If it were me, I would keep the boat you got which works well for you there, and I would fly to Tortola and charter for two weeks, split the boat costs with another couple of people.
I second 2Gringos opinion. I am considering the same thing. We have a Catalina 22 in Wisconsin. I am thinking of selling the C22 and getting a small/fun boat I can keep for free hoisted in my garage (Laser or whatever). Then spending the mooring fees saved on a yearly charter to warm places. Then you could sell the big towing truck and get a little Prius... unless you plan on stopping