Ha! you guys are awesome. Anegada is back on the table. After all the variations and considerations I find myself coming back to almost exactly the itinerary from Rush early on this thread ...

Day 0: Miami-STT-ferry-Nanny Cay (last second provisioning, sleep on boat)
Day 1: Norman (check-out sail day, docking/mooring practice, unknown start and finish time)
2: Norman (snorkel Caves and Indians, hike, Pirate's and/or Willy-T's)
3: Sail a long close reach to Leverick or Blunder Bay (Saba, Bitter end)
4: Another day/night in the North Sound - rent a car/taxi at Leverick for Baths hike/snorkel, Coco Maya, MadDog's, Hog Heaven, Nail Bay, etc.
5: Sail to Anegada (weather/wife/Horizon-approval dependent!) Rent moke/truck. Cow Wreck/Tipsy's. Lobster dinner at Wonky Dog.
6: Sail to Marina Cay - Consider docking at marina for a refresher day/night, or get a ball at Marina Cay and snorkel Diamond Reef.
7***. Motor to Monkey point for a snorkel. Quiet night at White Bay Guana Island. Or Go to Cane Garden Bay.
8. Go to Diamond Cay/Little Jost (Sandy Spit, Bubbly Pool, Foxy's Taboo, B-line)
9. Great Harbor. Spend day at White Bay (Soggy Dollar), dinner in Great Harbor
10. Early sail back to base.

*** two cruise ships in RT day

Thinking Guana and Monkey Point should be impervious to the cruise ship crowds.

Variations:
Could move everything up a day if there is enough time to do the Day 2 Norman activities on Day 1.
Could Sail for Leverick on Day 2 and return to Norman on Day 9 for Indians etc and a shorter return to base on Day 10.
If Anegada is out, visit Eustatia/Oil Nut, spend another day in North Sound, or snorkel the Dogs and/or Sharkplaneo.

That's really packing it in huh!?! I'll be impressed if we get half of that list completed lol. So excited! Thanks for all the feedback!