If you start from Nanny Cay/Road Town/Hodges Creek here's an itinerary that will get the discussion ball rolling
Day 1 - provision, checkout, etc. so you won't get going until later. Head across the channel to Norman Island and the Bight. Dinner ashore at Pirates and drinks at Willie T (or both food & drink at Willie T's).
Day 2 - if late start, snorkel Pelicans; if early start head to the Baths on Virgin Gorda. Grab a mooring ball or anchor
at either Trellis Bay or Marina Cay. Dinner at Loose Mongoose/Last Resort or Pusser's.
Day 3 - snorkeling in the Dogs and then up to the North Sound - either Saba, Bitter End or Leverick Bay.
Day 4 - downwind sail to Sandy Cay for sunning/snorkeling. Choice of anchoring in Great Harbour on JVD with drinks @ soggy dollar, Corsair's or Foxy's OR head into Cane Garden Bay to moor and listen to Quito at night.
Day 5 - Head around the West End / Soper's Hole and motorsail home. Optionally, night 4 could be spent in Soper's Hole to make that final trip shorter.