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Rex Kwan Do Dojo
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I have a buddy that chucked it all and moved to an Island in the Bahamas.When he is not fishing he free dives for lobster dinner.It is one of the most relaxing places to live.
That sounds so awesome. My wife would never let that happen.
 

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I currently split time between NC and Islamorada. I've been visiting Islamorada at least once a year for 25 years and, before committing to a purchase down there, I spent a few years "trying out" other areas. I spent very little time on the east coast because it just wasn't my speed and didn't have enough inshore fishing. I tried out Bradenton, Anna Maria Is, Longboat area and Pine Island, Matlacha, Bokeelia, St. James City areas and, while all had their charms, none of them were "The Keys". I've just come to love it there over the years.

I think I had fortunate timing - purchasing my house in the spring of 2019. I probably couldn't afford it now but, if you concentrate on the lower keys - between Big Pine and Stock Island, you can probably still find something of some sort more reasonable.

You just cannot beat the access to different fisheries from the Islamorada area. You could literally catch sailfish, bonefish, tarpon, snook and reds all in the same day (okay, that would be an incredible day but all those fish are accessible). I mostly fish the backcountry but also have a hybrid bay boat that can go to the humps or where ever.

Good luck in your search.

P.S. I also have a buddy that has a place in SW Montana (where Yellowstone is filmed) and I make it a point to get up there each August. I think that's similar to your main locale.
 

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I have a buddy that chucked it all and moved to an Island in the Bahamas.When he is not fishing he free dives for lobster dinner.It is one of the most relaxing places to live.
SOB! Lucky but anyone can do it. I am jelly though as I've thought of that. I think my Wife would go for it until grand kids entered the picture.
 
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