| Castiglion Fiorentino to Smolyan | 662.02 mi (1,065.43 km) |
| Castiglion Fiorentino to Sofia | 577.68 mi (929.68 km) |
| Castiglion Fiorentino to Sopot | 649.53 mi (1,045.32 km) |
| Castiglion Fiorentino to Sozopol | 800.36 mi (1,288.05 km) |
| Castiglion Fiorentino to Sredets | 776.04 mi (1,248.92 km) |
| Castiglion Fiorentino to Stamboliyski | 644.94 mi (1,037.93 km) |
| Castiglion Fiorentino to Stara Zagora | 697.16 mi (1,121.97 km) |
| Castiglion Fiorentino to Svilengrad | 734.04 mi (1,181.32 km) |
| Castiglion Fiorentino to Svishtov | 672.90 mi (1,082.92 km) |
| Castiglion Fiorentino to Targovishte | 736.50 mi (1,185.29 km) |
| Castiglion Fiorentino to Teteven | 622.76 mi (1,002.24 km) |
| Castiglion Fiorentino to Troyan | 645.65 mi (1,039.07 km) |
| Castiglion Fiorentino to Tryavna | 685.13 mi (1,102.61 km) |
| Castiglion Fiorentino to Tutrakan | 734.86 mi (1,182.65 km) |
| Castiglion Fiorentino to Varna | 803.51 mi (1,293.13 km) |
