There are several most excellent first stops out of stt. It's about two hours to Maho/Francis. Also about two hours to the south Shore of St john bays. The choice comes down to wind and wave direction. Both are very nice choices. We have also gone stt to west end if we're starting in the morning. That's about 2.5 hours. Then we go to Norman after clearing in.

Cost wise you will have to run all the numbers. No ferry costs and no hotel stay before and after on stt. But higher cruising fees. Cheaper and better provisioning. And IMHO better equipped boats on stt. Give it a try!