Where should this trip go?

Portugal's southern coast delivers the beach holiday reliably: cliff-backed sandy bays in the centre, long flat sand in the east, and a windy, surf-facing west. It is easy, well served and good value, and it is developed enough that where you stay matters more than when you go.

A short stretch of vertical Tyrrhenian coastline where towns are stacked onto cliffs above small pebble beaches. The scenery and the food are the reason to come; the single coast road, the stairs and the summer prices are the reasons people wish they had gone in May.

Amsterdam is a small, flat, water-bound city where the historic centre is both the attraction and the pressure point. Because the national rail network fans out from its main station, the real planning question is how much of the trip you spend in the canal ring at all.

Bali is a volcanic Hindu island whose south has been built out for visitors while its interior and eastern coasts remain agricultural and comparatively quiet. Road speeds, not distance, are what decide whether a two-region itinerary here is realistic.

Cape Town sits between a mountain and two coasts, and its weather changes what is possible day to day: the cable car stops in high wind, one beach is calm while another is unusable. That makes flexibility, not sequencing, the skill this destination asks for.

A flat, cycling city where the appeal is design, food and harbour life rather than monuments. It is expensive and its winters are dark, but few cities of its size are as easy to move around or as consistently good to eat in.

Greece's largest island is a 260-kilometre mountain ridge with a developed north coast, a hotter and harder-to-reach south, a high interior with its own winter, and a drier east. What separates one Crete trip from another is less the compass direction than what is reachable, and open, when you go.

Pale limestone towers above alpine valleys, with an unusually good mountain-hut network and a mixed Italian, Ladin and Austrian food culture. Summer walking and winter skiing are both first-rate; the awkward months are the ones between, when lifts and huts close.

Iceland is a road-trip country rather than a destination you base yourself in: one numbered ring road links the regions, highland routes open only when the road authority judges them passable, and inter-regional public transport is too thin to build a trip on. Season decides how much of the country you can reach at all.

Kyoto keeps its temple districts on the wooded slopes around a flat modern grid, and reaching them depends on buses rather than the small subway. That turns a visit here into a question of timing: early hours and quiet districts, or queues in the famous ones.

A hilly river city that works as a short break in almost any month, with a food scene that has outgrown its old reputation and beaches and hill towns within an hour by train. The trade-offs are the gradients, the tourist concentration in a few districts, and how loud the popular quarters are at night.

An Arctic archipelago where sharp peaks rise straight out of the sea beside fishing villages. The landscape is the entire product, and it is delivered by weather: the same week can give midnight sun and clear ridges or four days of rain and cloud.

A steep volcanic island where the appeal is walking, mountain scenery and mild air rather than lying on sand. Madeira has almost no natural beaches; what it has instead is a network of levada water-channel paths, cloud-level ridges above Funchal and a growing food scene in the capital.

The Maldives is a scatter of low coral islands where almost every stay is one island, one property and one reef. The trip is therefore chosen twice: once for the island, and once for the boat or seaplane that reaches it.

Mallorca holds a real city, a UNESCO-listed mountain range and two very different resort coasts inside one island a couple of hours across. The island people remember is decided almost entirely by which of those they book, and by whether they hire a car.

Rome stacks two thousand years of building on top of itself in a walkable centre, and its biggest sites now run on booked entry slots. That turns trip planning here into a question of how many fixed appointments a day you are willing to build a holiday around.

Santorini is a drowned volcano whose western edge is a cliff of stacked white villages and whose eastern side is a flat run of black volcanic sand. The famous view and the swimming are on opposite coasts, which is the whole planning problem, and demand pressure on the rim is the other half of it.

Sicily is large enough that its two halves function as separate destinations: Greek theatres, an active volcano and baroque towns in the east, Arab-Norman Palermo, temples and wilder coast in the west. The island rewards a plan built around distance rather than a list of highlights.

Tenerife is a volcanic island tall enough to make its own weather. The trade winds pile cloud on the northern slopes and leave the south dry, so two halves of one island behave like different destinations, and the crater plateau around Teide behaves like a third.

Tokyo is not one city but a chain of dense centres strung along rail lines, each with its own scale and mood. Because the trains do the organising, the question is not what to see but where to stand — and how many days of that intensity you actually want.