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I spent 5 months there for work several years back. It is a great place for couples as was mentioned. If you want casual in Hamilton try the Pickled Onion. I went there so much that they used to call me Mr Newcastle which was my beer of choice. It has a nice deck overlooking the harbor. If you want a pub, the Hog Penny is right around the corner. I spent most of my time in Hamilton which I am assuming that you are staying there because you're there for work. I would definitely rent a scooter as it is the best way to see the island. I recommend the Swizzle Inn which you will pass on your way in from the airport. It has the best slogan for a bar, Swizzle Inn Swager out. Like others said don't drink and drive a scooter. There are many patches of sand to hit especially when driving on the left. If you decide that you want a very nice dinner got to Ascots at the Royal Palms. That is where I stayed. Have fun.
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