How to Fail at Life on Maui


I can’t tell you how many people have traveled to Hawaii with their families slash significant others, super stoked to meet up and have me show them around, only to discover that Waikiki, Kona, or Princeville is not actually on Maui. Not even a little bit. So the first way to fail on Maui is not to be here at all.

maui fail at life

But the list doesn’t end there.

How to Fail at Life on Maui

Eat Only at Places You’re Familiar With

The first time I ever traveled to Hawaii was right after high school graduation with my mom and grandparents. And being the habitual eaters they so definitely are, my grandparents could not wait to eat at Tony Roma’s on Oahu. There’s nothing wrong with Tony Roma’s… everyone likes a good rib every now and then, but come on! Traveling several thousand miles away from home to eat the exact same food you eat at home is just plain silliness.

There are several chain restaurants on Maui – Outback Steakhouse, Ruby’s Diner, McDonald’s, Subway, Denny’s, Panda Express, California Pizza Kitchen, etc. – and if you want to eat the same stuff you can find almost anywhere else in the country because you “like what you like”, you can definitely do that. I’m just saying that you’re missing out on tons of amazing local food, and that’s a fail in my book.

Explore Your Resort, and That’s It

I love resorts. They exist for a reason, and that reason is they’re totally awesome. If you say you don’t enjoy sipping alcohol from a coconut whilst dipping your feet in a fancy pool and staring at a white sand beach and turquoise water, you’re lying. The point is, I get it.

best resorts maui

Another point, however, is that you’ve come all this way to enjoy yourself, and beyond taking some time to relax on your beautiful resort beach, that should include leaving and enjoying at least some of what Maui has to offer, which is a ton of things! There’s a volcano, a rainforest, 81 beaches, lava tubes, a winery, a brewery, a lavender farm, waterfalls, botanical gardens, historic sites, festivals, hiking trails, cloud forests, and a giant ocean containing millions of things to look at. Check it out. Explore. Otherwise, you’d be just as happy in Cancun for a fraction of the price.

Overuse Your Selfie Stick

Believe it or not, selfie sticks aren’t absolutely necessary for travel. In fact, I could make the argument that they’re absolutely necessary never. But if you insist on selfie-ing your way through Maui (or life, for that matter), please do your future self a favor and remember to set down your selfie stick in order to use your eyeballs to capture a ‘reverse selfie’, a term formerly known as looking.

People will still believe you were here even if you aren’t the star of every photo you take. I promise.

Rely Too Heavily on a Guidebook

Guidebooks are a great tool for efficiently discovering some of the best things to do and see in a brand new place, but they aren’t meant to dictate your entire trip. If you only eat, drink, do, go and see the places listed in your guidebook, not only does that require a ton of planning and scheduling (vacation bummer alert), but it also narrows your chances of enjoying spontaneous sights and experiences. Make a note about the things you are most interested in, but leave some of your trip open to chance and local recommendations once you arrive. The scenery outside is much nicer than pages 40 to 47.

Let the Ocean Destroy You

Y’all. The ocean is a powerful place. And just because you’re talented at floating on top of it, scuba diving at the bottom of it, identifying fish in it or sailing atop it does not mean you are prepared to swim in it on Maui. The waves can be huge here, and while the most popular beaches are popular specifically because they’re designed not to destroy the average traveler, there are exceptions. Ahem, Big Beach.

When heading to the nearest beautiful beach on Maui, make sure to ‘reverse selfie’ the shorebreak, wave frequency, and intensity for at least a few minutes before going in. The lifeguards will thank you. That being said, don’t be too afraid or embarrassed to ask for help if you’re in danger!

Try to Speak like a Local

Maui is not France. No one is going to get mad at you for not learning how to speak Hawaiian before you arrive. Even worse, some people think it’s necessary to attempt Pidgin, which sounds truly ridiculous unless you know what you’re doing.

If you’d like to add other recommendations for failing on Maui, please feel free to do so in the comments below, and as always, mahalo for reading!

8 thoughts on “How to Fail at Life on Maui”

  1. Being French, I found your last one hilarious. I am very tempted by Maui indeed, thought I didn’t tell many people, because it won’t be supported much. Thank you for making an interesting website.

    Do you think that starting by the main island for a while, then move to Maui could be a good transition, or is not worth the hassle ?

    Thank you,
    Warm Regards.

    • Aloha, Leo! Honestly, if Maui appeals to you, and you believe you would like the island lifestyle, go for gold and head straight here. Don’t get me wrong, the mainland has some really amazing places as well, and it might be less of a culture shock to baby step your way to Hawaii, but I find that Maui is actually filled with very nice people, and that combined with the scenery, weather and relaxed vibe might just make it that much easier of a transition from France. Go for it!

  2. Or you could just get injured and not get any decent health care. I hurt my back and went to the emergency room 3 times before they would give me an MRI and when they did, they scheduled me for surgery. Had to move back to the mainland to get the rest of my surgery done.

  3. 4 years ago I was so upset to see a Famous Dave’s on Front Street. It is a local BBQ restaurant here in MN and WI. ICK!! Don’t want to eat FDBBQ in Maui!! People were lined up down the block. This year it was gone!! Thank you!!

  4. Not traveling the entire Road to Hana. The beauty on the backside is incredible.

    Not driving around the West end.

    You need to learn some history of Hawaii and Maui before you go. I did not my first trip but did after I got home. I have been four times since and the last two times for a month each stay. I appreciate the island so much more knowing the history of the Hawaiian people.


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