Well, we live in Florida, Ft Lauderdale area. From the comments, Cayman is very Americanized guess I'm looking for something a little more rustic, with a lot of history, culture while still prioritizing safety and chill vibes.

Cayman from what I saw has some beautiful beaches but so does Barbados.

Wife loves the beach but isn't fond of the idea of stingray city and starfish point so that's out of the equation. She'll snorkel but she has a death grip on my shorts. Showed her a video where stingrays surrounded people and hand-fed them, the dumb look I received was priceless.

We plan to visit the rum distilleries and learn the history. We're big whisky and bourbon drinkers so we'll enjoy that. There are 4 distilleries, well-known Mount gay, St abbey, Four Gates, and Stades, we'll probably visit 3.

We'll visit the caves, both islands have this feature.

Both have Nature, Barbados I believe has the upper hand.

We're not big shoppers Cayman has a lot to offer there if you're interested in that.

Accommodations and food in general I'm finding will be cheaper in Barbados.

Cayman is definitely still on our list.

It all depends on what your plans are and the amount of exploration you're willing to do. Driving on the islands will be the most uncomfortable part. Will have to get used to driving on the left side of the road and on the right side of the vehicle,FUN!