The Caribbean season

The Mediterranean week is about the coast: harbours, towns, lunches, a beach club at three. The Caribbean week is about the water. The boat moves less, anchors more, and the day is organised around swimming, which is why families who have done both tend to prefer the winter one and say so quietly.

The three cruising grounds

The Virgin Islands

The easiest sailing in the world: line of sight navigation, short hops, reliable trade winds and dozens of anchorages within an hour of each other. The reason the bareboat industry was invented here, and still the right answer for a first charter, a family with young children or a group with mixed sea legs.

Saint Martin, Anguilla, Saint Barths

The glamorous end. Saint Barths at New Year is the single densest gathering of large yachts anywhere on earth, with a harbour that takes very few of them and an anchorage full of the rest. Expensive, social, and genuinely beautiful once the first week of January has passed.

Antigua to the Grenadines

The serious cruising. Longer passages between islands, open water crossings that are properly exposed, Dominica and the Tobago Cays and Bequia at the end. This is where sailing yachts go, and where the week feels like a voyage rather than a tour.

What is different from the Mediterranean

Provisioning is harder and more expensive, because most of it arrives by ship. Marinas are fewer and smaller, so the fleet anchors, which most guests prefer once they realise the tender is the taxi. Distances between good anchorages are short but the passages between island groups are open ocean, and a chop on the beam for four hours is a different experience from the Gulf of Saint Tropez.

And the gratuity convention is higher: fifteen to twenty per cent rather than ten to fifteen.

The New Year question

Saint Barths for New Year is a genuine spectacle and a genuinely poor value week: minimum stays, premium rates, a crowded anchorage, a town that cannot absorb the number of people who arrive, and a fireworks display watched from three hundred yachts at once. It is worth doing once. The same boat in the Grenadines two weeks later costs forty per cent less and gives you empty anchorages.