Originally Posted by
exwannabe
If you take the early morning flight there is a DL operated flight JFK->FCO leaving 7:30PM
SAN-JFK 7:00AM - 3:25PM
JFK-FCO 7:30PM - 10:30 AM
You could also connect via MSP
SAN-MSP 8:30AM - 2:10PM
MSP-JFK 2:51PM - 6:44PM
JFK-FCO 7:30PM - 10:30AM [Departs T4, so no TSA delay]
The JFK connection on that option is still tight (though no worse than your original plans as you avoid the 30 minutes to get to T1 and through TSA). With kids in tow, I would suck it up and wake up early.
Should also point out that the MSP connection is only 41 minutes. If it were me, I would sacrifice the extra 1 1/2 hour of sleep to avoid the stress of not one, but two tight connections with kids in tow. Then I would find a comfortable place to sit and enjoy a late lunch/early dinner at JFK.