| Winter Park to Orbetello | 5,036.61 mi (8,105.64 km) |
| Winter Park to Oria | 5,394.21 mi (8,681.14 km) |
| Winter Park to Oristano | 4,979.63 mi (8,013.93 km) |
| Winter Park to Orta Nova | 5,278.75 mi (8,495.33 km) |
| Winter Park to Orte | 5,090.79 mi (8,192.84 km) |
| Winter Park to Ortona | 5,187.32 mi (8,348.19 km) |
| Winter Park to Orvieto | 5,070.73 mi (8,160.55 km) |
| Winter Park to Orzinuovi | 4,899.27 mi (7,884.62 km) |
| Winter Park to Osimo | 5,112.29 mi (8,227.44 km) |
| Winter Park to Ospitaletto | 4,901.59 mi (7,888.35 km) |
| Winter Park to Ostuni | 5,384.43 mi (8,665.40 km) |
| Winter Park to Ottaviano | 5,235.56 mi (8,425.82 km) |
| Winter Park to Ovada | 4,860.02 mi (7,821.45 km) |
| Winter Park to Ozieri | 4,981.57 mi (8,017.07 km) |
| Winter Park to Paceco | 5,227.93 mi (8,413.55 km) |
