Big stars don’t want to be stuck in the middle of a few thousand tourists.
Cruiseships have totally separate cabin areas for crew members, including nice cabins for big name entertainers. There are also separate dining rooms, lounge and recreation facilities. And even within the crew area there can be further division with officer’s facilities and general crew facilities, further allowing privacy for stars as they get to use the officers facilities.
Big stars will board and disembark at the ports that leave them onboard the least amount of time (likely Barbados & Portugal in the OP’s cruise).
The cruise lines and performers are very flexible on this. So, there are several facets to the Answer:
The contracting process is relatively similar for all entertainment so process wise, there isn’t a huge difference between the show performers who are on the ship for weeks or months and the guest performers who do 1, 2, 3 performances.
Carnival is really good at this and they do the same thing with minor comedians.
Often times you will see two Carnival ships in the same port toward the middle of a longer cruise (7 days or longer). There the comedian teams will switch ships. The one that was on ship A moves to ship B, and the one that was on ship B moves to ship A. This gives variety of entertainment to the guests, does not cost the cruise line any additional money, and is only a minor inconvenience for the comedians. If they were on the road, they would have to travel to a new town and hotel anyway.
The same kind of thing could be done for major celebrities who may fly into the port of call. They fly in, get on the ship, do their routine, move to another ship, do their routine, move to a third, fly home.
Doing things this way allows the cruise line to advertise that “Chris Rock” or whoever, is on three cruises rather than one and gets the appropriate sales bump.
Or they might fly in to a port one day and only be on the ship until the next port of call.
Most decks of a cruise ship are spoken for, and there would not be much room for a helipad let alone have the skills for flight operations.
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