Headed to Grand Caymen in a couple months for kids senior vacation trip. Was there 8 years ago and have wanted to go back since. Super clean, American speaking, take American money or CI money, fabulous beachess, very safe and American friendly. Doesn't hurt its a British Overseas Island governed by the queen. Drive down the street and go to a Napa auto parts if you feel a little home sick, lol. Not over fished and you get to the "wall" within a mile of the coast so you can go deep see fishing without spending hours to get to deep water. Its a fishermans paridise. 20k ft deep caymen trench is only 12 miles out.
The bad, they drive on the wrong side of the road, it can get little pricey, and the travel sucks. You'll spend 18-20 hours from ND, either on the way there, or the way back because your almost garrettee'd to have a 10ish hour layover somewhere.
also, no all inclusives on the islands. Frankly, I have no desire for that so this fit us great. Rent a beach house and car and make the island your own.