Let's say this is an imagined story to protect all the guilty parties .... in the story it happened quite some decades ago.
Two ship civil jump from a near major city regional DZ. Pilots one ex-, one current airline chaps.
Wx plenty of cloud at all levels .. more or less VMC at any level ... but not much in the way of glimpses of the ground. Wind fairly strongish away from the city area.
Dropping from within CTA with a clearance along the lines of "remain within 3 nm of XYZ DZ". Level around 12,000 ft.
Two ship in battle form. One had an ADF with two only basic instrumentation. (The ADF, with no local aids, proved pretty useless for keeping position reference the ground but the pilot, being an old airline checkie, knew it all).
They spent the next 30-40 minutes going around in a nominal holding pattern trying to get enough of a ground sighting for the jumpmaster to give the nod.
ATC folks, on radar, must have been shaking their heads and chuckling away .. fortunately the airspace the two ship was in was not near any busy activity .. the air routes were around 15-20 nm, upwind and closer to the city area.
To cut a long story short, a gap came up, the jumpmaster became confident of his spotting, two moved into close form, and the bunch departed. Both ships separated as briefed and descended through the cloud cover .... you guessed it ... popped out visual with NO idea where they were .. quick check of the chart and they worked out they were around 40 nm SE of the DZ ... once the jumpers got on the ground and found a phone a pickup was organised and they got back to the DZ several hours after the jump.
Was is silly ? .. of course it was.
Messages to take away ..
(a) if you are DZ local transit flying in strong wind and significant cloud cover conditions (especially), make sure you have comms with the DZ/ drop planes to organise self separation. It isn't all that hard to do your homework to make sure you have phone and frequency info.
(b) forget sighting the jumpers in freefall ... and be very wary of the jump plane on descent .. max rate and, generally, reasonable IAS.
(b) playing I/F with no aids and no useful ground contact is not real bright in the overall scheme of things
.. and, having done my good share of glider towing as well as jump flying ... the same comments apply if you are transit through/near gliding activity.