Twister, or some other simple long keeler under 30 foot. If you're somewhere as nice as the Carribean, who wants to spend all their time with their head burried in the engine room, trying to repair all those electrical systems that aren't really needed anyway?
(Translate as, I'm lazy, so the less there is that needs looking after, the happier I am)
Much depends on crew availability, but I have more or less decided on a Westerly Conway. Heavy strong, not too wide down below, loads of cupboards, you would call them lockers, which would stay shut in rough weather, two heads, two bedrooms, sorry, cabins, while there is plenty of room in the saloon to stow bedding when guests come to stay. And very affordable. If I won the lottery, I would have an HR 42, or Najad, or maybe a Malo of the same size. But I don't do the lottery, so that is unlikely. I don't much like the trend for wide yachts, they seem to be so stable upside down. And expensive; and bouncy in a seaway.