Have been to the Cayman Islands on a couple of occasions and stayed at all of them. I like the sister islands, all inclusive, relaxing, healthy food and good value. Diving is some of the best in the Carribean at both for different reasons. The Bloody Bay Wall at Little Cayman is a must. Cayman Brac has its own walls and the Wreck of the Tibbets, plus sites like Grunt Valley with abundant fish.
Grand Cayman offers more nightlife and high end restaurants, but we tend to go casual all but one night. Hemmingway’s was our choice for a date night. In Grand Cayman it seems the diving near Gerogetown is not as good as other locations.
Although we had a great dive at Tunnel Cays (Caves). Stayed at Sunset House and enjoyed the convenience of house reef shore diving. - of course had to see the Mermaid.