Well, consider this--- I was part of a crew, on a Frers 44, that left North Sound, Virgin Gorda ( at first light) for a check in by Noon at Red Hook Charlotte Amalie USVI.

It was before the < clear in at Cruz> but never the less, we still had time for a last swim at Christmas Cove. We were not late for check -in.

It is your vacation, do it the way you want. Yes, Leinster to North Sound is a long day, but you won't find North Sound a shut-out for either mooring or Anchorage. Anegada will be no problem. I'll leave the ear worm in your head that you'd EASILY be able to make check -in St Thomas from Jost on Day 7, which cleverly gives you room in your itinerary for " adjustment".