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I would give Miami a shot first. It seems like the logical sequence...Miami first then Hawaii. It's closer, more familiar, and more affordable. You should be able to find something for short term if you'd rather not commit to a full year.
While Hawaii is interesting and everything, I'd probably have to go with Miami this time. Relocating from where you are to Hawaii would be expensive, and if you already earn a decent income you could be able to go on vacation there once a year.
It'd also spare you from island fever.
I lived on Kauai on and off for a couple years with my family outside Lihue. I absolutely love the island. Princeville up north is pretty, but I prefer the southside of the island. However, there's a huge caveat to going to the island. I grew up in exurban areas in the south/southwest- I'm used to not being able to getting amenities all the time and driving long distances to get things. But Kauai really is lacking in just about everything (aside from its natural beauty). There's a safeway on the island now, and there's been a costco there for like a decade or so now? Many areas on the island are undeveloped/hard to access. It isn't just rural, but nothing else is around. You have to fly to a different island for good medical care. Being with a family there is not good as the education is horrendous as well.
However, as a single person in their 20s (you won't meet very many other young folks looking for a relationship on the island) who enjoys nature, it really cannot be beat as far as natural beauty is concerned. The beaches, the mountains, the rainforest.
You may find a better blend on a different island- but you won't find one as scenic. Prices are high on all the islands.
You should visit first before making the move. It is an amazing place, but not for everyone. My expereince is limited on the others- I've never been to Miami (only fort L) and the other islands I've only briefly visited.
Best of luck
I would give the edge to Miami here. I have a couple of friends that lived in Hawaii and while they loved it, same as many posters posted here the isolation and cost of living was too much. Funny thing is both moved to Florida after Hawaii and have been there ever since. Even though Miami is somewhat isolated in it's own way, you are a quick flight from several places within the US AND Latin America. In Hawaii, a quick flight will not take you anywhere other than other Hawaiian islands.
If you are someone that likes to travel a lot and visit different places on a regular basis I would not choose Hawaii then. The cost of living and the isolation will make it prohibitive to travel to different countries and states on a regular basis. If I were you I would think of Hawaii kind of like Alaska. You really are really far out there and isolated. Is living that far out and paying that premium worth it?
I guess it depends what you value. I am moving to Miami next year from Chicago, but I also value my family and maintaining my standard of living. California was an option for me but it is a much longer and expensive flight than Chicago-Miami and a lot more expensive meaning my standard of living would decrease and the my love for travel would also decrease. For me California was not worth it even though it checked so many boxes. So let's say your family lives in the Midwest or East Coast and you visit once a year, you have to be aware that trip will cost you a pretty penny every time.
So just remember Hawaii is paradise but it's also very very isolated and very expensive. Think about how that will impact you. Perhaps it won't, but you definitely need to think about that.
For those in Hawaii, do you really feel like you’re on an island when you’re in let’s say Honolulu or its suburbs?
Yes, absolutely, at least for O'ahu. The island has a mountain range in the middle, so nearly all settlements are along the coasts. This means you're only ever a few miles from the ocean.
I would definitely say Miami. Hawaii is so isolated imo.
As an alternative to Hawaii I would say check out San Diego. That might offer the best of both worlds for you.
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