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Help with choosing a Caribbean Island to visit in March

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I have been receiving some very helpful advice for a Hawaiian trip I am planning for next summer, however my boyfriend and I (in our 30's) have 5 nights to travel somewhere towards the end of March.

We are looking to go somewhere in the Caribbean. He has been only to Mexico, where I have been to Bahamas (Atlantis) Anguilla (Viceroy) and on three Caribbean cruises. We are looking to relax by the pool/beach, jet ski, snorkel, eat/drink, and visit the spa.
We do not gamble, we are not looking for a nightclub scene, would prefer live music. If the island is safe and has a downtown area we may take a few hours to walk around it. We would prefer a resort that may not be full of children as we are both teachers and enjoy the break every now and then. (although it would never stop us from going to a resort)

Is it worth looking into an all inclusive? I have never stayed at one before except for cruises.
What are some resorts to look into? We would be able to spend up to about $600 on a room per night, however would like to try not to spend that much. We will be coming from Newark NJ so having a nonstop would make things a lot easier with only 5 nights.

Would love to hear any ideas and advice. I have been doing so much research and my head is starting to spin. Thank you!

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