2. San Francisco
San Francisco didn't take cars into account when it was built and hasn't had much use for them since. Cars weren't around when it was incorporated in 1850 or when it was rebuilt after the 1906 earthquake, and protesters didn't see why such a small and transit-heavy city needed freeways running through it during the 1950s. Is it hilly? Yes, but 17 of its neighborhoods still rank among the most walkable in the country. Most are accessible via Bay Area Rapid Transit or the San Francisco Municipal Railway. San Francisco takes great pride in the fact that in everything its residents need are in the neighborhoods around them. Retirees looking to kick it up a notch by hitting street fairs, gallery openings, shows, Giants games or even tourist spots on the wharf or Telegraph Hill won't have to expend a lot of energy doing so.