When to go, and what you give up either way.
Every destination has a month that is quietly better than the one everyone books, and a month that is quietly worse. These pages say which, and why — the crowd, the heat, the festival that doubles the prices — because that is the part that actually decides an itinerary.
Europe5
- France
Paris
Dense enough that the walking distances decide your day. The month you pick changes the queues more than it changes the weather.
Read the guide - Italy
Rome
A city you cover on foot, in a climate that will decide how much of it you actually see. August is a genuinely bad idea.
Read the guide - Catalonia, Spain
Barcelona
A grid you can read at a glance and an old town you cannot. Two very different walking problems in the same city.
Read the guide - Czechia
Prague
Small, walkable and disproportionately crowded in its centre. The months you choose change the city more than in most European capitals.
Read the guide - Basque Country, Spain
Bilbao
A compact, walkable city that rewards two to three days — and one of the few places where a rainy forecast should genuinely change your plan.
Read the guide
Asia6
- Kantō, Japan
Tokyo
A city with no centre, built around railway stations. Plan by station, not by district, and the whole thing becomes manageable.
Read the guide - Kansai, Japan
Kyoto
The city where a badly ordered itinerary costs you hours. Spread out, seasonal, and worth planning properly rather than improvising.
Read the guide - Hokkaidō, Japan
Sapporo
A grid city that is quick to cover and works best as the start of something bigger. The season changes the trip more than in almost any other Japanese city.
Read the guide - Thailand
Bangkok
Traffic makes distance meaningless here. Plan along the river and the elevated rail lines, or lose hours to a two-kilometre journey.
Read the guide - Singapore
Singapore
Small, efficient and equatorial. The weather barely changes all year, which makes it one of the few cities where the month is not the main decision.
Read the guide - Türkiye
Istanbul
A city split across two continents by water, where the ferry is both transport and the best thing you will do all day.
Read the guide
North America4
- New York, United States
New York
A grid that makes distances legible and then punishes you for underestimating them. Twenty blocks looks like nothing and is a mile.
Read the guide - Mexico
Mexico City
Enormous, high-altitude and much easier than its reputation. The rainy season here is an afternoon, not a season.
Read the guide - British Columbia, Canada
Vancouver
A compact city wedged between mountains and ocean, with the sharpest wet-season contrast of any major North American city.
Read the guide - Quintana Roo, Mexico
Cancún
A beach destination where the month decides almost everything — including whether the beach looks like the photographs.
Read the guide
South America4
- Argentina
Buenos Aires
A European-feeling grid with South American hours. The evening starts far later than most visitors plan for.
Read the guide - Brazil
Rio de Janeiro
A city built around mountains and beaches, where the weather decides the day and the viewpoints are worth waiting for a clear one.
Read the guide - Peru
Cusco
The altitude and the dry season decide this trip. Both are worth planning around properly, and neither is negotiable.
Read the guide - Colombia
Cartagena
A small walled city on the Caribbean where the humidity, not the temperature, decides how much of the day you can spend outside.
Read the guide
Africa4
- Morocco
Marrakesh
A medina where a map stops helping and the summer heat is not a matter of preference. Spring and autumn are a different city.
Read the guide - Egypt
Cairo
Enormous, hot and slower to cross than any map suggests. The winter months are not merely nicer — they make the sites possible.
Read the guide - South Africa
Cape Town
A city arranged around a mountain and dominated by the wind. Keep the mountain day flexible and the whole trip improves.
Read the guide - Kenya
Nairobi
Mostly a gateway, and a good one. The month you pick decides the safari far more than it decides the city.
Read the guide
Oceania4
- New South Wales, Australia
Sydney
A harbour city where the public ferries double as the best sightseeing you can do. Plan around the water, not the roads.
Read the guide - Victoria, Australia
Melbourne
A grid city with the best coffee and the least predictable weather in Australia. Four seasons in a day is a local joke and an accurate one.
Read the guide - Otago, New Zealand
Queenstown
Two destinations sharing a name: a summer hiking base and a winter ski town. Pick the wrong season and you get neither.
Read the guide - New Zealand
Auckland
A city spread between two harbours, where the best days involve a ferry out of it. Two days in town, then the islands.
Read the guide
The list grows slowly because each page is written and checked by hand rather than generated. No prices, walking times or exact temperatures are published here: those come from the app, which builds them from open data at the moment you plan, instead of from a page written once and left to go stale. Where a date moves each year — cherry blossom, Ramadan, Carnival — the range is given and the fact that it moves is said out loud.