Hawaii – 10 Tips for Your Trip!

hawaii, life hacksYou’re going to Hawaii? Yeah baby!! And if this is your first time, I’m jealous. Let’s be honest, I’m jealous no matter what. There’s something magical about those islands, and that won’t be the first (or last) time you’ll hear that phrase. It sounds like a cliché, but it’s really true! You can feel it as soon as you walk out of the airport; they’re not kidding about that “aloha spirit.” And when it’s your first trip, that magical feeling is that much more pronounced, and at the risk of sounding really lame, it’s AWESOME.

If you’re trying to decide if it’s worth the money to go in the first place, here’s a free tip before your 10 free tips: IT IS WORTH IT. Okay, that’s your free tip – here are your official 10 Tips for Your Trip to Hawaii.


Take an early flight, because you gain time on the flight (you’re flying with the sun). So for instance, if you leave from Los Angeles at 8 a.m., you’ll fly for about 6 hours and still land in Hawaii in time for lunch! Almost no time wasted traveling!


All rent cars are pretty much available at all agencies, so don’t go direct to one of the big boys unless you have some kind of coupon. I’ve had much better luck booking through a discount agency, like Discount Hawaii Car Rental, which is a great company with a presence on all the islands. You might want to spring for the convertible on this trip, though! It’s not as expensive as you might think, comparatively speaking.


Even though the weather never changes all that much, it’s generally rainier in the winter. Many areas are  almost always sunny anyway, but summer is still a better time to go. The waters are calmer for boat trips (many don’t even happen in the winter because of rough seas), and the days are longer. But if you go in September, you miss the summer crowds, without giving up the summer weather. Although, there will be tourists everywhere at all times of the year – just less concentrated if it’s not officially summer. If you can’t make it in September, don’t worry about it, it’s un-freaking-believable any time of the year.


Believe me, watching the sunset in Hawaii is a thing. A big thing. You won’t want to miss even one while you’re there. You’ll actually see people ignoring it every night, but here’s a little secret about those people – they’re dumb. Almost every sunset is spectacular, no matter what. The sun sets kind of early there, so it creates a problem if you don’t like to eat dinner on the late side, or on the early side – ha. We like to plan our days around where we want to watch the sunset from on each particular night; and it’s likely that no matter on which island or where you’re staying, you’ll be close by several great sunset-watching spots. Scope them out, and take advantage! Free tip #2: you’ll still be on an earlier body clock when you get there, so go ahead & get up for the sunrise. You don’t go to Hawaii every day, so make every second count. Don’t sleep in! You can sleep when you’re dead.


Duh. But for real, once you get there, you’ll find out that leaving is a VERY SAD EVENT – so you’ll want to put it off as long as possible! Seriously, I came pretty close to crying as a grown man the first time we left. If you can afford it, 10 days is great for not feeling cheated when it’s time to go. My last trip we stayed 19 days, and it went by in a flash! I went on one trip for 5 days, and it seemed like no time at all. It’s worth it to spend a little more time saving up & booking a longer trip.


The fresh produce they sell is all really fresh, and grown by local farmers. If you’ve never tasted a fresh locally-grown Hawaiian pineapple, you’ve never really tasted pineapple. It’s about 100 times better than any other pineapple you’ve ever eaten.


It’s a different vibe out in the middle of the Pacific – slower, easier, more chill. Especially in the smaller towns (which is pretty much all of them except for Honolulu Hawaii). For example, on Kauai’s north shore, there are a bunch of one-lane bridges, and you basically have to take turns on the honor system. And the crazy thing is – it works! You would be risking your life if you tried that in most American cities, but on Kauai, life is different, and nobody gets uptight about it. So get ready for that, and join right in. It’s a wonderful thing.


It costs less than $100 per person generally, and you’ll find out that you can do it! It’s a lot easier than you might think to catch a wave, especially with a teacher helping you do it. When you feel that board swell up underneath you and take off, even if it’s a little baby wave, it’s pretty great; and you start to understand why some people just chunk it all & never go home. That’s probably a bad idea in most cases, but I promise you’ll find yourself thinking about it!


Buy a guidebook – my favorite is The Ultimate Hawaii Guidebook (there’s one for each island). The writers continually do exhaustive research (that’s gotta be a tough gig), and they do a great job of guiding you to cool spots and hidden treasures. If you stick to the commercial tourist-trap spots, you’ll miss the best stuff. Pick several cool-sounding attractions & plan trips to them, and then actually do them. It’s why you go to Hawaii!


You’re going to have to fly all night to get back anyway, so leave late, and get the extra day at the end. You’ll have to check out in the morning, but most hotels offer a free room to shower & freshen up in before the flight home, even though you’ve already checked out. I always milk it for every second, because this trip is not something you do every day.

There are a million tips I could give you, but there’s your Top Ten. If you get to go to one of the Hawaii Islands at all, you’re one of the lucky ones. You’ll catch yourself looking around for a way to make a living there, but I’ve been told you don’t want to move there without a million dollars in cash. Doesn’t stop me from thinking about it, though!




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