We sailed for a week last March - it is crowded. We found that most of the popular mooring spots filled up by about Noon. While the mooring fields were busy, we never really found overwhelming crowds (other than Soggy Dollar). But we ate dinners on board a lot during that trip.
Sounds like Leverick is definitely on your list - we loved it!
You'll get lots of advice from others here on anchorages and itineraries.
As for restaurants, we were just down last month and our two favorite meals were Wonky Dog on Anegada and Sugar Mill on Tortola. I think the Sugar Mill would be an easy taxi ride from Cane Garden Bay. If not the Sugar Mill, just south of Cane Garden Bay is Bananakeet - great food with a spectacular sunset view.
Have fun planning!
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