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Best Island to vacation for first timers

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I'm looking to surprise my boyfriend with a Caribbean trip the end of March. He can't take much time off work, so I'm trying to do something to leave Tuesday night and come home Sunday night. We will be flying out of Las Vegas. I have never been to the caribbean, neither has he. I want to go somewhere with really nice white beaches and clear blue/green water. I would like something relaxing yet, we won't get bored. It'd be nice to stay at a place right by the beach or on the beach. Also, somewhere where we won't have to rent a car or a place that is easy to get around. I'm very open for any ideas. I just don't know much about the caribbean and want it to be the best vacation. I don't want anywhere that is way city-like, more down to earth relaxed but still with fun stuff to do. I just don't want to take him somewhere and not have anything to do. We're very easy going and open for ideas. So anything helps! I'd like to keep it around $2,500-$3,000 but will spend more if I feel it's worth the money. Also, I don't know if I should do AI or not. Opinions on that would be fabulous too! I've reserched and reserched but am getting no where, I'm so indesisive and it's hard where I've never been anywhere over there. We don't love Mexico, so that's why I'm thinking Caribbean. Thanks all!

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