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  • Writer's pictureSharon To

A Week in Paradise: My first Trip to Hawaii

It’s been a little over a month now since I took my very first trip to Hawaii (and my first trip since the start of the COVID-19 pandemic)! It was a bit of a ride getting there, and after a cancelled trip in 2020, I finally made it!

It was such a wonderful experience full of sunshine, water, fresh air, and great company! I hope you’ll enjoy following along as I recount the journey with travel buddies and all the yummy foods and great experiences I had throughout the week.

To start off, I wanted to go over what the planning process and the travel day was like before I dive deeper into all the cool things I got to do!


First things first: picking the island. Since this was my first trip, and the first for a number of my friends who I was traveling with, we decided to stay in Oahu. Not only because it’s the most tourist-friendly spot, but also because traveling during the pandemic isn’t the easiest of things, so island hopping was just not a part of our plan.

Before I travel anywhere, I like to get a general sense of what food places, tourist attractions, landmarks, etc. I want to see, put them all on a map, and figure out what’s the best location to stay so that I’m closest to most of the things I want to do in order to reduce travel time. (I try to be as efficient as possible). Of course, when it came to staying in Oahu, we landed on picking a lodging in Waikiki so we could stay close to most of the hustle and bustle. A very good choice in the end - I definitely liked the location of our place.

Here’s a snapshot of what my map looks like while I’m planning. The color-coded pins indicate the groupings for different days’ activities, which is what I do next after landing on must-try’s and adjusting schedules based on different locations’ opening hours.

Snapshot of Oahu with color-coded location pins to indicate routes of the daily Hawaii itinerary


Packing: the bane of my existence. I’m a conservative packer when it comes to travel. I typically don’t pay for checked baggage on my flights so all I have is usually a carry-on and personal item, both stuffed to the brim. Knowing that I wanted to bring home souvenirs though, I had to be careful not to pack too much, since I needed room to bring stuff home. (I gauged poorly, but we’ll come back to that).

Because I try to travel light, it’s important to me to plan out all my outfits, with a few emergency items, and try to anticipate all my hygienic/travel/miscellaneous needs.

Here's a quick and easy packing list I prepared for my trip:

Hawaii packing checklist


When I say I planned my outfits, I planned them. I laid everything out, tried to find ways I could mix and match so that I could reuse some clothes and therefore bring a little less, and wrote each outfit down on my Notes app in my phone so that when I was traveling I wouldn’t have to think about it. This is also where planning out your itinerary early comes in handy, if you’re the type who likes to match your outfit to your activity ;)

I always like to pack extra underwear in case of emergency and because they’re small and don’t take up much room. I’ll also bring an extra pair of shorts and a t-shirt/tank top because you never know. But other than that if it didn’t make a day’s outfit, it didn’t come.


If you plan on doing any hikes in Hawaii, hiking boots are a huge benefit. So many hiking paths are rocky or dirt paved, and, if you’re going during the rain, potentially muddy. Hiking boots give good traction and, at least in my case, were easier to use because I didn’t care if they got dirty since that’s what they were for. I used my hiking boots basically every day and I was so glad to have brought them.

Pro-tip for light packers like me: wear your hiking boots onto the plane. Since you’re only allowed to bring two bags, you don’t want your boots taking up 50% of one of them. Once you’re on the plane, it won’t much matter how many bags you have, so you can swap your boots for a pair of lighter shoes or sandals and carry the bag out with you and your luggage when you deplane.

Bring cheap sandals you don't mind ruining. As much as I loved the beaches in Hawaii, the sand loved my sandals more. Every day we went to the beach, and every day I buried my sandals in the sand and doused them in the sea. Maybe most people don’t care as much about their shoes as I do, but I was about to wear my favorite Birkenstock sandals to Hawaii and I’m so glad I didn’t because they would be absolutely wrecked after the trip. Instead I went to Target and bought a cheap pair of strappy sandals on clearance for $5.99 and had as much careless fun as I wanted and didn’t have to worry at all about my shoes!


I’m pretty big on making sure I capture as many moments as possible. In some ways, it’s arguably not as fun because you’re so focused on taking pictures and videos you’re not in the moment, but it’s something I enjoy so I make sure I have my gear with me. I’m by no means a pro or very good at all at photography, but I do what I like and it makes me happy to look back on the memories I’ve captured.

I always pack my DSLR, memory card, a laptop for transferring photos, and the necessary adapters and power cords. This trip I was actually lucky enough to be using a Canon DSLR with wifi capabilities so I could transfer photos directly to my phone, so I didn’t really need my laptop at all. I brought it anyway because I wasn’t sure if I’d need it in an emergency and I like to keep it handy, but I didn’t touch it at all for the week. That being said, I’ll still continue to bring my laptop with me because it’s still nice to have access to it and you never know when you might need it. I actually bought my Macbook Air in 2019 in preparation for all the travel I was planning in 2020 and never got around to using it for that purpose, so bringing it to Hawaii just felt like a must. And it was so lightweight it wasn’t even a hassle.

And of course if you’re going out and being adventurous, you might also want to bring an action cam. Since I’m not typically a super active person, I wasn’t sure that I wanted to invest in a GoPro anytime soon, so I borrowed my sister’s Polaroid Cube, an action camera that has since been discontinued. But you can find something similar to it that’s still fairly affordable like this Polaroid Waterproof Action Camera. This is especially fun and useful if you’re doing something like ziplining (which I did!) or want to record a hike you’re doing. For hands-free recording, you’ll need some additional gear.

A good external battery is also a really nice thing to bring. I had one hunky one that I left in the condo that I used to charge my stuff overnight or during breaks so I didn’t have to compete with others for wall outlet spaces, and a small one that I brought in my bag wherever I went.


The one item that I am so glad I brought with me was an umbrella. I’m not a fan of baking in the sun. For me it’s bright and draining, it causes me to burn, and I occasionally get rashes when I’ve been in the sun for too long. Don’t get me wrong, I love sunshine, but too much of it just isn’t for me. So I mainly brought it with me to protect myself from the sun. I prefer umbrellas to hats because 1) I don’t like hat hair and 2) umbrellas can cover shoulders and more than just your face, and you can move them around for best coverage whereas hats just stay on your head regardless of what angle the sun is. But the best part of bringing the umbrella was that it not only shielded me from the sun, but it also kept me dry from the rain! I hadn’t realized just how much it rains in Hawaii. Yeah, it only rained for 10 minutes or so at a time, and it mostly drizzled rather than downpoured, but I just prefer to stay dry and shaded. And it really came in handy one day when it straight up rained on us while we tried to hike in the forest. So the umbrella just came in handy for all the kinds of weather that Hawaii had to offer.

The other thing you’ll be so glad you brought with you is wet wipes/baby wipes/hand sanitizer wipes. They are a must, not just because of or during Covid, but in general, it’s nice to be able to clean your hands (or your whole body if you’re going on an ATV tour) when you’re on the go. Hand sanitizer is great, and you’ll definitely still want to bring that around as well, but wipes are nice because you can also use them to wipe down anything else that might be dirty or unsanitary. Especially if you’re coming from a long and dusty hike and you’re about to sit down to a yummy meal, it’s nice to bring out the wipes and get yourself cleaned up before you dig in.

It’s also a good idea to pack some snacks for your travels. You never know when you might be caught somewhere while hungry with no easy access to food, so having light snacks is always a good idea. My flight was around 5 hours long, so I got some granola bars so I could snack on the plane, and brought some extra for potential hiking snacks. I prefer things that are small and individually packaged so they could be slipped into any crevices in your bags/luggage and so they’ll be easy and convenient to carry around.

Booking Flights

Then, of course, we have our flights. As someone with pretty flexible vacation time, I can basically travel whenever I want, but since I was traveling with friends who had some more restrictive schedules, we chose a Sunday-Sunday trip. Because of the pandemic, the flights in general were still on the affordable price range! I was fortunate enough to be able to use my Chase Reward points. Since I was able to build up a lot of points over the course of the past few years I’ve had my card, I didn’t have to pay for my flights at all, and because the tickets were already cheap, I got a fantastic deal! If you’d like to sign up for a Chase credit card, use my referral link here! If you sign up using my link, I’ll receive a referral bonus (and be very grateful!)

Finding Lodging

Traveling to Oahu, there’s no shortage of places to stay. You have options from looking in Airbnb or other travel sites to find rental condos, or you can look for hotels, etc. I definitely think for larger groups it might be better to find rental condos since they can hold more people and your party might want to stay together since hotel rooms accommodate less people per room. But if you’re a couple or you’re traveling solo, a hotel might be the way to go!

Of course, it also depends on what your priorities are. Since it was my first time traveling to Hawaii, as well as some of my friends who I went with, we decided to prioritize location and found a place in Waikiki so that we could be close to more of the places on our itinerary. We were also trying to be very budget-conscious so we picked a bit of an older place that didn’t look quite as spectacular as some others in favor of the price. However, the spot we had was still great, had an awesome view, and had enough space for everyone. Staying outside of Waikiki could give you more spacious options at lower prices but the trade-off would be that you’re not as close to tourist-y spots, and if that’s not what you’re looking for, then perfect!

Safe Travels Program

Hawaii is unique when it comes to traveling during COVID-19 because they’ve established the Safe Travels Program that everyone entering the state will need to sign up for. This is how they ensure that everyone entering is safe and unlikely to spread the virus. Of course, nothing is guaranteed, but it’s a great assurance knowing that everyone getting on the plane either has a negative COVID-19 test result or is vaccinated. After you’ve booked your flights and gotten your lodging, you’ll create a Safe Travels Program profile where you’ll enter in your trip. You can then apply for an exemption to the 10-day quarantine requirement by uploading proof of vaccination, or uploading a negative COVID-19 test result that was taken within 48 hours of your flight. I was fully vaccinated when I flew, so I linked my validated vaccination status through Clear ID and was exempt and ready to go!

24 hours before your flight, you’ll have a health questionnaire in your account that you’ll need to answer before you can receive the QR code that’s needed to obtain the pre-clear wristband at the airport. This is important because if you don’t complete this, you’ll need to go through Hawaii’s health clearance process when you arrive at the airport which looks like a big hassle.

Flying to Hawaii

So now that we got everything out of the way, the lodging’s been booked, the itinerary’s been set, it was time to actually go!

Since I didn’t check any bags, I didn’t have to drop any off at the check-in counter. And because I have Global Entry I was able to use TSA Pre-Check to get through security with ease. My flight was in the morning around 10AM, so I got to the airport around 8:30AM (I like to be early) and there was very few people even in the non pre-check security line.

When you’re through security you’ll need to make sure you get your pre-clear wristband for Hawaii using your Safe Travels QR code. I tried to get mine with an Alaska Airlines agent since that was the airline I was flying with, but they told me to get it at my gate 1 hour before boarding. I followed their instructions, but I did notice other people around me already had theirs and the gate attendant appeared to think that we should have already gotten our bands. So there was a bit of a mix-up there, but we were all able to get our wristbands before the flight in the end, so all was good!

Alaska Airlines Hawaii pre-clearance wristband
Pre-cleared and ready to go!

I was lucky enough to get a flight that wasn’t too full, so boarding didn’t take very long, and there was lots of space between me and other passengers. I actually got a full row to myself which was absolutely perfect! During the entirety of the flight, masks are required to be worn unless you are eating or drinking. My flight on Alaska Airlines offered one snack and two drinks for the duration of the flight, though some other airlines might offer more. If you foresee yourself wanting more than that, be sure to bring your own.

The flight was smooth and seamless, and in almost no time at all, I landed in Daniel K. Inouye airport and into the humidity and warm air that hit me as soon as I stepped off the plane.

I was finally in the wonderful island of Oahu and more than ready to explore the island!

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