New York in July is the city at its worst. Ninety degrees on the sidewalks, ninety-five in the subway platforms, tourists in packs everywhere south of 42nd Street, restaurants operating at 40% capacity because half the staff is at the Rockaways. If you have never been, do not book a July flight. You will get a lopsided idea of what the city actually is.
The two windows I recommend: mid-October and mid-February. October is the New Yorkers’ favourite month for reasons that will be obvious the moment you step outside — light is amber, temperature is 60 degrees, everyone is in a wool coat and a mood. February is the sleeper pick. It is cold enough to keep tourists home but not brutal, museums are empty, you can walk into any restaurant, hotel rates are 40% of summer.
What you lose in February: outdoor everything. What you gain: the actual city. New Yorkers in February are chatty because everyone is bundled up and there are no tourists to compete for their attention. Bartenders remember you between visits. You can spend 20 minutes at a Whitney exhibit without someone standing behind you. If you can layer, do February. If you cannot, do October. Do not do July.