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Single, Female Traveler - Pick an island

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I am a single female from NY in my mid-30's and enjoy traveling by myself. However, picking a Caribbean island is so hard because I am swimming in choices. I am hoping you all can help with picking an island and maybe even suggest hotels. Below is a lot of information, which I am hoping does not come off as stand-offish but more as helpfulness.

My budget is 2000 for 5 nights/4 days including the flight.. It could be 4 nights/4 days if the flights work out right. I'm looking at either a last minute trip, end of May, or maybe sometime in the fall, taking my chances on hurricane season. I am thinking AI or non-AI. My ultimate goal is to really relax and not exploring much. I want to sit by a nice pool and hopefully the on-property beach that lets me see my toes-in the water, however, if that's not possible the pool overlooking the ocean will work (and if there is a lazy river pool even better). Would really love to go horseback riding on the beach, maybe a hike, a walk if there is a boardwalk or close stores nearby as I will not be renting a car, and perhaps a fun sailing class. But overall the hotel is where I plan to spend most of my time.

I've already been to the Caymans, Jamaica, Bahamas, and Cozumel and while I have not explored every inch of those my preference is to not go back. I have thought of Puerto Rico but I am thinking there is so much to see and explore I'll need another vacation. However, if I am wrong please tell me.

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