| Chepstow to Orbetello | 909.20 mi (1,463.22 km) |
| Chepstow to Oria | 1,233.89 mi (1,985.75 km) |
| Chepstow to Oristano | 973.43 mi (1,566.58 km) |
| Chepstow to Orta Nova | 1,122.60 mi (1,806.65 km) |
| Chepstow to Orte | 948.06 mi (1,525.75 km) |
| Chepstow to Ortona | 1,025.07 mi (1,649.70 km) |
| Chepstow to Orvieto | 925.45 mi (1,489.37 km) |
| Chepstow to Orzinuovi | 718.74 mi (1,156.70 km) |
| Chepstow to Osimo | 937.47 mi (1,508.71 km) |
| Chepstow to Ospitaletto | 716.83 mi (1,153.63 km) |
| Chepstow to Ostuni | 1,220.61 mi (1,964.38 km) |
| Chepstow to Ottaviano | 1,103.00 mi (1,775.10 km) |
| Chepstow to Ovada | 710.27 mi (1,143.06 km) |
| Chepstow to Ozieri | 944.38 mi (1,519.83 km) |
| Chepstow to Paceco | 1,198.09 mi (1,928.14 km) |
