I'd do it in the blink of an eye in my Catalina 36
MKII - once I'm retired.
The trick, no matter what boat, is to have the time to move when the weather's right and hang out when it's not. You will hear it said over and over on this forum and others - "You can't have a schedule". Follow this and you can take just about any boat thru the Caribbean
If you can't follow this, then it may be best to charter
a boat in the BVI.