The choice of departure will have varying points of view. I have been chartering in the Islands for 25 years and leave exclusively now from STT and CYOA. Since I live in a Delta hub, connections are easy thru Atlanta. The provisioning is cheaper in STT. We usually spend 9-10 nights on board and since we are retired, it is"the trip" not the destination that is important. We like the anchorages around St. John and usually spend at least 2-3 nights in them. We have found we can easily sleep aboard and be either at Jost or Sopers if we wanted to be agressive. We love Christmas Cove for a last night but also found we can stay in Lamshur and still make it back in time to fuel up and check out on the last day. The primary reason I would say that we charter out of STT is, we have a great relationship with CYOA and they have earned our loyalty.