The First Trip of Retirement
He retired on a Friday in March, after 31 years at the same firm. On Monday his wife called us and said the sentence we have heard from almost every new retiree: we finally have the time, and we have no idea how to spend it.
The answer to 40 years of two-week vacations is not a two-week vacation. We built them a month in Japan with no alarm set anywhere in it.
The luxury of the slow month
Working travel compresses: fly in, see it, fly out. Retirement travel finally permits the opposite. Their month held only four hotels. A week in Tokyo with standing dinner reservations and empty afternoons. 10 days across Kyoto and a ryokan in the hills, where the second week is when the innkeeper starts cooking for you rather than for guests. A slow train south. A last week with nothing booked at all, which they spent going back to the places that had surprised them.
The trip cost less per day than their old compressed vacations. Time, it turns out, is the cheapest upgrade in travel.
Rain on the engawa
The photograph she sent us afterward was not a temple or a skyline. It was two cups of tea on a wooden veranda in the rain. Nothing was scheduled that day. That was the point of all of it.
One trip or several
The plain answer to the biggest retirement question: take the long one first, while the knees and the momentum are best, then shift to shoulder-season trips the working world cannot take. Winter in Lapland under the aurora, the vineyard harvests of September, safari in low season with the crowds gone. The calendar is finally yours; spend it where everyone else cannot.
You spent a career earning the right to stop rushing. The first trip of retirement should be the proof.
Carl Hill Jr
Good questions
How long should a retirement trip be?
Three weeks to a month for the first one. Long enough that the trip stops feeling like a vacation and starts feeling like the new life.
Should we do one big trip or several smaller ones?
Both, in that order: one landmark journey in the first year, then two or three shoulder-season trips annually, when prices drop and crowds leave.

