| Annapolis to Winder (Georgia) | 527.97 mi (849.69 km) |
| Annapolis to Windsor (California) | 2,467.43 mi (3,970.94 km) |
| Annapolis to Windsor (Colorado) | 1,507.15 mi (2,425.52 km) |
| Annapolis to Winfield (Kansas) | 1,115.11 mi (1,794.60 km) |
| Annapolis to Winnetka (Illinois) | 627.99 mi (1,010.65 km) |
| Annapolis to Winona (Minnesota) | 857.78 mi (1,380.47 km) |
| Annapolis to Winston-Salem (North Carolina) | 285.63 mi (459.67 km) |
| Annapolis to Winter Garden (Florida) | 777.28 mi (1,250.91 km) |
| Annapolis to Winter Gardens (California) | 2,282.47 mi (3,673.29 km) |
| Annapolis to Winter Haven (Florida) | 813.84 mi (1,309.75 km) |
| Annapolis to Winter Park (Florida) | 768.29 mi (1,236.44 km) |
| Annapolis to Winter Springs (Florida) | 760.92 mi (1,224.58 km) |
| Annapolis to Winterville (North Carolina) | 242.83 mi (390.79 km) |
| Annapolis to Winton (California) | 2,374.84 mi (3,821.94 km) |
| Annapolis to Wisconsin Rapids (Wisconsin) | 781.53 mi (1,257.74 km) |
