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Moving to Caribbean and single

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I am looking for advice on moving from the North East USA to the Caribbean. I am 45 years old, male, retired, single. Looking to live outside the USA for 5-10 years. Don't mind flying back to the states so no residency issues. Not looking to purchase a home would rather rent and continue to move place to place every year or so. Would only work if I needed something to do, not for the money.

I would like to live in an area within walking distance to downtown area. I am not looking for a dating scene but looking for a fun social scene. I have been to many islands and Mexico for vacation but do not have a good handle on what would meet my needs. I would vacation for 2 weeks or more before I move to a certain location.

Questions: What Island would you recommend I should move first? town? What do you see as my challenges? A furnished condo is all I need and would like to live for around $4000 a month.

Does anyone know of areas which are known for non-married people which meets my needs? Thanks

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