A small Cycladic island is the least forgiving destination on this list for the wrong shoe, and that is the thing worth deciding first. Paros, Antiparos and Hydra are stone steps, marble worn slick by a few hundred years of foot traffic, and lanes at an angle, so a sandal you have not walked a mile in will decide how much of the trip you actually see. Early September is still properly hot, and the meltemi wind will take a wide brim hat off your head and into the sea. Pack breathable linen, two swimsuits in blue that double as tops, and a tote big enough for a boat day. Dinner is relaxed but people do change, and a long linen dress with a low heel is the entire evening. Everything below was in stock this week, much of it on sale, with delivery landing before the weekend. One more thing about a small island: there is no shop to rescue you. Whatever you forget stays forgotten until you are back on a bigger island, so the list below is deliberately short and each piece does more than one job.

Work from the shoe up. A truly flat nappa leather sandal is the single purchase that makes the trip walkable, and it still looks intentional at lunch. Above it, a blue and white gingham midi, which is the piece you will wear three of four days. The swim is where the colour lives. Take two, one saturated blue and one blue with white trim, both cut high enough to carry you into town as a bodysuit, because changing on a small island usually means walking back to the room. For the hat, choose something structured with a frayed edge that survives being crushed in a duffel and does not fly off on a boat. Then the bags, and three is not excessive here: raffia for town, a second woven bag that zips for the boat, and a plain canvas tote for everything wet. On sizing, the gingham is cut long and belted, so check the length against a flat sandal. One more note on the bags. Buy the ones you would not mind ruining, because salt water, sun cream and a boat deck reach them in the first afternoon.

This is the one edit where we would happily spend nothing on the evening look. A linen maxi and a pair of statement earrings is all a taverna asks for, and the cream kitten heel is a want rather than a need. The flat sandal is the opposite: it is the one piece in the day combo we would tell you to buy first, because a blister on the second morning costs you the trip. We would also not add a wide brim hat. One is lovely and photographs beautifully and in that wind you will spend the evening retrieving it from the sea. Watch the stock levels, since several of these sale pieces were down to one or two units when we looked. If you take one thing away, break in the sandals at home this week, before they go anywhere near a marble step. We would also skip a second pair of shoes entirely. Two sandals, one flat and one low heel, covers every hour of this trip, and anything more is weight you carry up a hill.