The question we are asked after where is when: not when to travel, but when to start. The answer depends on the destination, the season and the size of the party, and it is worth getting right because the places we prefer are small. A camp with eight tents or a chalet that sleeps twelve does not have a waiting list; it has a calendar, and once a week is gone it is gone.
The twelve-month list
Christmas and New Year anywhere warm. February half term in the Alps. The Serengeti migration river crossings from July to September. Gorilla permits in Rwanda for peak months. The best Okavango camps in the dry season. Any villa or chalet for a full week in peak season. For these, twelve months is comfortable and nine is already a compromise on choice.
Six to nine months
Most safaris outside the migration peak, the Maldives and Sri Lanka in winter, Japan for the blossom or the autumn colour, Peru in the dry season, Iceland in summer. Internal flights and permits are usually open and the better rooms are still available. This is the window most of our journeys are planned in.
Three to six months
Shoulder seasons almost everywhere: Kenya and Tanzania in the green season, Botswana from November to April, the Alps in January and March, Italy and Greece in May and late September, Morocco and Oman through the winter. Prices are lower and choice is wide. Several of our favourite journeys were designed in this window precisely because the peak had passed.
If you have left it late
Tell us anyway. Cancellations happen, small camps sometimes hold a tent or two for late requests, and a destination you had not considered may be in season and quiet. What we will not do is fill a gap with a place we would not send our own families, or imply availability we have not confirmed. If the honest answer is that the party should travel a month later or somewhere else, we say so.
What booking early actually buys
Not a discount, usually. It buys the specific house rather than a house, the camp in the right part of the reserve, the ryokan with the private bath, the chalet on the piste rather than a shuttle ride from it, and flights that connect without a night in an airport hotel. Those are the details that decide how a trip feels, and they are the first things to go.
