Multi-gen trips need one thing: enough separation so grandparents and kids both have a genuine good time, not just tolerate each other. These picks nail that—Beaches Turks & Caicos and Hyatt Ziva Cap Cana are built specifically for that split, with enough theming and structure to keep kids occupied while adults get actual resort time. All five Caribbean and Mexico properties run the full-service all-inclusive model, so nobody's negotiating meals or activities mid-vacation. Woodloch, the domestic outlier, trades beach for a programmed activity calendar so dense that every age finds their lane without the passport hassle.