These Caribbean picks run heavy on all-inclusives and Hyatt properties because you've got a multi-gen crew and no age specifics—which means you need flexibility. Beaches Turks & Caicos leads because it's purpose-built for the widest age spread (toddlers through teens in one property, no compromise), and Grace Bay alone justifies the splurge. If you want all-inclusive convenience without the Sesame Street overlay, Hyatt Ziva Cap Cana offers the same kids-and-teens infrastructure but quieter, Dominican-style. The Aruba and Bahamas resorts are solid if your family prefers villa-style or is tired of all-inclusive sameness, but they'll require more restaurant hunting.