New Orleans
The most distinctive city in America, and the easiest to plan badly.
World-class food, walkable neighbourhoods, and prices that still feel like a mistake.
Mexico City has become the default answer for 'somewhere amazing that doesn't cost a fortune,' and it earns it. The food runs from street-corner tacos al pastor to some of the best restaurants on the continent, the museums are genuinely great, and the leafy neighbourhoods of Roma and Condesa are as pleasant to walk as anywhere in Europe.
At 2,240 metres, the altitude is the thing nobody warns you about. Plan a slow first day, drink more water than feels necessary, and go easy on the mezcal until day two.
Dry season means clear afternoons instead of the daily downpour, and spring brings jacaranda blooms across the whole city.
A workable shape rather than a schedule to obey — two fixed things a day, and room to change your mind.
Uber and Didi are inexpensive and the sane default. The metro is fast and very cheap but crowded; Ecobici works well in Roma and Condesa. Don't hail street taxis.
This is one of the best group cities anywhere — big tables are normal, Xochimilco is built for a crowd, and costs are low enough that budget mismatches stop mattering. Keep a shared list of everyone's saved taquerías; you will not remember the names.