OT: - Short Term Living in Hawaii | The Boneyard

OT: Short Term Living in Hawaii

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Hi all!

Recent college graduate here set to start my job in November - only catch is my job will be remote for the first two months (at least). This got me thinking: what better way to make the most out of work from home than to spend an extended period of time somewhere I've never been? Hawaii was my pick (as most international options are off the table and I figure I won't have many more golden opportunities to spend an extended period of time outside the contiguous U.S.), but I don't know much about which island would be best for me.

A little about myself and what I'd be looking for:

1. Likely going to get a one-month Airbnb
2. Won't have a car, so want to be on an island where I could rent a bike or scooter to get around to attractions and activities
3. Love hiking and biking most, and would really like to see some volcanoes (know Maui has quite a few)
4. Am a big foodie and would love to be somewhere with great local eats
5. Likely will be going alone, so don't want to be somewhere too secluded and lonely

From initial research, seems like Maui meets many of my criteria (especially for outdoor activities, size of island, food, and population density), but wanted to reach out since I figure many here will know more than me, and may also know what part of certain islands would be the best to look at.

Thanks in advance!
 

Mike Honcho

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I hate being the bearer of bad news but Hawaii instituted a mandatory 14-day quarantine back in March and recently extended it until October 1 at the earliest, so it's quite possible you'll be confined to your Airbnb for the first two weeks. You'll also need to fill out a mandatory health form online.

"During self-quarantine, residents and visitors are not to go to any public spaces, including pools, fitness centers, and restaurants."

 

Fishy

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Pretty sure Barbados has a remote worker visa deal these days as well - so does Bermuda.

I don’t know much about any of them other than they are probably nicer than Connecticut.
 
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If you end up going to Hawaii, and settle with living on Oahu, PM me. I’ve got a network of friends who pretty much do the same thing. Oahu is filled with that exact type of people. Want to go see the world while young, end up in Hawaii with no car or real plans but are looking for adventure. My friends there are all mid 20s, love to show people the islands lesser known adventures. They can take you on the best hikes, waterfall repelling, dive spots, secluded areas. Check out ‘exploring_the_808’ on Instagram.
 

CTBasketball

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I would go lower cost of living no?

But if Hawaii is the place check out North Shore of Oahu. I’m bias because I surf but it’s awesome.
 
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I think you'll be surprised at how expensive it is to live in Hawaii, but if its short term and you got some money to burn before work, go for it.
 

August_West

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Pretty sure Barbados has a remote worker visa deal these days as well - so does Bermuda.

I don’t know much about any of them other than they are probably nicer than Connecticut.
Or the Hudson valley
 
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A few years back, I house-sitted for a month in Maui while telecommuting to my job back in the lower 48. It was one of the best experiences of my life. I can give a couple observations (but keep in mind that these are Maui-centric)
1) The time zone change is not a small thing. Unless you can arrange it with your job to start later in the day, which i did. You will be getting up super-early. A 9:00 meeting at EST would be 3AM Maui time. Even with starting late (I was able to start at 10 EST, 4am Maui time), I tended to be half-asleep by sunset.....which isn't a bad thing necessarily, but it tends to put a damper on doing evening activities.
2) If you plan on doing a lot of hiking & enjoying the full scope of whatever island you are on, I'd reconsider the no-car thing. You will definitely be limiting yourself. When I went (4 years ago) renting a car for a month was surprisingly inexpensive. I believe it was under 1K.
Good luck.
 
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I've been to 4 of the islands and think, in theory, it's a great idea. Like others have said, the time difference will be a dealbreaker though.

Other thoughts?

1) What about the Florida Keys? Southwest Flights are 39.00 to Ft Myers right now or a drive down where you'd have your car could be cool stopping at a few spots along the way. Sportfishing, snorkeling, good local food, drinks. It sort of has that island feel.

2) What about something like Utah or Colorado. Take advantage of the mountains, national parks, AirBNB a cool little cabin?
 
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Thanks all for the responses!! Time zone is definitely something I’m still considering. Would have to be savvy about the way I reset it once I get there, but the first week and a half that I’ll be there I won’t be working, so figure that will be a good time to do it. Plus would give me the afternoon to hike and explore.

Will look more into getting a rental car as well.

@spudzj6 @Icculus - thanks for your responses! Between Oahu and Maui, what are your pros and cons? Is there a reason you prefer one over the other?
 

jleves

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I've been to Hawaii several times. Oahu is weird. If you live near Honolulu, it will be like living in any other city in the country. Lots of people, buildings and traffic - really bad traffic. Not sure it would be realistic to bike to cool places. Once outside the city, the rest of the island is pretty low key.

If all you have for transportation is a bike, I would suggest the west side of Maui - either around Lahaina or Wailea. Lot's of things to do and a bike would be rather reasonable for seeing things. A scooter would make things far more accessible no matter where you land.

The only currently active volcanoes are on the big island. Hilo is kind of a dump and has terrible weather. Kona is really nice, but quickly just becomes open country. It's also big, as the name implies. A bike trip from Kona to the volcano would be daunting.

As already mentioned, keep in mind the cost - everything is expensive. Even in grocery stores, most food is about 1.5 times the cost that you are used to. The 2 week quarantine is pretty strictly enforced - don't think that you'll easily get around that. And the time change.

Fishy mentioned Barbados. I spent a few days there and it was really nice. The beaches were every bit as good as Hawaii. I didn't really venture out much, so I can't help with the activities or bike/scooter reasonability. But the time zone is a pro for sure.
 

Waquoit

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I've been to Hawaii several times. Oahu is weird. If you live near Honolulu, it will be like living in any other city in the country. Lots of people, buildings and traffic - really bad traffic
And unimpressive craft beer.
 
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Thanks all for the responses!! Time zone is definitely something I’m still considering. Would have to be savvy about the way I reset it once I get there, but the first week and a half that I’ll be there I won’t be working, so figure that will be a good time to do it. Plus would give me the afternoon to hike and explore.

Will look more into getting a rental car as well.

@spudzj6 @Icculus - thanks for your responses! Between Oahu and Maui, what are your pros and cons? Is there a reason you prefer one over the other?

Long Post Warning!

TL;DR - Hawaii has some negatives, and can be expensive. But when you learn how to navigate it, you will have memories and stories for a lifetime. Hawaii is worth the price of admission if you can find the right people.

Edited to add: yes timezones are tricky, but theres nothing like drinking at a bar with delicious local breakfast food at 6 am for the noon NFL kickoffs!

For all the responses showing the negative side of living in hawaii, or Oahu (honolulu) - what they are saying is 100% true. Traffic is brutal, food is relatively more expensive, beer scene is lacking - especially if you are a foodie, the gastropub type places and casual dining in Hawaii is something that I loved, but not cheap. Grocery store food is a bit more expensive as well. However, every negative characterization can be negated. The biggest and most upfront way to enjoy Hawaii - go out and meet the right people. Quick story: When I was living there, i would research and venture off on hikes by myself. One day i was on top of the Stairway to Heaven (famous stairway climb), which i hiked from the backside through the valleys and mountains. I saw an obscure path down towards a very steep section, figured it wasnt a path at all and started my way back. Out of nowhere, a couple of guys came climbing out of the brush from the steep section. I was dumbfounded how anyone could of navigated that path. Those guys ended up taking me on adventure after adventure, exploring every inch of that island and the amazing wonders it holds. Those guys are now lifelong friends who we plan out adventures and try to top each other. Oahu is full of these types of young twenty somethings that are exploring the world and stopping in Hawaii for months, and most end up making Hawaii their travel "hub" as its between the pacific and mainland US. The vibe between this group of people is absolutely welcoming. Those fun adventures that the tourist industry makes you pay $150-200, are free if you know what your doing. Want the beach? Free. Want to swim/snorkel out to swim with the wild dolphins? Free. Want to go hike the mountains, rock climb, ravine mountaineer, repel down 800 ft waterfalls? All Free (minus the gear). Want to snorkel at the famous Hanama Bay? Free (if you know how the right time to go). If you want a place to stay for a few months, airbnb will get you a somewhat expensive rental, but those groups of "travelers" are always groups of people looking to rent out a room for a month or two. Scooters are sold between friends for cheap as they come and go. You can get one for less than 1k and sell it for the same when you leave. But honestly, if you meet the right people, you find transportation. The bus system in Honolulu isn't hard to learn either. Yes, there are negatives to wanting to spend some time adventuring in Hawaii, but as long as you know what they are, you can find ways to negate them and enjoy your time without worrying about the negative.

As for pros/cons of Maui vs Oahu
- Maui will be more touristy, but less people if that makes sense. It has pretty much everything you have on Oahu, with about half the people. You wont have to wait in line at stores or restaurant (could depend on time of year).
- On Maui, you have less access to cheaper food options, as it's more of a getaway vacation spot than a Oahu (i.e. more permanent residents on Oahu = more affordable food options).
- You might be able to find a better living situation on Maui for cheaper, again depending on time of year. Lots of condos on south side of Maui that owners are looking to fill for longer periods - most people that travel there are week long vacations, so if you want to rent for longer, your more likely to get a good deal. Of course on the south side your farther away from the main hubs of food/attractions) - for reference, they play the Maui invitational on the north side.
- Both islands have great adventures to go on, but Oahu I feel has those adventures more accessible. Maui adventures you will need a vehicle for and more often than not are in deep secluded areas.
- Biking is infinitely better on Maui though. Oahu will give you trouble trying to bike, navigating roads around the island with plenty of traffic and such. Although, i do have some cycling groups out there you can reach out to if you end up on Oahu. Maui just provides a better biking experience (youtube the vegan cyclist and his Maui volcano climbing adventure - talk about epic).

Lots to unravel in my long winded post, so apologies there. Hope this gives some insight. But think the main take away is this - any place you go will have negatives, but the time you spend is only as good as you make it. Yes, Hawaii will be more expensive, but if you know how to navigate it, you'll enjoy it. The wife and I spent 3 years out there, and thats all it took to know we will most likely move back out to one of the islands before we get too old to continue adventuring. Good luck on your travels and let me know if you need help/more info!
 
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Long Post Warning!

TL;DR - Hawaii has some negatives, and can be expensive. But when you learn how to navigate it, you will have memories and stories for a lifetime. Hawaii is worth the price of admission if you can find the right people.

Edited to add: yes timezones are tricky, but theres nothing like drinking at a bar with delicious local breakfast food at 6 am for the noon NFL kickoffs!

For all the responses showing the negative side of living in hawaii, or Oahu (honolulu) - what they are saying is 100% true. Traffic is brutal, food is relatively more expensive, beer scene is lacking - especially if you are a foodie, the gastropub type places and casual dining in Hawaii is something that I loved, but not cheap. Grocery store food is a bit more expensive as well. However, every negative characterization can be negated. The biggest and most upfront way to enjoy Hawaii - go out and meet the right people. Quick story: When I was living there, i would research and venture off on hikes by myself. One day i was on top of the Stairway to Heaven (famous stairway climb), which i hiked from the backside through the valleys and mountains. I saw an obscure path down towards a very steep section, figured it wasnt a path at all and started my way back. Out of nowhere, a couple of guys came climbing out of the brush from the steep section. I was dumbfounded how anyone could of navigated that path. Those guys ended up taking me on adventure after adventure, exploring every inch of that island and the amazing wonders it holds. Those guys are now lifelong friends who we plan out adventures and try to top each other. Oahu is full of these types of young twenty somethings that are exploring the world and stopping in Hawaii for months, and most end up making Hawaii their travel "hub" as its between the pacific and mainland US. The vibe between this group of people is absolutely welcoming. Those fun adventures that the tourist industry makes you pay $150-200, are free if you know what your doing. Want the beach? Free. Want to swim/snorkel out to swim with the wild dolphins? Free. Want to go hike the mountains, rock climb, ravine mountaineer, repel down 800 ft waterfalls? All Free (minus the gear). Want to snorkel at the famous Hanama Bay? Free (if you know how the right time to go). If you want a place to stay for a few months, airbnb will get you a somewhat expensive rental, but those groups of "travelers" are always groups of people looking to rent out a room for a month or two. Scooters are sold between friends for cheap as they come and go. You can get one for less than 1k and sell it for the same when you leave. But honestly, if you meet the right people, you find transportation. The bus system in Honolulu isn't hard to learn either. Yes, there are negatives to wanting to spend some time adventuring in Hawaii, but as long as you know what they are, you can find ways to negate them and enjoy your time without worrying about the negative.

As for pros/cons of Maui vs Oahu
- Maui will be more touristy, but less people if that makes sense. It has pretty much everything you have on Oahu, with about half the people. You wont have to wait in line at stores or restaurant (could depend on time of year).
- On Maui, you have less access to cheaper food options, as it's more of a getaway vacation spot than a Oahu (i.e. more permanent residents on Oahu = more affordable food options).
- You might be able to find a better living situation on Maui for cheaper, again depending on time of year. Lots of condos on south side of Maui that owners are looking to fill for longer periods - most people that travel there are week long vacations, so if you want to rent for longer, your more likely to get a good deal. Of course on the south side your farther away from the main hubs of food/attractions) - for reference, they play the Maui invitational on the north side.
- Both islands have great adventures to go on, but Oahu I feel has those adventures more accessible. Maui adventures you will need a vehicle for and more often than not are in deep secluded areas.
- Biking is infinitely better on Maui though. Oahu will give you trouble trying to bike, navigating roads around the island with plenty of traffic and such. Although, i do have some cycling groups out there you can reach out to if you end up on Oahu. Maui just provides a better biking experience (youtube the vegan cyclist and his Maui volcano climbing adventure - talk about epic).

Lots to unravel in my long winded post, so apologies there. Hope this gives some insight. But think the main take away is this - any place you go will have negatives, but the time you spend is only as good as you make it. Yes, Hawaii will be more expensive, but if you know how to navigate it, you'll enjoy it. The wife and I spent 3 years out there, and thats all it took to know we will most likely move back out to one of the islands before we get too old to continue adventuring. Good luck on your travels and let me know if you need help/more info!
You are the best for this!! Thank you so much! This helped a ton to clarify things for me. I will be sure to reach out if I end up making it out there!
 
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Thanks all for the responses!! Time zone is definitely something I’m still considering. Would have to be savvy about the way I reset it once I get there, but the first week and a half that I’ll be there I won’t be working, so figure that will be a good time to do it. Plus would give me the afternoon to hike and explore.

Will look more into getting a rental car as well.

@spudzj6 @Icculus - thanks for your responses! Between Oahu and Maui, what are your pros and cons? Is there a reason you prefer one over the other?

Unfortunately, I'm a bad person to ask this question. I spent the entire month on Maui exclusively. Part of the house-sitting gig was taking care of 2 dogs, 2 sheep and 4 goats, so I couldn't be gone for more than 8 hours or so at a time. But I generally concur with what spudzj6 says about Maui. But I'm not sure if Oahu has anything that could compare with Haleakala and the Hana Highway, both are like Seven Wonders of the World in my book and living on the island you would have the opportunity to experience them more thoroughly, intimately and at a more relaxed pace than the tourists that come in for their one-week Honeymoons. Maybe that's not enough to sway you one way or the other, but it's worth mentioning.
 
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Everything you stated, other than the biking, screams Oahu. Audit a class at Chaminade University and join the student Adventure Club or Surfrider CUH. You won't regret it. Good people / great times.
 
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Im a current resident of Maui and have lived here for 15 years since college graduation. I love it here however due to covid there is a mandatory 14 day quarantine on all new arrivals. Id say at least 60-75 percent of restaurants are closed. Oahu just issued a 14 day lockdown to try and bring new cases now, no chilling at beach allowed only essential businesses allowed to be open. I would highly recommend waiting till things get back to normal before moving to Hawaii
 
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Hi all!

Recent college graduate here set to start my job in November - only catch is my job will be remote for the first two months (at least). This got me thinking: what better way to make the most out of work from home than to spend an extended period of time somewhere I've never been? Hawaii was my pick (as most international options are off the table and I figure I won't have many more golden opportunities to spend an extended period of time outside the contiguous U.S.), but I don't know much about which island would be best for me.

A little about myself and what I'd be looking for:

1. Likely going to get a one-month Airbnb
2. Won't have a car, so want to be on an island where I could rent a bike or scooter to get around to attractions and activities
3. Love hiking and biking most, and would really like to see some volcanoes (know Maui has quite a few)
4. Am a big foodie and would love to be somewhere with great local eats
5. Likely will be going alone, so don't want to be somewhere too secluded and lonely

From initial research, seems like Maui meets many of my criteria (especially for outdoor activities, size of island, food, and population density), but wanted to reach out since I figure many here will know more than me, and may also know what part of certain islands would be the best to look at.

Thanks in advance!
My nephew has been living in Hawaii about a year as hes in the Air Force and outside of the weather and the scenery he hates Hawaii.
 
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You would not be able to reasonably get around Maui on a scooter or bike. Oahu, specifically the south shore of Honolulu, is the only place you can do that.
 

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