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Taking a Work-Cation on Hawaii's Big Island

Updated: Apr 19, 2023

pololu valley lookout
Pololu Valley Lookout

It's Been a Little While...

How are you holding up? You hanging in there?

I know, the world has been in a bit of a state... it's been a rough one, for sure. As for me, it's definitely been a year of change - new job, new apartment, the whole thing.

Although a lot of terrible stuff happened in the last year, I've realized that a few positive changes came out of the situation. The biggest one for me has been that new job I mentioned. It's at an online company and it's fully remote! As are many jobs at the moment. It seems like a lot of companies are realizing the benefits of allowing their employees to work from home and I can only hope this trend continues even after we return to some form of "normalcy."

But what does any of this have to do with travel or my website? Everything, actually.

A few months ago my boyfriend and I were discussing all the places we would travel to if we could (as one does during a pandemic). And we said that now that we both work remotely, we would try to combine work and travel once it becomes safer. We would bring our laptops with us and we would work from Europe or South America or anywhere else. We'd work in the mornings and explore after work and on the weekends. It sounded like a dream.

And then it hit me. It may not be safe to travel the world at the moment, but what's stopping us from safely traveling within our own country? And that's how it began. We decided that Hawaii was the furthest state we could travel to within the US and that it would feel like international travel without actually having to leave the states.

And within six weeks of sparking the idea, we were on our way to Hawaii.

Working Remotely From Hawaii's Big Island for a Month

This was my first time ever trying to work remotely while traveling. Of course, there were some logistics about working from a timezone six hours behind our own that had to be sorted out - and we had to take the precautionary COVID tests before flying - and we had to make sure that our Airbnb had high-speed internet, etc, etc. You get the picture. Taking a work-cation isn't quite the same as taking a vacation. But that's okay, we knew it would be a different experience and it was all worth it.

We decided to make our home on the Big Island for a month. Normally, when I travel I'm all about movement. I like to backpack, train-hop, and scoot scoot to all different parts of a location. But this time was different because 1) it was a working vacation and we didn't have as much free time as we would on a real vacation and 2) you have to take COVID tests in-between traveling to any of the Hawaiian islands or else you have to quarantine for 10 days. And rapid COVID tests are like $200 a pop so.... yeah. Big Island it was.

The working part of the work-cation isn't necessarily the fun part, so I'll make this quick. Our schedules went something like this:

1. Wake up at 5am. Get ready, have breakfast, drink coffee.

2. Work from 6am-2pm.

3. Get out of work at 2 and have the rest of the day to have fun!

(It didn't work exactly like this every day because occasionally we would have to get up around 3am due to work meetings or because something we wanted to do that day closed early.)

4. Mini-vacation every weekend!

Where Should You Stay on the Big Island

Okay, so when it comes to where you should stay while traveling I'm usually all like, "it depends on what type of traveler you are," or "there are so many different locations to choose from," blah blah blah. When it comes to the Big Island, it's simple. Stay on the Kona side and near the Kona downtown.

The eastern side of the Big Island, or the Hilo side, gets the most rain out of anywhere in the entire US. No joke. It's nearly always raining on the Hilo side. Don't stay there.

We did stay in a bungalow on the Hilo side for a weekend just to experience it and the legends held true, it rained almost the entire time. But there were a few fun things we found to do which I'll talk about in my next article.

So, why should you stay near the Kona downtown and not up near Waikoloa or Waimea? There are a few reasons:

  1. Kona is breathtakingly beautiful.

  2. They say in Kona that if you don't like a beach, then walk 5 minutes to the next one. They have beaches for snorkeling, surfing, boogie boarding, and swimming. Just take your pick!

  3. Many of the water activities take place in Kona. Whether you want to parasail, swim with manta rays, surf, etc. You name it, you can probably do it in Kona.

  4. Kona has farmer's markets, shopping, and restaurants galore!

  5. A lot of Kona is accessible on foot. Or if you prefer, there are bike share stations every half-mile or so.

  6. Kona downtown is about 15 minutes from the Kona airport.

  7. Finally, despite the name, Hawaii's Big Island isn't very big. From Kona, you can drive to the northern tip of the island in about an hour, the southern tip in about an hour and a half, and to the Hilo side in about an hour and forty-five. So Kona is a great home base from which to explore the rest of the island.

A rainbow over Kona Bay in Hawaii
Rainbow over Kona Bay

Things to Consider About an Extended Stay in Hawaii

Expensive Lodging

I'll be the first one to admit, Hawaii isn't the cheapest place to take a work-cation. If you're taking a normal vacation, then you can find a place to stay for much cheaper. If you're taking a work-cation, then you need to make sure that wherever you're staying has fast and reliable wifi, which for us meant renting a condo on Airbnb. We did get a discount for staying for a month, but that doesn't mean it was cheap.

Car Rentals

The next thing to consider is that you NEED to rent a car if you're staying on the Big Island. Much of the island is only accessible by car and without one, you're going to miss out. I recommend booking one online ahead of time because you're not guaranteed a car if you don't, and you can usually get discounts for booking ahead. Also, even though it's tempting to rent that Mustang convertible or a yellow Jeep (so you can feel like Lucy from 50 First Dates), I recommend going with an economy sedan. Gas prices in Hawaii are $1-$2 more per gallon, depending on what your home state is. And when you book online, they don't include taxes so expect to pay hundreds more in taxes and to have a returnable security deposit put on your card.


I already knew and expected this before I went to Hawaii, but food in Hawaii is expensive. Like $7 for orange juice expensive. Like $14 for a small package of deli meat expensive. Like, you'll spend $200 on groceries that would have been $75 at home expensive. Almost everything has to be imported so it's understandable but it still hurts your soul when you're ringing out.

Here are a few things we did to keep our food bill more reasonable.

  1. Get vegetables and fruits from the local farmer's market.

  2. If you shop at Safeway (a large grocery store in Hawaii) then sign up for the Safeway rewards card. It didn't cost anything and saved us $10-$20 for each shopping trip.

  3. We realized that Wal-Mart was a bit cheaper than Safeway but didn't carry as many options. So we got as much from Wal-Mart as we could first then got the rest from Safeway.

  4. Cooking from home is always going to be cheaper than eating at restaurants. That doesn't mean I'm telling you not to eat out. Some of the restaurants in Kona are amazing. But try to limit how much you eat out.

What You Should Pack

Okay, so three years ago I wrote this article on how to pack light, and let's just say that I didn't follow my own advice on this trip and I should have. I was thinking that because I was staying for a month and because I wouldn't be jumping around to different locations, that I should pack more. I was wrong and I ended up packing way too much. This is what I wish I packed:

  1. One pair of sandals and one pair of hiking shoes.

  2. A light jacket because it gets chilly after the sun goes down.

  3. One pair of long pants and 2-3 pairs of shorts.

  4. Four or five tank tops and t-shirts.

  5. Two bathing suits.

  6. One sports bra and one regular bra.

  7. Water shoes (I got these ones from Amazon and they were amazing).

  8. Reef-friendly sunscreen.

  9. The obvious essentials and toiletries.

I way overpacked for this trip and I won't make that mistake again. Even if you're staying somewhere for a month, don't bring your entire closet. You will most likely have a washer and dryer and don't need to bring four bathing suits and five bras (yes, I overpacked that much).

Also, you don't need to worry about trying to pack your own snorkels and fins and such. There are snorkel rental places everywhere and you can rent a high-end set of goggles, snorkel, and fins from Snorkel Bobs for around $11/day. So save the hassle and leave yours at home.

Final Thoughts

Working remotely from the Big Island for a month was a new and exciting experience. I always dreamed of working remotely and having the freedom to travel and work from different locations. I thought this was a pipe dream and that I would have to accept that I'd only be able to take 1-2 vacations every year and spend the rest of my time grinding away. But thanks to us both having remote jobs now, it became a reality much sooner than I ever expected.

If you also work remotely, consider trying a work-cation. Even if it's just for a week, or from a state away. You might find that it opens up your mind to the possibility of something bigger. The change of scenery will be refreshing and it will feel like a vacation without having to take actual vacation time and will break up your daily grind.

My next article will be advice on what activities to do on the Big Island, so look out for that!


If you got to the end of this post, thank you so much for taking the time to visit my page!<3

If any of this information helped you, or if you have advice of your own, feel free to give this post a like, comment, or share!

See you soon!




Backpack Straps
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