1. Greenwich Village & West Village — Downtown Manhattan, Manhattan
Crooked, tree-lined streets, Washington Square Park and the city's best concentration of jazz and comedy clubs.
The Village breaks from Manhattan's grid with winding lanes of brownstones and townhouses. Start under the arch in Washington Square Park, then wander Bleecker, MacDougal and Christopher Streets past cafés, record shops and the Stonewall National Monument.
At night the area comes alive with landmark jazz clubs like the Village Vanguard and comedy rooms like the Comedy Cellar.
Good to know: The West Village's quietest, prettiest blocks are around Bedford, Grove and Commerce Streets — go on a weekday morning for empty sidewalks.