Ever since visiting Hawaii for the first time in 2018, we knew that (if we ever decided to stop traveling full-time and pick a home base), that’s where we wanted to plant roots again. Of course, 2020 changed travel for all of us. While it is possible again in many places, it is far more complicated and, for us, much less enjoyable to do full-time. There is already a lot of unknowns in the nomad life, and we really didn’t need any more to throw wrenches in our plans. So, we decided it was time to make the move to Hawaii.
Only one problem … we were trying to do so while visiting family in Florida, without enough reliable income to show as proof for a rental, and knowing Hawaii was probably the most difficult state to get to at the time (due to restrictions and, you know … being across a country and in the middle of the ocean).
The funniest part is, it never crossed our minds that we wouldn’t figure something out. We always do. I think this is partly because we are both impatient and very creative thinkers, so we make quick plans but they are usually pretty smart! But, really, it was mostly divine intervention because it could have easily gone sideways …
(Interested in learning more about our travel life before our big move? Check out Brooke’s book:, Home Flexible: Stories from Life as a Nomadic Traveling House Sitter. Available in print and ebook.)
Making our Long-Awaited Move to Hawaii Work
In general, we didn’t care much where we ended up as long as we were in the islands and off the friggin mainland. We crave the slower pace, friendlier attitudes, and heavenly weather. Initially, prior to COVID, we planned to move with just our backpacks and do farmstays for a while to save up and get a plan to stay long-term. But, since that wasn’t an option, we had to pivot.
I’ve thankfully had a wonderful freelance gig for many years, but it isn’t full-time and not enough to get us approved for an apartment in such an expensive state. So, Buddy looked for remote jobs in his field tirelessly for a solid month with no luck. Then, I had an epiphany – maybe there were options IN Hawaii? Duh! It didn’t have to be remote.
He had a job on Oahu in two weeks, just in time to send his offer letter as proof of income for the apartment we fell in love with in our favorite area of the island – Hawaii Kai. We had toured the little studio virtually and it was leaps and bounds better than anything else we were seeing – plus it wasn’t downtown, which seemed to be the only option for a while (and I was reallllly dreading the traffic, although downtown is still fun!).
We had actually pet sat in this area on our first visit, so we knew we would love it and that finding such a great place, for a surprisingly affordable price, was absolutely a direct answer to all the prayers we were constantly sending up!
On the first week of February 2021, Buddy got his job offer and we were approved for the apartment. A few weeks later he started working remotely, and we were sitting in our new-to-us apartment by March 5th. It was amazing. But, the logistics of getting here were pretty stress-inducing.
Moving to Hawaii During the Pandemic
Going to Hawaii in early 2021 was a complicated and expensive task – especially if coming from the east coast. We had to have a negative COVID test within 48 hours before boarding our plane, but we didn’t have any direct flight options from Florida. So, this meant flying to Phoenix, taking a rapid test that was around $200 each at the time, and stress eating and drinking for 45 minutes hoping we wouldn’t be stuck in a hotel quarantining for two weeks.
Thankfully, we passed! Of course, we had been super safe beforehand (wearing masks any time we were with other people, even though Florida had already basically stopped caring in general), always washing our hands, etc. But you just never know. And testing positive would have meant a really pricey hotel bill and so many tears. I can’t think of many times I was more relieved than when we got those results back.
The next day, we checked our four very heavy bags with our go-to carrier when traveling to the islands, Hawaiian Airlines (they just make those long flights SOOO much nicer for you). Then we collected our colorful wristbands to show we passed the test, which were clearly bought at discount from canceled festival planners. And we anxiously waited to board our flight.
Since we couldn’t get the keys to our apartment until the day after we arrived, we drove our rental car to a hotel downtown and enjoyed a lovely night on American Express Hilton Honors credit card points, ate dinner next door at Waikiki Brewing, and were pleasantly surprised at how relaxed it was.
The lack of tourists at that time was amazing! (Not so much anymore – they are definitely back!) There also may have been some tears of joy when we set our bags down and realized we really freaking made it. The plans came together!
Since we just moved with essentials and clothes, we had to buy all.the.things. when we arrived. Turns out, finding things like a table and chairs, a desk, or a tv stand in Hawaii is a little more challenging since there are less options and many places had (still have) less inventory due to the pandemic. We had planned to do all pre-loved items but couldn’t find ANYTHING that worked for our place, so had to break down and Amazon it.
We did luck out and found a bed in a box at Lowes that we really liked (luckily, that meant only one night on the just-in-case air mattress!). But aside from that, our apartment was sparse for a few weeks. Poor Buddy was working on top of boxes since he was already working full-time when we arrived and the office hadn’t yet re-opened.
Not ideal, but we made it through and were just so very very grateful to be in Hawaii. We also found it funny how easy it was to re-accumulate the things compared to getting rid of it all and downsizing years ago!
Plus, with the restrictions, getting driver’s licenses was actually super easy because we had an appointment that got us in and out! Cheers to that!!!
How Our Car Got from Snowy Colorado to Hawaii (Spoiler: The Hard Way!)
While many things were easier than we thought they would be, getting the dang car out of Colorado was not. Not at all. When we got to Florida after leaving New Zealand in December 2020, we just rented a car for a month to make our life easier and not have to ask for rides everywhere. But, that was expensive AF and we had a perfectly good car in Colorado.
So, after much pushback, Buddy convinced me we needed to go get it since we planned to stay for at least another month. I knew it was the right decision, but man I dreaded that drive. We’ve driven the Colorado to Florida route WAYYY too many times and I loathe driving through Texas.
Plus, it was January so snow was likely at some point. And since it was peak COVID times, we didn’t want to see anyone on our way, so it meant no fun stops … just get the car, unload our storage unit, and get back ASAP. Oh boy!
When we arrived in Denver to pick up our car from Avail (the company who we had been renting it out with for extra money during our travels), we were pretty annoyed that there was some damage we were never told about and some we were told was fixed and wasn’t, but no time to deal with it then. Thankfully, it was all just cosmetic and no issues affected driving because we were trying to get the hell out of there since a big storm was coming in at any moment.
So, we loaded the car with all the random ‘WTF is this for?‘ stuff we had left in our storage unit (that we hadn’t seen for more than two years), grabbed food, and hit the road. And it snowed. And snowed. And snowed.
We made it to Amarillo that night around midnight and it was a harrowing freaking journey to make that happen. The roads were slick, the snow just kept coming, and we were exhausted. But, we pushed through and even stopped on the side of the road in the middle of nowhere to help a family that had hit a deer and could no longer drive their car. We have some fierce guardian angels, I’m telling ya!
Day two of our trip started with digging out all the winter layers that had been buried in our storage bins, and uncovering our car that had been snowed on all night. In Texas … what the heck.
Knowing how absolutely horrible Texas drivers are in good weather, we decided to detour out of the state since more snow was on its way. I wouldn’t have to do the hated drive through Texas after all!
On our way out of Amarillo, we counted at least six cars off the side of the road. And the sun had barely come up. We knew leaving Texas was the best option. And, by the time we got to Arkansas, we had clear skies and open roads. I’m a super nervous driver on the highway, so usually, Buddy does all the driving, but I was actually able to help for a few hours there!
Our plan was to get to Mississippi for the night. Then we checked the radar. They were due for snow by 2 am. It was going to be apocalyptic. Southerners don’t know what to do with snow! We couldn’t stay there. So we drove on. And on. The snow started before midnight in Mississippi – coming down in big fluffy clumps. And we sloshed through it in Louisiana and Alabama, all the way down until Florida.
That night, we stopped in Pensacola at about 3 a.m. We had driven for 19 hours straight in one day (and I only helped with about two!). But I did stay awake the entire time for moral support and to make sure Buddy was coherent. I don’t know how the hell he did it. We slept so hard that night.
Then we finished our drive to my dad’s the next day, thankful to be alive and not seeing snow again for the foreseeable future. We had also made the firm decision to never sell that little champ of a car.
So, we looked up how to ship our beloved Subaru to Hawaii, realized buying a used car in Hawaii was going to be a nightmare and super expensive anyway, and put the $2,700 fee on our over-used credit card to have our car shipped back across the country and put on a boat to Hawaii. We used SGT Auto Transport and they did a great job. Picking up that car about a week after we arrived was a full-on celebration!
What a journey we all had to get here! But, it has been so very very worth it. This is, indeed, where our souls longed to be.
We’ve been living in Hawaii since 2021 and traveling here since 2018. We love sharing all about our adventures and insights on our blog! Read more of our Hawaii vacation ideas, top destinations, and tips here!