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Since this was brought back to life I'll pitch in..
As an avid diver, I don't care much about the Caribbean (the same fish/inverts you see in the Keys you see in the Caribbean), plus you don't have to fly for hours from the US. Never been to HI but I've been to Indonesia (Komodo Isl / Rinca / Flores /Bali), Thailand (Phuket-Phi Phi Isl) and the Mediterranean. I still think the Keys are awesome for a destination you can drive to. The fishing is just as good as HI, the reefs have both soft and stony corals (HI reefs lack soft corals and I believe experienced moderate coral bleaching last year, more than what FL had to deal with). Plus you have one of the best collection of shipwrecks in the world( I recently bought a map and it shows 500+ wrecks for diving, including the second largest artificial reef, the mighty Vandenberg in KW; the largest shipwreck in the world is still in FL, USS Oriskany in the Panhandle). So, to a diver the Keys do not pale in comparison to HI. Maybe to the above places I mentioned, but not to HI.
Topside sure HI boasts mountains which are more impressive to the average person. The Keys are a strip of low lying islands/atolls with fewer options for entertainment/activities(unless you're a diver/fisherman). There's very few beaches for the general population and they are much smaller than the Hawaiian islands or the Caribbean. Comparing FL with them would be a more direct comparison though.
With that being said, I would much rather travel to Southeast Asia or elsewhere in the Pacific than spend my money on HI or the Caribbean. The Keys are good enough for me being so close.
-Weather and climate: Hawaii. It doesn't get as hot as Florida does even in the low lying areas, and in the high areas, you can get some variance.
-Cost of living: If were talking just the Keys vs. all of Hawaii, there are places in Hawaii that are cheaper than anywhere in the Keys (eg, the median in Hilo is around 300K, where anything in the Keys appears to be above 500K.
-Beaches: Probably the Keys for this one, though the rugged coastline scenery of Hawaii is beautiful and it also has many beautiful white sand beaches thrown in. Overall, I'd say even.
-Night Life: This one isn't that important to me, but as a medium sized city, Honolulu is going to have more nightlife than any single place in the Keys. Granted, the Keys have Miami right next door though.
-Local Culture (Latin/Caribbean in FL vs Asian in HI): Depends on preference.
- Isolation: Hawaii is more isolated, which can be either a good or a bad thing. SoFla is quite topographically and geographically isolated also though, which isn't necessarily a good thing.
-Outdoor activities: I'm gonna say HI since the weather is more comfortable, and the hiking that Hawaii has is unmatched by the Keys.
-Water Sports: Not sure about this one, but I might say The Keys. Not sure though.
-Laid back atmosphere: Overall, the Keys, due to size. But, I'm sure you could find very laid back places in HI also.
-Local crime: Gonna give the edge to the Keys, since HI talks about the whole state, and Honolulu has it's not so nice areas.
-Both Natural and Man-Made beauty (like buildings): For natural, Hawaii, easily, due to variety. For Man Made, it's close. HI has more of the ancient tribal history, but Key West has beautiful 19th century architecture, and the Miami skyline blows many places out of the water.
-The only thing that would keep me from saying Hawaii in a runaway is it's isolation. There's something to be said for living in Key Largo and having the isolation and relaxation, but also being a commute distance from a major city, and all of it's offerings, and just being part of mainland US, and not having to buy an expensive plane ticket to go anywhere (or even to other parts of your state.
As far as isolation goes, it's not that big a deal to me, considering that I don't have family in either region... ultimately traveling back to see them would be about as much an affair, one way or the other.
I find Hawaii's geography much more interesting, and am much more familiar and interested in Asian than Caribbean culture. The COL in Hawaii for non-local goods is more steep, but, hey... that's the way the ball bounces. You also don't have to deal with hurricanes on a yearly basis.
I have lived in the FL Keys and never been to Hawaii so can't address that part. But I did want to note that isolation is not really like you think it would be. The first year or so 'on the rock' you go to the Mainland every couple of months but then you settle in. After the first couple of years, if you can't get it there or UPS it in, YOU DON'T NEED IT. that's the thing, adapting to a different lifestyle and mindset. It's not the US south or west, it is the ISLANDS people. Embrace it.
I'm gonna keep this simple. Vacations to Hawaii while living in the Florida Keys. Can't run inland from a sunami in Hawaii.
Actually, in the event of a tsunami hitting the Florida Keys, you'd be a dead man. The highest elevation in all the Keys is 18 feet. Meanwhile, getting to an elevation of 50 or 100 feet in Hawaii is a pretty simple matter.
The history of a tsunami is practically nonexistent in the Florida Keys(not in an earthquake zone though further down Haiti had strong earthquakes in the past) HI is in a volcanic territory and earthquakes are frequent in Japan or other Asian parts(it's in the middle of the open sea, unobstructed by any other landmass ), so it is in more danger.
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