The two weeks that decide a Caribbean year

One fortnight, most of the revenue

On the marquee Caribbean islands — St Barths above all, with Mustique and Harbour Island close behind — the fortnight spanning Christmas and New Year can account for a quarter or more of a house's annual take. Rates run at multiples of high season, minimum stays of ten to fourteen nights are standard, and the best houses are committed a year in advance, often to the same families.

That concentration has consequences everywhere else on the calendar. It is why January can be surprisingly available, why staffing is at its strongest in December and thinner in the shoulder, and why owners are relaxed about a soft October.

“One fortnight can carry a quarter of a house's year. Every other week on the calendar is priced in its shadow.”

Where the value sits

The first half of December is the clearest bargain in the region: identical weather, the season's staff already in place, and rates a fraction of what the same house commands three weeks later. Late April into early May is the mirror image — settled weather, the crowd gone, and houses willing to negotiate a long stay.

January after the first week is the quietly sensible month. High-season conditions, a fraction of the competition for tables and boats, and rates that have stepped down a full band from the holiday fortnight.

The hurricane question, answered plainly

The official season runs June to November, with the statistical peak from mid-August to early October. Many of the best houses close for part of it, and those that stay open price accordingly. Travelling in September is a genuine gamble; travelling in June is, for most islands, a modest one against a real discount.

The mitigations are practical rather than clever: book with a supplier whose cancellation terms are written down, take insurance that names named-storm cover explicitly, and assume the shoulder-season staffing is lighter than the brochure implies.

How to book the holiday fortnight, if you must

Eleven to twelve months out, with a flexible view of which house rather than which island, and an acceptance that the marquee properties recirculate rarely. Second-tier bays on the same island frequently deliver ninety per cent of the week at sixty per cent of the rate, and nobody on the terrace can tell the difference.

Or move the trip to the first week of December, which is our advice roughly nine times in ten, and spend the difference on the boat.

“Second-tier bays deliver ninety per cent of the week at sixty per cent of the rate, and nobody on the terrace can tell the difference.”