| The Villages to Hutchinson (Kansas) | 1,112.04 mi (1,789.65 km) |
| The Villages to Hutchinson (Minnesota) | 1,295.80 mi (2,085.38 km) |
| The Villages to Hutto (Texas) | 939.43 mi (1,511.87 km) |
| The Villages to Hyattsville (Maryland) | 752.12 mi (1,210.42 km) |
| The Villages to Hybla Valley (Virginia) | 735.90 mi (1,184.31 km) |
| The Villages to Idaho Falls (Idaho) | 1,939.03 mi (3,120.57 km) |
| The Villages to Idylwood (Virginia) | 742.20 mi (1,194.45 km) |
| The Villages to Ilchester (Maryland) | 772.44 mi (1,243.12 km) |
| The Villages to Immokalee (Florida) | 174.66 mi (281.09 km) |
| The Villages to Imperial (California) | 2,001.68 mi (3,221.40 km) |
| The Villages to Imperial Beach (California) | 2,092.13 mi (3,366.95 km) |
| The Villages to Independence (Kentucky) | 709.48 mi (1,141.80 km) |
| The Villages to Independence (Missouri) | 996.38 mi (1,603.52 km) |
| The Villages to Indian Trail (North Carolina) | 433.26 mi (697.27 km) |
| The Villages to Indiana (Pennsylvania) | 825.36 mi (1,328.29 km) |
