| Chepstow to Sesimbra | 963.41 mi (1,550.46 km) |
| Chepstow to Setubal | 954.88 mi (1,536.74 km) |
| Chepstow to Sever do Vouga | 800.77 mi (1,288.71 km) |
| Chepstow to Silves | 1,037.65 mi (1,669.94 km) |
| Chepstow to Sines | 992.30 mi (1,596.94 km) |
| Chepstow to Sintra | 944.60 mi (1,520.18 km) |
| Chepstow to Sobrado de Paiva | 779.44 mi (1,254.38 km) |
| Chepstow to Sobral de Monte Agraco | 926.33 mi (1,490.78 km) |
| Chepstow to Soure | 850.01 mi (1,367.95 km) |
| Chepstow to Tabua | 820.19 mi (1,319.97 km) |
| Chepstow to Tavira | 1,032.62 mi (1,661.84 km) |
| Chepstow to Tomar | 876.38 mi (1,410.39 km) |
| Chepstow to Tondela | 810.64 mi (1,304.60 km) |
| Chepstow to Torre de Moncorvo | 751.71 mi (1,209.75 km) |
| Chepstow to Torres Novas | 886.97 mi (1,427.44 km) |
