Unfortunately we may be 5 but we pack heavy so if we chartered with Island Birds it would need to be the 9 seater. We like going to STT and would probably take a water taxi if we might be late. We always build an extra hotel day on the front end of the charter so we can decompress before the start. We are pretty eager to get to the BVI from the moment we get off the plane. The problem is that we're using Delta miles which limits the number of options to get from Houston to STT on the same day.
Good to hear about Silver which may well be our option if we go through SJU. The couple of times, many years ago, we did the SJU to EIS leg on Cape Air were amazing but they've priced themselves out of consideration.
Thanks for all the advice. We'll figure it out in a couple of months when flight schedules for next July are published. This will be our 15th charter. In all cases to me planning the trip increased the excitement and anticipation of getting back there.