Once on the road in Ancona, the optimum route to Empoli would be as follows:
 1: Start out going SOUTHWEST on VIA VENTINOVE SETTEMBRE toward LARGO CADUTI SUL MARE. 0.3 miles Map  
 2: VIA VENTINOVE SETTEMBRE becomes VIA GUGLIELMO MARCONI. <0.1 miles Map  
 3: Turn RIGHT onto BANCHINA GIOVANNI DA CHIO. <0.1 miles Map  
 4: Turn LEFT onto MOLO SUD. 0.3 miles Map  
 5: Turn LEFT onto VIA LUIGI EINAUDI. 0.2 miles Map  
 6: Take the E55 ramp toward A14 / SS76 / ROMA / PESARO. 1.2 miles Map  
 7: Stay STRAIGHT to go onto VIA FLAMINIA. 1.1 miles Map  
 8: Turn LEFT to take the E55 ramp toward A14 / SS76 / ROMA. <0.1 miles Map  
 9: Turn SLIGHT RIGHT onto VIA CONCA / SP4 / STRADA PROVINCIALE DEL VALLONE. Continue to follow SP4 / STRADA PROVINCIALE DEL VALLONE. 0.8 miles Map  
 10: Turn SLIGHT RIGHT onto ramp. 0.1 miles Map  
 11: Merge onto SS16 / STRADA STATALE ADRIATICA. 3.3 miles Map  
 12: Turn SLIGHT RIGHT onto ramp. 0.3 miles Map  
 13: Merge onto SS76 / STRADA STATALE DELLA VAL D'ESINO. 1.6 miles Map  
 14: Turn SLIGHT RIGHT onto ramp. 0.4 miles Map  
 15: Merge onto A14 toward BOLOGNA (Portions toll). 127.1 miles Map  
 16: Keep RIGHT to take A14 toward BOLOGNA CASALECCHIO / A1 / FIRENZE / E35 (Portions toll). 3.5 miles Map  
 17: Keep LEFT to take A1 toward FIRENZE (Portions toll). 56.6 miles Map  
 18: Take the S.G.C. FIRENZE-PISA-LIVORNO exit toward FIRENZE SCANDICCI. 0.7 miles Map  
 19: Take the ramp toward PISA / LIVORNO / SCANDICCI. 0.1 miles Map  
 20: Merge onto STRADA DI GRANDE COMUNICAZIONE FI-PI-LI. 11.9 miles Map  
 21: Take the ramp toward EMPOLI EST. 0.1 miles Map  
 22: Turn LEFT. 0.1 miles Map  
 23: Turn LEFT onto SS67 / VIA TOSCO-ROMAGNOLA / STRADA STATALE TOSCO-ROMAGNOLA. Continue to follow VIA TOSCO-ROMAGNOLA. 1.0 miles Map  
 24: VIA TOSCO-ROMAGNOLA becomes VIA JACOPO CARRUCCI. <0.1 miles Map  
 25: Turn SLIGHT RIGHT onto VIALE FRANCESCO PETRARCA. 0.1 miles Map  
 26: Turn LEFT onto VIA GIULIO MASINI. 0.4 miles Map  
 27: Turn LEFT onto VIA TINTO DA BATTIFOLLE. <0.1 miles Map  
 28: Turn RIGHT onto PIAZZA DELLA VITTORIA. <0.1 miles Map  
 29: Stay STRAIGHT to go onto VIA DEL GIGLIO. <0.1 miles Map  
 30: Turn LEFT onto VIA COSIMO RIDOLFI. <0.1 miles Map  
 31: VIA COSIMO RIDOLFI becomes PIAZZA DEL POPOLO. <0.1 miles Map  
 32: End at Empoli, Toscana IT  Map  
Total Est. Time: 3 hours, 18 minutes     Total Est. Distance: 212.66 miles  
                                 Advanced OptionsShortest TimeShortest Distance
 Avoid Highways 
 Avoid Tolls 
 Avoid Seasonally-Closed Roads 
 Reverse Route 
If you want to see it mapped, use 
http://www.mapquest.com/directions/europe.adp?go=1&do=nw&rmm=1&un=m&cl=EN&qq=hltF3hzNT9vgCYgFpG%252fDI6Zd139xgLqWl5mHnyn%252b%252b8o%253d&ct=EU&rsres=1&1y=IT&1a=&1c=Ancona&1z=&2y=IT&2a=&2c=Empoli&2z=&r=f    The biggest portion is the Austostrada 14 toward Bologna and then the Austostrada 1 toward Florence. A team that could figure out this route and do it according to the estimated time would have arrived by about 2am, which Nathan and Jennifer may have done. Everyone else was 3 or more hours behind that.