Hmmm, just my opinions but...
Must dos -
Baths (assuming you've never been)
Bubbly pool
Beautiful remote spots-
We usually eat dinner ashore, so don't got to the really remote spots, but a quieter spot we like is Great Harbor, Peter Island. There's one tiny restaurants (Oceans 7 - radio in when you grab your ball for a reservation) and they close around 9 so you don't worry about noise.
Best snorkels - Indians & Rhone
Don't miss -
Lobster dinner on the beach in Anegada (assuming you are comfortable going out there-) We like Wonky Dog but heard good things about a few of the restaurants there.
Agree with eating on the boat being a super value - we like to do this at Cooper Island beach club because it's a great spot and the food is kind of pricy (good, but pricy.) You need to get there by 1pm to get a ball because it's popular, but they only have 30 so it's never feels busy. They have a great beach and you can snorkel at cistern point. They have a dive shop for those that want to schedule a dive, an ice cream shop, and rum bar. And the bay is calm for people that just like to swim off the back of the boat.
Anything else -
Always have a "plan B" if your anticipated spot might run out of moorings.
Don't go out to Anegada unless you are comfortable with the distance, approach, and anchoring.
Don't expect wifi or credit card machines to always work.
Relax - you can't preplan this itinerary, so don't try to
