| Winchester to Orbetello | 838.27 mi (1,349.07 km) |
| Winchester to Oria | 1,162.72 mi (1,871.22 km) |
| Winchester to Oristano | 906.08 mi (1,458.19 km) |
| Winchester to Orta Nova | 1,051.36 mi (1,692.00 km) |
| Winchester to Orte | 876.86 mi (1,411.18 km) |
| Winchester to Ortona | 953.84 mi (1,535.05 km) |
| Winchester to Orvieto | 854.25 mi (1,374.79 km) |
| Winchester to Orzinuovi | 647.51 mi (1,042.07 km) |
| Winchester to Osimo | 866.31 mi (1,394.19 km) |
| Winchester to Ospitaletto | 645.65 mi (1,039.08 km) |
| Winchester to Ostuni | 1,149.48 mi (1,849.91 km) |
| Winchester to Ottaviano | 1,031.79 mi (1,660.51 km) |
| Winchester to Ovada | 639.29 mi (1,028.84 km) |
| Winchester to Ozieri | 876.02 mi (1,409.82 km) |
| Winchester to Paceco | 1,128.59 mi (1,816.29 km) |
