AARP Bulletin pulled together lists of the most livable large, medium and small cities as well as the nationâs most livable neighborhoods. And the Top 3 in each areâ¦ Most Livable Large Cities: San Francisco, Boston and Seattle. Most Livable Medium Cities: Theyâre all in the Midwest: Madison, Wis., St. Paul, Minn. and Sioux Falls, S.D. Most Livable Small Cities: Theyâre also all in the Midwest: La Crosse, Wis., Fitchburg, Wis. and Bismarck, N.D. Most Livable Neighborhoods: Mifflin West in Madison, Wis., the Upper West Side in New York, N.Y. and Downtown Crossing in Boston, Mass. Madison (which AARP scored a 68), the home to the University of Wisconsin, has been getting drenched with livability plaudits lately.