Here are some tips, with some personal favorites:
1. Sailing the BVI is easy line-of-sight navigation with many anchorages and alternates, almost all of which have bars and restaurants ashore. They also have mooring balls for a nightly $30 fee and almost all have places to anchor. Any overnight sail would put you past the BVI in another nation, the longest sail from Great Harbour on Jost to Anegada or the tip of the North Sound is easily done in one sailing day.
2. Diamond Cay on Jost van Dyke. Protected in a north swell, with Foxy's Taboo ashore and walk to the bubbly pool. Many mooring balls, and a great new bar called the B-Line. Just a stone's throw from Sandy Cay and Sandy Spit. Quiet at night.
3. Cane Garden Bay. Only if there's no north swell, lots of mooring balls. Great live music with BBQ meal at The Elm twice a week.
4. North Sound, anchorage/moorings off the Sand Box on Prickly Pear. This is for that one night when you want to feel alone. Usually the moorings aren't taken and the Sand Box beach bar is only open during the day. Sunsets are nice and once it is dark the stars really come out, along with the lights above Leverick on Virgin Gorda.
5. North Sound, Leverick Bay. Great dockage rates and a unique happy hour show with Michael Beans most nights in season. This is in case you or your significant other want one night at a dock.
6. Cooper Island. Best when you get a mooring ball as close to the beach as possible and when there's no north swell. New restaurant with good food, and the best snorkeling in the BVI at cistern point. Also a good jumping-off point for a dash up to the Baths, which needs to be done early in order to get a mooring ball.
7. White Bay, Jost van Dyke. Only enter in settled conditions, but the beach and atmosphere are great, and the Soggy Dollar Bar is the home of the Painkiller.
8. Anegada. This is a different BVI. But it is relatively far out and only worthwhile when you have time to explore the island.
Provisioning can be done in several places, with more or less selection and the less selection you have the higher the prices. I'd get all beef/meats at the big supermarkets in Road Town as well as any non-standard or specialty items. Easy provisioning with dinghy access is at Soper's Hole (bring a winter coat for the grocery store, they cool the whole building down!), Great Harbour on Jost van Dyke, Spanish Town, Trellis Bay. Smaller store at Leverick Bay and if you feel like really spending your extra cash you can stock up at The Bitter End.