Gezz, that seems a bit to ask someone to do for a joy ride. I would guess he has no idea its a 1500 mile round trip let alone in a 30+ year old car with all the trials and tribulations that could go wrong on the way.
Maybe let him know you have a mileage constraint with your classic car insurance that would prohibit a 1500 mile trip? Although if there's another event like Sebring the same weekend, might be fun. Take a detour to visit the Porsche Center in Atlanta as well.
There is also a pretty terrific museum in Naples: REVS Institute:
https://revsinstitute.org/the-collection/
Plenty of Porsche cars to drool over from the Collier Collection.