July 27, 2021

Preparing to Travel to Hawaii

First, I Need to Commit to a Destination. Why Not Hawaii?

My first big trip post COVID. So much hung in those words and thoughts. I was scared to make a move as to planning. I was still hesitant to get on a plane, so where could I drive from New Orleans that wasn’t 2 days away that I would feel was substantial? Succumbing to my fear (although I denied this to myself at the time) I booked a trip to Apalachicola. I wanted to see a quaint town that wasn’t the typical Florida panhandle commercialism that it’s become. The closer the trip got, the more upset I got about going to Florida for my weeklong holiday. When I saw my friend was in Hawaii, I thought I would ask how it is. Is traveling to Hawaii as beautiful as people say or is it cliche (like I have been thinking for years)? She told me it’s worth it, so I booked my flight and started preparing to travel to Hawaii. I canceled my hotel room in Florida, explaining to the lady on the other end of the phone that I intend to go there one day, just not now. I needed a big trip, and Hawaii was calling my name. “Come see me, Liz. I want to show you what you’ve been missing.” Fine, Hawaii, I’ll see ya soon.

Travel Items to Buy

Is Hawaii Really Worth the 15 Hour Plane Ride?

I’ve convinced myself for years that Hawaii wasn’t worth traveling all that way. Flying for 15 hours to get somewhere that was still the United States felt weird. It took me a little while to mentally get on board with this whole trip, which I’m sure sounds absurd to some of you, but nonetheless I continued to do research and read blog after blog about people’s experiences. What I realized is how diverse people’s experiences are on the same island or from island to island. To get more enthused about preparing to travel to Hawaii, I bought myself a travel pillow, a travel blanket, a travel hair dryer, a dry phone protector, and travel cubes. I admit, it helped. This Hawaii trip was getting better with each click of the Amazon “purchase” button.

So Many Activities to Choose from in Hawaii

As the days went by, I decided to book some activities so we wouldn’t be scrambling when I got there, which is a necessary step in preparing to travel to Hawaii. The first one came with a recommendation from some friends: a boat ride around the Na Pali coastline on the island of Kauai with Blue Ocean Adventure Tours. Sounded fun to me! Another “must do” was the Road to Hana, which is a winding road around the east part of Maui. I was told by two friends to book a hotel room in Hana so that I wasn’t killing myself to experience the whole drive in one day. I booked a room at Hana Kai Maui condos. Additionally,  surfing was on my bucket list of things to do in life, so that was booked as well. Otherwise, I was fine with winging it, specifically regarding restaurant reservations. How hard would it be to find food, at least somewhere? When traveling to Hawaii, or anywhere for that matter, that is a big question for me: book ahead of time or wing it? I went with the latter this time.

Me in a Madewell Dress

What to Wear, What to Wear

After booking the things I decided to do ahead of time, I started thinking about clothes. I like to look relatively cute, I won’t lie. I am not a yoga pants and decent top kind of person on outings. I’m a jeans or dress, cute-ish pair of shorts wearing lady. But, I also want to be comfortable. I bought a couple of new items like a cliche Hawaiian shirt and a dress from Madewell. Preparing to travel to Hawaii was an all-around production. Really, preparing to travel anywhere is for me. I like to be very deliberate. The clothing thing got out of hand, though. It was coming down to the wire of time and I started putting more “fancy” items in there. I had cute sandals, but I just “had” to put a wedge pair in there. And jeans? Is this a joke? I am on islands that are above 80 degrees everyday. I brought two sweatshirts. Bottom line: it was overkill. Below I will list out what is needed, and this is based on my personal needs after the fact.

  1. Swimsuits and cover ups. A cute one, a practical one, and maybe a one-piece. So 2-3 in all.
  2. Shorts. I like Patagonia. Depending on how many days you go, divide it in 2 and bring that many shorts.
  3. T-shirts. I like cute ones. Maybe with wording or a little symbol with a rainbow, but a cute fit. I should’ve brought more. Bring as many as days you’ll be there. They can double as a cover up for a meal.
  4. Sandals. One for the beach and one cute but comfortable pair. Invest in a good pair. Brands I like are: Fly London and Birkenstock.
  5. Sunglasses. A MUST. I am partial to Maui Jim. Aloha!
  6. Tennis shoes. I like to hike. I also like to be comfortable.
  7. Dresses. They make sense because you’re in the tropics. Preferably ones with pockets, but at the least, comfortable.
  8. Comfy clothes. I wish I had brought 3 comfy shorts/pants and a few more t-shirts (as said above).
  9. Jean jacket or similar. For breezy evenings.
  10. Workout stuff. For the hikes or walks. Or if that’s your style.


Preparing to Travel to Hawaii is Easier Than 1,2,3...

That’s about it, folks. Essentials not listed, like bras, underwear, and socks. Hawaii is easy. Preparing to travel to Hawaii is also easy. I made it more complicated than it needed to be, and I want you to avoid that mistake. I know I’ll be back there at some point, so this blog will be a great reference for me, and I hope that if you’re going soon, I helped you narrow some things down. Enjoy your preparations, your excitement, and anticipation for your trip to Hawaii. Please contact me via email if you want to know anything else. I am here to help make this a fun and memorable and stress-free vacation of a lifetime. Also, stay tuned for more Hawaii articles on Kauai, Maui, and all the fun that I had!
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