Well,
are you scared about ?
Listen at this schedule Air Italy ( a charter company operating from milano mxp to the caribbean).
Dep from MXP , 13 hours flight to La Romana ( with a B 757 ! yes seven five seven) stop in santa maria (azore island) to refuel.
Arriving mid afternoon in La Romana.
Wake up something like 5 a.m following morning, shuttle flight to Samanà,
depart to MXP, other 13 hour on a 757 with the same stop in santa maria.
Came finally to mxp at 3 a.m. local time
it is enough ?
I forgot, crew of 2, no relief pilot.
Cheers
L.