The Manhattan grid is the most readable street plan of any major city, which produces a very specific planning failure: everything looks close, so people schedule five neighbourhoods into a day and spend it walking. Twenty blocks north to south is roughly a mile, and the avenues are much further apart than the streets.
Four days covers Manhattan without route-marching. Five lets you spend a day outside it, which is where the argument about what the city actually is starts to make sense.
The most useful structural decision is to give each day a north-south band rather than a list of sights. The subway is excellent for long hops and poor for short crosstown ones, so a day that zigzags will eat itself.
Numbered streets run east-west, avenues run north-south, and the whole thing is easy to read once you accept that the two axes are not the same distance.
New York has four sharply defined seasons and two of them are genuinely uncomfortable. The shoulder months are not just nicer, they are a different city to walk around.
The best weeks of the year
Warm days, cool evenings, low humidity and the parks turning. Prices are high because everyone knows this, but it is the window that makes the walking version of the city work.
Spring, before the humidity arrives
Comfortable and green, with outdoor life restarting across the city. By late June the humidity is setting in.
Unpredictable and much better value
Genuinely variable — you can get either season in a single week — but hotel prices drop noticeably and the museums are calmer. Good for a trip that can move indoors at short notice.
Humid, and the subway platforms are worse
High heat with high humidity, and the underground stations trap it. Many locals leave. The compensation is a dense outdoor events calendar, much of it free.
Cold enough to shorten every day
Properly cold, with wind funnelled down the avenues. Hotel prices are at their lowest of the year, which is the only real argument for it — and a museum-led trip does work.
Peak atmosphere, peak everything else
The city at its most photogenic and its most crowded, with prices to match. Thanksgiving week and the days around the new year are the busiest of the year.
A four-day New York trip needs Premium; the free version covers one destination for up to three days. Generation is unlimited on both.
