| Chepstow to Smolyan | 1,461.22 mi (2,351.61 km) |
| Chepstow to Sofia | 1,358.77 mi (2,186.73 km) |
| Chepstow to Sopot | 1,419.33 mi (2,284.20 km) |
| Chepstow to Sozopol | 1,551.51 mi (2,496.91 km) |
| Chepstow to Sredets | 1,533.22 mi (2,467.48 km) |
| Chepstow to Stamboliyski | 1,431.41 mi (2,303.64 km) |
| Chepstow to Stara Zagora | 1,465.33 mi (2,358.22 km) |
| Chepstow to Svilengrad | 1,515.25 mi (2,438.55 km) |
| Chepstow to Svishtov | 1,406.74 mi (2,263.92 km) |
| Chepstow to Targovishte | 1,472.38 mi (2,369.56 km) |
| Chepstow to Teteven | 1,388.68 mi (2,234.87 km) |
| Chepstow to Troyan | 1,408.66 mi (2,267.02 km) |
| Chepstow to Tryavna | 1,441.87 mi (2,320.47 km) |
| Chepstow to Tutrakan | 1,444.04 mi (2,323.96 km) |
| Chepstow to Varna | 1,529.78 mi (2,461.94 km) |
