Hello! Myself (30m) and my girlfriend (29f) are looking for a new destination this year. Typically we spend a few weeks of our winters on the west coast of Florida, but due to the bad hurricanes, our typical destination is still a bit underwater. I've been to Puerto Rico and loved it, but I think I'd like to try something new. Have heard some positive things about Grand Cayman and Aruba, but since I've never been I'm lost as to where to look. Open to anywhere in the Caribbean and excited to hear your feedback! Here's a few other things to keep in mind:

Budget - $500 / night
Happy with resort or local feel
Good food is definitely a must, need good restaurants
Prefer boutique to all inclusive
Need beach & easily accessible golf
Shopping is a +
Prefer to stay on one island
Departing from Boston and prefer nonstop.
Any other fun beach activities are a plus as well

Thanks!

You posted this before and have received several suggestions.
What island is best for us?

Aruba is a great island for a resort experience and also for great restaurants. There are many resorts. We stayed at the marriott several times and enjoyed our stay. Aruba has enough action, gambling, nightlife and also very good restaurants. Do not get an all inclusive there.

Not quite sure why everyone says not to do all-inclusive in the Caribbean, especially Aruba, because there are so many great restaurants there. Can’t one do both, stay at an AI and eat out sometimes? We like to mix things up when we go, we rent a jeep and do what we want each day, after all, we are on vacation!

Of course you can pay for an AI and also pay to go out, but why would you want to pay twice?
With all the good restaurants in Aruba and the ease of getting around, not doing an AI makes perfect sense to me.

If you want lots to do and stunning, incomparable beauty, St. Lucia is the place for you. try staying in a VRBO or Airbnb.

OP has not been on here since February 1st, maybe they have gone by now or at least decided on an island