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My opinion on this is going to lean more on the "trip philosophy" you have.
So:
-If you usually end up staying put and going home and being happy, do that.
-If when you've left Negril, you wish you'd been more adventurous, or seen some new things...do THAT.
Life is too short for regrets. Just do it. (Thanks Nike). 
The myth is (I do it too) that you have to have EVERYTHING planned out, before you land. It's nice. But you can alter plans, get a hotel, etc pretty easily when on the ground.
Each and every trip is a chance to explore and put another notch in your belt...it sounds like you are a bit of an adventurer...why not jump in a red plate cab and head out on A1...get dropped off...have a few...meet some people...head back after a few hours..? Not every trip is an overnight or full day....
...for me, I started going out toward Grange Hill two trips ago for a few hours, same to Green Island/Caldwell, overnight to Belmont last reach...this reach Belmont and ??? I dunno. But there will be some new flavor to my trip. Shake it up!
Enjoy the ride my friend!
Last edited by brasi; 03-23-2012 at 12:09 PM.
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