The West Village

The 1811 grid plan that gave Manhattan its numbered streets stopped short here — Greenwich Village was already a village with its own street pattern and it refused to be redrawn.

So you get West 4th Street crossing West 10th, 11th and 12th, which is impossible and true, and streets that curve, dead-end and change name. It is the only part of Manhattan where you can genuinely get lost, which is exactly why it's the best walking.

• Washington Square Park — the arch, the fountain, chess tables, and a permanent free performance of street musicians and NYU students.
• Bleecker Street west of Sixth Avenue, and the food shops on Bleecker between Sixth and Seventh.
• Grove Court and the corner of Grove and Bedford — the prettiest residential corner in Manhattan.
• Commerce Street, tiny and curved.
• The Stonewall Inn and Christopher Park on Christopher Street — the site of the 1969 uprising and now a National Monument.
• Jefferson Market Library, a Victorian Gothic former courthouse that looks like it was airlifted from Bavaria.

The Village's jazz clubs are the real historical thing — several have been running continuously since the 1930s and 50s. Sets are typically nightly with a cover and a minimum; book ahead for the famous ones, or walk into a smaller room on a weeknight and take your chances.

Eating here is expensive and mostly worth it. The cheaper move is the food shops and counters on Bleecker, eaten in Washington Square Park.