Did a similar route on our Saba 50 in June 2016. Winds were SE16-18 with 3-4' seas. Rounded Steele Point at 11:30 am, and were anchored at Setting Point by 4:30 pm. Did a couple long tacks along the way, but were still driven a few miles west of West End Pt and motored the last few miles to the entrance channel.

If winds are at least south of east, you might want to motor to north tip of Guana Island or Great Camanoe then try to sail from there.