Guessing whether you will like a city from ones you already know: what actually predicts it

I loved one big city and bounced hard off another that everyone said was similar. After getting this wrong twice, the useful predictors turned out to be structural, not cultural.

Predicts well

• Whether you can live without a car. The single strongest one. Someone who loved a dense walkable city and disliked a sprawling one is not reacting to the culture, they are reacting to needing a car for a sandwich.
• Whether the good bits are concentrated or spread out. Concentrated cities reward wandering. Spread-out ones punish it, and if wandering is how you enjoy a place you will have a bad time.
• How much of life happens outdoors and in public. Cafes, squares, streets at night versus indoor and private.
• Time to the nearest thing that is not city. Matters far more than people expect for stays over about a week.

Predicts badly

• Population size. Two cities of the same size can be opposite on everything above.
• Reputation for being fun, friendly or beautiful. These are about visits, not living.
• Food scene, which is good almost everywhere now.

The trap
You are usually comparing a holiday to a stay. Ask what you actually did on the good trip: if the answer is walking around with no plan, that is a density question and it is answerable from a map before you book anything.