Ann Marie,
I have not yet had the pleasure of staying at an all-inclusive (heck, even a hotel) while in the DR. However, regarding your question as to what to wear....
Ladies in the DR would probably NOT wear shorts unless they were headed to the beach and home again. Flip-flops (or thongs, depends on your location) are also not--how should I say this?--culturally appropriate for daily attire, unless you are schmoozing around your room or headed to the beach.
I'm no expert, but have "gone native" in this respect. When travelling in the DR, I wear nice jeans and a top, or a nice skirt and top, and have even worn very dressy clothes for certain occasions. For the beach, I dress way down..I have never been hassled as a tourist, and always feel extremely comfortable and not out of place or a target for an easy buck.
This is YOUR vacation and YOUR anniversary, so please, wear what makes you feel comfortable, beautiful. If that is shorts, go for it. It will scream "tourist"...unless they are linen/cuffed/ creased/ironed, tucked in with a nice belt and sandals. Shorts on ladies are ok if they are like that...
At night, dress nicely, wear some lipstick, and have fun.
My two cents--again, I have never stayed at hotels/AI's.
Happy 28th anniversary!
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