New Orleans
The most distinctive city in America, and the easiest to plan badly.
Pick two neighbourhoods a day and stop trying to do the rest.
New York punishes over-planning. The classic mistake is a list of landmarks scattered across four boroughs and a day spent underground moving between them. The city is far better consumed in slices: one neighbourhood in the morning, one in the afternoon, walking between them where possible.
It's also one of the few places where the free stuff competes with the paid: the parks, the bridges, the markets and the sheer density of good cheap food. Budget for two or three splurges, not eight.
Comfortable walking weather, long evenings, outdoor tables everywhere, and the parks at their best.
A workable shape rather than a schedule to obey — two fixed things a day, and room to change your mind.
Subway with a tapped card — no need to buy anything in advance. Walk between anything within twenty blocks. Avoid taxis in Midtown at rush hour; the train is genuinely faster.
New York is where budget mismatches hurt most: a $95 tasting menu and a $4 slice are both authentic experiences. Agree in advance which meals are group splurges and leave the rest optional so nobody's quietly overspending.