You can also charter an IP from here:
Island Yachts U.S. Virgin Islands - Charter Vacations
No affiliation, but we'll be giving them a try to escape New England weather.
We've owned 5 boats over the last 20+ years from full keel's to whale bottom center boarders. As others have stated, our advice would be to think about how you like to use your boat, then pick a design that matches the application.
We've also found that the ideal boat for us changed over time, depending on where we wanted to cruise, where we wanted to moor, how many people we wanted to cruise with, etc. Whatever you do, it's unlikely to be your last boat.
We've had 5 LAST boats so far