big island. We stayed in a house on the beach away from the tourists areas. It was about a hour from Hilo. We were treated like a local while we were there. Invited to parties and community functions. By the time we left, my children were calling people “Auntie and Uncle”. It was paradise.

  19. Thank you a lot for the article! Actually, I am going to move to Hawaii and I am trying to learn a lot about this destination. I am extremely excited and hope that I am going to be happy there!

  20. Great article! I just moved to Kauai in June 2015 and am seeing things from a whole other perspective. I came embracing everything different and I’m doing my best to try the foods, enjoy the culture ,and simply enjoy all that Hawaii has to offer. I am also blogging about my experiences in moving to Hawaii and found your blog when searching information on what people think about when they think about Hawaii. Thanks for your perspective! Blessings,

  21. Mahalo for writing a post that didn’t bash Aloha shirts. Whether you live on the islands, or your just visiting, wearing them is all part of the tropical experience.

  22. My husband was born and raised in Hawaii. His parents have since passed and as the executor of their will we need to return this spring to sell some undeveloped property. My husband has such fond memories of his childhood on Oahu. Could I ask what you all would recommend we do and see on Oahu? We’re not real touristy types. We’ve had a real tough year and tranquility sure sounds nice.

  23. Me and hubby and another couple is taking our first trip to hawaii and was wondering if maui or the big island would be a great first trip

  24. I have only been to Oahu but loved the laid back life style and how green the north side is. Will definitely be returning. Great article.

  25. I am heading to Maui, from Ohio, in 24 hours. I already don’t want to leave Hawaii.

  26. This is a great article. It makes me want to go to Hawaii, which was never very high on my list. Wasn’t against it just wasn’t too much a priority. After reading this that has definitely changed.

  27. My wife and I have been twice since we got married. We actually bought into an “ownership” at a resort. I regret that part, but the only good thing is it makes me take the time to use it. We plan on going back next year. From the time I step off the plane when we come back home, I think about the next time I go. I think about it everyday.

  28. Great comments on here!! Make Hawaii more appealing! :) Looks like I’m gonna head over to Hawaii for about three months in January. I’m a chef that is looking to have a working vacation, does anyone know what island would be best to put roots down for that time? Also rent a room, shack ect…? THX!!

  29. Living in Hawaii is completely different from being a tourist. This is for those who are thinking about moving here. Hawaii is the hardest place to meet people I have ever lived, and I have lived all over the country. I am not the only one who has felt terribly lonely. There are a lot of reasons for it. If you’re going to move here, move with a life partner, and do not expect to make any new friends. (If you do, great, but keep low expectations so you won’t be disappointed.) If you’re in your early 20’s, go with a bunch of friends, and live in a big house together. Otherwise don’t even think about moving here.

  30. I am traveling to the Big Island in a few weeks. I never wanted to go to Hawaii because I do not like over commercialization areas. I am so much more of “want to enjoy what locals enjoy” person. So I talked with a lady who used to be a travel agent and she recommended the big island. I cant wait to get there!

  31. We went to Oahu in December/Jan 2017,we loved it so much that we have already booked for our next trip in July.Loved everything about it, there was a certain buzz in the air,cannot really explain it.Looking forward to being there in 5 months time.

  32. Vanessa Ferguson

    As a 58year old single lady, I wish to come to Hawaii. Am not sure where to head for. Don’t want a loud place but not too quiet. Can anybody suggest where I should head for ? Any suggestions please. Would prefer some where not too far from hospitals. As I am Diabetic for many years. Thank you. Vanessa.✖️????

  33. My older brother invited me to join his family on a trip to Hawaii next month. Hence my search and finding your post. They’ve been before and I’m sure they can show me around. I’ve always wanted to go to Hawaii! Any tips on finding cheap flights? I honestly think that if the earth had organs based on location of land and the ocean, that Hawaii would be the heart of the earth. That’s why people that have been there, seem to want to go back. I’m going to try to get some days off to go. Might just have to use some sick days… Thank you (all) for the info, it’s been very helpful!

  34. I also have a plan to go there in coming holidays to enjoy some time with my friends. I am so happy for it. I hope so that it will be a really great time for us and we will came back with a lot pleasant memories.

  35. Hi Matt,

    Love your posts and not finished reading them all. I share the same experience of wanting to go back to Hawaii as much as I can. I have been longing for it since I was little and had a poster in my first own house that reminded me of that dream. Last year in March I booked a 10 day San Francisco and impulsively checked how far I was from Hawaii and realized it was the closest I would ever be. So I booked a ticket from SFO to HNL for 4! days. It was amazing, I went horseback riding in Kualoa Ranch it was like a dream come true. The day after I rented a Ford Mustang and cruised to Kailua Beach park. I tried to find humpback whales but they were not there on that sunny day. It was clear that a couple of days on O’ahu was not enough so I went back in May last year for another two weeks…to find myself craving to see more islands and so I just returned from a 7 week trip to Hawaii. I have been to Kauai, Maui, Molokai and O’ahu. Saw the Na Pali Coast from birds eye view and from a boat. Hiked the Sleeping Giant, saw many spinner dolphins while kayaking and yes another dream come true: humpback whales. Incredible experiences. So much blessings I lost track of how many whales I had seen. There sure is something magical about the islands and I am sure I will be back to see the Big Island. 3 times in 1 year, I just got back and as I write this I can’t believe it myself. Too bad I cannot work there coming from the Netherlands. But who knows, one day…I quit my job on January 31st to see more of Hawai’i, going to Sweden for a couple of days and after that another 60 day adventure in Indonesia. Happy travels Matt!

  36. I grew up up in Hilo, Hawaii. In a very different time than today, racial diversity was still broad, yet it was always China town or even “Little Japan.” I thought many of your comments were on point, and others a slight miss… O’ahu is far from overlooked and honestly, I tell all those seeking advice on their holiday travels to go outside of the commercialism of Honolulu. There are great differences between the islands, but even greater divides within an island itself. Hilo, Waimea, Waikoloa, and Kona… Four VERY different worlds from a locals’ perspective.

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