3. St. Augustine, Florida: Year-Round Strolls in the Nation’s Oldest City

For those determined to leave snow shovels behind forever, St. Augustine offers a unique alternative to Florida’s massive, car-dependent master-planned communities.

As the oldest continuously occupied European-established settlement within the borders of the continental United States, the city was literally built for pedestrians long before the invention of the automobile.

The historic downtown features several pedestrian-only zones, most notably St. George Street, where you can wander among restaurants, boutiques, and historic sites without worrying about vehicular traffic.

The terrain is entirely flat, making it exceptionally easy on aging knees and hips. Flagler Hospital provides comprehensive medical services locally, and the warm coastal climate ensures you can maintain your walking routine 365 days a year.