Moving to Hawaii in your 20s

Have you always dreamed of going to Hawaii? I always thought it would be an awesome thing to do, ever since I was small. But I never actually thought I’d make it out there. At this point, I’ve now managed to make it to the islands twice, and have been to Maui, Kauai, and Oahu. The good news is, you can do the trip, too! Even as a twenty something just getting your feet on the ground, transitioning in-between careers, and still struggling to pay off your student debt –it is possible.

The islands are a bit expensive. And if you want to, you can blow a ton of money on the trip. But you don’t have to. Being smart about when and how you purchase your airline tickets can really cut down the cost of getting there. And once you are there, renting a condo can cut down the cost of living as opposed to paying for an expensive resort. Having a condo also means having a kitchen/cooking space so you don’t need to eat out for every meal.

First off, you are going to have to choose which island you want to go to. If you’ve read anything about Hawaii, you’ve probably by now realized that there’s a pretty major difference between one island and the next. Each one offers unique benefits, advantages and experiences. So how do you know which island is right for you?

Let’s start with the two most visited islands: Maui and Oahu. One major advantage of having your vacation on either of these islands is that airfare is probably going to be a little bit cheaper getting there for the fact that they are more commonly traversed. The cheapest tickets I’ve found yet to get to Hawaii indeed were with Hawaiian Airlines going to Oahu.

So what is it like on either of these islands?

When my wife and I went to Oahu, we expected it to be more or less the same as Maui, just with the advantage of having a sprawling city nearby. Funny enough, Honolulu isn’t actually really a sprawling city. In fact, it’s closer in size to Pittsburgh, PA (another of my favorite cities) than it is to a really major city. So for me, having lived in major metropolitan areas, Honolulu did not actually seem to boast all that much in terms of diversity of experiences. In fact, most of what there seemed to do to me (as an outsider and newbie to Oahu) was focused around Waikiki.

Don’t stop reading there. There is much more to do and we’ll get into that in a moment. But first, I really think we should talk a little about this whole Waikiki thing since that’s one of the first places we often think about when we think about Oahu in the first place.

For starters, it’s hard for me to really explain what Waikiki is because it seems to spread out pretty far along Oahu’s coastline. But just in an attempt to put it into layman’s terms, Waikiki is a big area with several different beaches along the southernmost side of Hawaii. Although in the winter months the waves come in swells around the northern side of Oahu, the advantage of the Waikiki beaches is that they stay calm and are great for swimming even in January.

We quickly found this out after our foray into the north side of Hawaii proved too daunting in terms of the waves for any sort of casual swimming/wading in the water. It’s probably great for surfers. I haven’t had time to learn to surf, however.

So along Waikiki, you can lie in the sand. You can swim in the water. You can surf on the waves. You can shop in the shops. You can stay in a nice resort. You can eat out at a few nice places, or get drinks in a few nice bars. And that’s about it. Those are your options for casual fun in the most famous beach of Hawaii.

Here are a few problems I have with the beach though

And I may come off as a little bit spoiled or jaded because I am. I grew up in California and spent summers in both the north beaches and the southern beaches and so have been heavily exposed to the beach life. My main problem with the whole Waikiki scene is that, when compared to other cities and beach towns, it just doesn’t really stand out all that much. Here is why.

There’s really not that much variety

Unless you really love big fancy resorts and lots of tourists, I didn’t find there to be a refreshing variety of bars or places to eat. For the most part, everything seemed relatively the same. Compare this to somewhere like San Francisco where the options are limitless and I just am not sure that it really holds up.

The beaches are okay

Waikiki reminds me a lot of the beaches you can find in and around Orange County or Southern California. They’re nice. They’re accessible and swimmable. The water is not too cold. And there’s a lot of people. But if you didn’t really know any better, you could be in SoCal on the beach. It’s pretty much equivalent. Only, less options in terms of places to eat out etc…

If you want a place with a lot of people around and you like the whole see and be seen scene, then you might like this area. But then again, you are just seeing and being seen by other tourists so I’m not sure if you have all that much to gain from that either.

The Dole Plantation is a little Dull (pardon the pun)

I was not all that impressed with the other little sights around the area, either. The dole plantation was not so different than many places that you can visit along the road in California. Pearl Harbor is a historic site, but it’s not really a feel good location –I think only real history buffs would be drawn to it. A

And the hotels themselves are nice but not as nice as hotels you would see in Las Vegas.

All-in-all, I don’t really see how Oahu holds up as a really unique travel experience –it has a little bit of everything, but it’s definitely outdone in each of its categories by other locations. But you can go if you want to and see what the fuss is all about. Maybe I’m missing something. At the very least, it’s a good winter get away if you live somewhere with horrible weather. Even compared to the Bay Area (we’ve been going through a storm) it was very welcome to have a full week in the sun.

The island for the newly wed and nearly dead. Whoever said that must have been getting paid by Oahu tourism companies. Because there is certainly plenty to do in Maui that make it even more enjoyable than the more popular Oahu.

Maui is the second biggest island in terms of sheer size, and the second most visited. Basically, you get everything that you would get in Oahu, minus the bustling night life, in exchange for a lot more. Let’s dig a little deeper into that.

The Aloha Spirit is Real

In Maui, you really feel welcome. Not only is the whole island basically one giant suburb, but it has a more small town sort of feel as opposed to the dichotomy of city and country that you get in Oahu. For this reason, you can pretty much stay anywhere on the island and get the same kind of experience –beach life with small town living life. Really, it’s pretty cool that way.

People are also much more friendly in Maui. As a tourist, you really feel welcome, which is not very common. I can only imagine this is because, unlike Oahu, there probably is very little income that doesn’t come from tourism. So most people probably have family members who work in tourism and they respect the profession. In fact, you really get the feeling that the people who work in tourism in Maui actually feel like it is their PROFESSION. This was such a refreshing experience for someone like myself who hadn’t every really experienced that before. They take pride in serving and treating tourists like guests and friends.

The Island Feeling is Real

When you are in Oahu, you feel like you could be pretty much anywhere. People aren’t all that friendly. Beaches are crowded. The city isn’t all that remarkable looking. And the countryside is not terribly inviting. I really did not get the feeling that I was away on a tropical island experiencing a different kind of lifestyle or way of looking at the world.

Maui is different that way. It feels like an island. You don’t feel like you are just anywhere else. You feel like you are actually experiencing a different way of life. And it may not be the way of life that you are going to want for the rest of your life, but it is a nice change of pace from the hustle and bustle of everyday life in the mainland.

Maui is More Affordable

There are a lot better options for cheaper accommodations in Maui while also remaining close to the beach. If you aren’t into ridiculous and kitschy hotels and just want a crash pad from which to launch your Hawaiian exploration, Maui is definitely a better option.

There’s plenty to do outside –snorkeling adventures to go on, great sites to see from the road, and awesome beaches everywhere. And that brings me to my final point. Maui offers something unique that makes it stand out, whereas Oahu just contains things that you can get better somewhere else.

Maui really is one big, tourist friendly experience that anyone can enjoy, and offers the get-away island experience that really makes you feel like you are away from it all in a way that Oahu just can’t deliver.

So in that vein, I would say Maui is the perfect island for the newlywed, the nearly dead, and everyone in between –and the ultimate exploration getaway for twenty something!

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