Where the cruise wins
Several islands in one week without repacking. Better food in a suite programme than at most resorts. A butler. Days at sea, which many people find the best part.
Cost per day in a Yacht Club suite is often lower than a top-tier resort suite once you count the resort's premium dining and drinks.
Where the resort wins
No motion, ever. Your own beach. No fixed departure time. A big room by default.
Direct flights from Fort Myers to Cancun, Punta Cana and Montego Bay make a resort week simple. A cruise means the drive to the port.
How I decide with clients
I ask what you did on your best trip ever. If the answer was a place, I suggest the resort. If the answer was a ship, or a run of places, I suggest the cruise.
I have stayed at all-inclusive resorts across Jamaica, the Dominican Republic, Aruba and Turks and Caicos. I have also stayed in the Yacht Club and the Haven. I am not guessing either way.