"Somewhere warm, not too touristy" is a wish, not a plan — and it's where most vacations quietly go wrong. This week turns that fuzzy wish into a scored shortlist of real destinations, each one checked against the budget and dates you locked down in Week 1 instead of against a pretty photo. Three prompts take you there at three depths: a plain-English shortlist you can run cold, a weighted version that ranks candidates on the factors you actually care about, and a full destination dossier matrix you can defend to whoever you're travelling with. By the end you'll be able to answer "where should we go?" with a reason, not a shrug.

"Somewhere warm, not too touristy" is a wish, not a plan — and it's where most vacations quietly go wrong. This week turns that fuzzy wish into a scored shortlist of real destinations, each one checked against the budget and dates you locked down in Week 1 instead of against a pretty photo. Three prompts take you there at three depths: a plain-English shortlist you can run cold, a weighted version that ranks candidates on the factors you actually care about, and a full destination dossier matrix you can defend to whoever you're travelling with. By the end you'll be able to answer "where should we go?" with a reason, not a shrug.

This week’s divergence teaches a vital lesson about using AI for high-stakes decisions: AI is a terrible oracle, but an incredible filter. If you ask an AI "Where should I go?", it will feed you glossy, agreeable travel-brochure clichés. But if you force the AI to act as a strict logistical analyst—commanding it to score destinations on crowds, weather risks, and visa friction before it is allowed to praise them—it becomes an invaluable tool. The difference between a bad output and a great one is simply demanding that the AI show its math.

"Somewhere warm, not too touristy" is a wish, not a plan — and it's where most vacations quietly go wrong. This week turns that fuzzy wish into a scored shortlist of real destinations, each one checked against the budget and dates you locked down in Week 1 instead of against a pretty photo. Three prompts take you there at three depths: a plain-English shortlist you can run cold, a weighted version that ranks candidates on the factors you actually care about, and a full destination dossier matrix you can defend to whoever you're travelling with. By the end you'll be able to answer "where should we go?" with a reason, not a shrug.