The Caribbean. Fly in once, step aboard, and cruise the islands that are best reached by sea.

Most Caribbean plans that come apart do so because the aircraft was chosen before the destination was settled. The region has a handful of full-length international runways and a great many small fields that take turboprops and light aircraft only, and there is no way round that with a larger cheque. A sensible plan therefore starts with where you actually want to be, establishes what can land there, and then decides whether the trip is one flight, a flight and a short hop, or a flight and a boat.

In practice the region divides into three. There are the islands a long range jet reaches directly from Europe, of which Antigua, Barbados and Nassau are the obvious ones. There are the islands reached by a short second leg in a light aircraft or a turboprop, such as St Barths, Mustique and much of the Grenadines. And there are the places best reached on the water, where a yacht is not a luxury addition but the sensible form of transport, which is most of the British Virgin Islands and a good deal of the Bahamas.

London to the eastern Caribbean is roughly eight to nine hours. An ultra long range aircraft makes it comfortably nonstop with a full cabin; a long range type will usually do it too, depending on payload and winds; heavy jets often plan a technical stop, in the Azores or Bermuda, which adds an hour or so and is entirely routine. The honest version of this conversation happens at the enquiry stage, not after a quote has been accepted, and we would rather have it early. See ultra long range jets and heavy jets.

Settle at the same time whether the aircraft stays. In the festive fortnight, parking at the popular gateways is finite, and often the answer is that the aircraft drops you and repositions, returning for the departure. That is normal rather than a sign of a poor operator, and it needs to be in the plan rather than a surprise. See private jet charter and how charter works.

The British Virgin Islands are the clearest case. Short distances, protected water and dozens of anchorages within an afternoon of each other make a yacht the natural way to move rather than a treat added to a villa holiday. The same is true of much of the Bahamas, where the interesting islands are scattered and the water is shallow and beautiful, and of the Grenadines below St Vincent.

Elsewhere a yacht answers a different problem. In St Barths at New Year it solves the villa shortage and the traffic at once. Around Antigua it turns a single base into a week of different bays. We arrange charters, crews, berths and tender movements through operators and agents we know, and plan the flights and cars around them. See yacht charter, motor yachts and catamarans.

Everything described above is arranged: the aircraft, the yachts, the crews and the cars on the islands, all through operators we know and deal with regularly. The London end is ours. Our own chauffeur, in our own car, collects you at home and takes you to the private terminal at Luton, Farnborough, Biggin Hill or Stansted, and is there again when you land back, whatever the hour and whatever the flight has done in the meantime. One contact, one itinerary, and a plan that already includes what happens if something slips. See private jet transfers and meet and greet.