| Guisborough to Smolyan | 1,474.39 mi (2,372.81 km) |
| Guisborough to Sofia | 1,370.16 mi (2,205.06 km) |
| Guisborough to Sopot | 1,423.95 mi (2,291.62 km) |
| Guisborough to Sozopol | 1,544.11 mi (2,485.00 km) |
| Guisborough to Sredets | 1,528.58 mi (2,460.01 km) |
| Guisborough to Stamboliyski | 1,441.20 mi (2,319.39 km) |
| Guisborough to Stara Zagora | 1,467.29 mi (2,361.37 km) |
| Guisborough to Svilengrad | 1,519.65 mi (2,445.64 km) |
| Guisborough to Svishtov | 1,400.51 mi (2,253.91 km) |
| Guisborough to Targovishte | 1,463.51 mi (2,355.29 km) |
| Guisborough to Teteven | 1,393.52 mi (2,242.65 km) |
| Guisborough to Troyan | 1,411.55 mi (2,271.66 km) |
| Guisborough to Tryavna | 1,441.11 mi (2,319.24 km) |
| Guisborough to Tutrakan | 1,428.47 mi (2,298.89 km) |
| Guisborough to Varna | 1,515.30 mi (2,438.63 km) |
