Jeff,
I like your tentative itinerary, we have done similar with our adult children. I think the typical charter guests start their sail on the weekend and progress in a CCW path around Tortola. Heading off in the opposite direction (CW) would generally mean fewer boats in the mooring fields for you. May is not a particularly busy time, I think you will find ample mooring locations provided you arrive before 2:00 regardless if you travel CCW or CW. The downside of going CW is the upwind slog on the North side of Tortola. One of our favorite sails is the downwind CCW sail from Leverick to Scrub. We come around the North side of Scrub and enter the pass between Great Camanoe and Scrub, sailing from Leverick to JVD around the North of G. Camanoe and Guana would be a very nice relaxing sail.
I think I would focus on where do you want to be for specific events (Full Moon Party, Michael Beans Show or Friday BBQ at Leverick, Wednesday North Beach party at Scrub, etc)
Cheers,
Tony
BTW We lived in Pine Book S/D in CLC years ago.
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