Caribbean, island by island.
The Caribbean works best when the brief starts with the way you want to use the week, not with a list of islands. A social St Barths stay, quiet anchorages in the British Virgin Islands and a longer southbound Grenadines itinerary ask for different yachts, embarkation points and air connections.
Choose the island group before the itinerary
“Caribbean” is too broad to be a useful yacht brief. St Barths and Anguilla produce a different week from the Virgin Islands, while the Grenadines reward a more linear cruising plan. We narrow the geography first, then source yachts that are genuinely positioned for it.
The aircraft and yacht should meet cleanly
The nearest runway is not automatically the best arrival point. Passenger count, baggage, aircraft performance, customs, operating hours and the yacht’s embarkation location can make a larger regional gateway and a short onward transfer the cleaner choice.
Holiday weeks need earlier decisions
Christmas and New Year compress yacht availability, berths, restaurants and aviation at the same time. Outside the peak holiday period there is usually more room to shape the brief around the actual guests rather than around what remains.
Leave room for weather
Trade winds, swell and anchorage conditions matter. A useful itinerary establishes priorities and preferred stops without making every day immovable. The captain retains responsibility for navigation and safe operation.