The trip you and your friends keep postponing

Every group of friends has it: the trip that lives permanently in the chat. We should really do this. Next year, definitely. It survives marriages, children, moves to other cities — always intended, never taken.

It is usually the women keeping it alive, and usually the women, eventually, who make it happen. What stops them is rarely desire. It is logistics — the impossibility of one person planning something that pleases six, and the fear of the trip not living up to all those years of postponing it.

Why a boat solves it

A gulet through the Cyclades removes the friction that kills these trips. There is no debate each morning about where to go or where to eat — the boat moves while you sleep, and you wake in a new anchorage. No one is the unpaid trip leader. The hotel comes with you.

You wake up in a different anchorage every morning. By day three, everyone has stopped looking at their phones.

— Ronak Jain

Days are for swimming off the back of the boat and reading in the sun. Evenings are long dinners watching the light go, on deck or ashore on Naxos. Santorini’s caldera at dawn, before the crowds, becomes the photograph none of you will stop sending.

The trip you have been postponing for years takes eight days. The only hard part, it turns out, was deciding to stop postponing it.