Give serious thought to taking some sailing courses and/or charters in the Bahamas
and BVI. During the course work search out and ask the same question of the cruisers (not charterers) you meet.
The answer to your question has more to do with the way you live life than which boat is "best." Best for whom. Look at our boat. We find her perfectly suited for our style. I have also spent a week captaining a couple on their 50 footer which they worried to be too small. (They needed private cabins and heads. Lifestyle)
Sail to Barbados
direct from Newport
and then enjoy a long reach home via the Lesser Antillies, Bahamas
, and USEC. Skip the thorny path?
33: one of the prettiest boats of its size ever designed. Sail well too. IMHO!!