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3-4 Day Warm Weather Trip Idea for Solo Traveler (Male)

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Looking to get out of the Minnesota cold for a few days to decompress on a beach. I am a 38 year old male. Looking for something easy (relatively short transfer to property) and a place where a solo traveler wouldn't look completely out of place. Looking to sit on the beach or by a pool during the day and a few drinks at the bar at night. I like all-inclusives, but not a must. Thinking Caribbean, but open to anything I could book for air/hotel for around $1,000. Any suggestions? Thanks!

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