| Gloucester to Sesimbra | 984.52 mi (1,584.44 km) |
| Gloucester to Setubal | 975.89 mi (1,570.54 km) |
| Gloucester to Sever do Vouga | 822.01 mi (1,322.90 km) |
| Gloucester to Silves | 1,058.06 mi (1,702.79 km) |
| Gloucester to Sines | 1,013.15 mi (1,630.50 km) |
| Gloucester to Sintra | 965.97 mi (1,554.58 km) |
| Gloucester to Sobrado de Paiva | 800.71 mi (1,288.61 km) |
| Gloucester to Sobral de Monte Agraco | 947.62 mi (1,525.04 km) |
| Gloucester to Soure | 871.24 mi (1,402.12 km) |
| Gloucester to Tabua | 841.10 mi (1,353.61 km) |
| Gloucester to Tavira | 1,052.48 mi (1,693.81 km) |
| Gloucester to Tomar | 897.34 mi (1,444.13 km) |
| Gloucester to Tondela | 831.63 mi (1,338.38 km) |
| Gloucester to Torre de Moncorvo | 772.16 mi (1,242.68 km) |
| Gloucester to Torres Novas | 907.98 mi (1,461.25 km) |
