The possible itineraries are numerous and depend very heavily upon what your goals are. If you want to eat out and drink out every evening then you'll have one type of routine, if you would prefer to anchor or moor away from the hoi polloi you'll have another.
Everything in the BVI is reachable within a day sail, even with a smaller boat and not using an engine. The furthest two anchorages from each other are from the West End (Soper's Hole) to Anegada at about 30NM. Anegada is the shallowest anchorage but even boat drawing over 7' can enter and anchor.
Most charters start in Road Town and the best first overnight is certainly The Bight on Norman island - a quick and easy sail across the channel, snorkeling at the Pelicans or Caves and a large mooring field with choice of Pirate's dinner ashore or the infamous Willy T's afloat.
After that the choice is whether to take the clockwise or counterclockwise route. Clockwise would have you head upwind on the north side of Tortola and you would be going against wind and bigger seas in open water - not a problem if the seas are down and the wind coming from the right angle. More common is the counterclockwise route, where you would beat upwind inside the protected Sir Francis Drake channel.
Going from the Bight you could stop at Peter and Salt Islands during the day and end up in the Cooper Island mooring field for the night (get in close to shore as the outer moorings can be subject to swell). Snorkel the point at Cooper, I found it the best snorkeling in the islands.
Then head from Cooper to The Baths (in season, try to get there early to snag a mooring ball) for some daytime fun. From there the main route bifurcates and you can either head to the North Sound for the evening or cut across back to Tortola and spend the night in Trellis Bay or Marina Cay (or for those with deep pockets and a wish to visit a marina, to the new Scrub Island facility).
The North Sounders can stay at or around Leverick Bay or go to the Bitter End and Saba Rock - the next day can be spent exploring the Sound and environs or heading north for Anegada.
The Trellis'ers can snorkel Monkey Point and then continue to either Cane Garden Bay or Jost van Dyke. Sandy Cay and Sandy Spit should always be on the agenda.
Note that holding in Great Harbour isn't great and they have recently installed just a few mooring balls. If you do anchor there, try to get there early when there are few boats and lots of room. Make very certain that your anchor is set and you'll be fine - many parts of GH have only a thin layer of sand and it is easy to drag but you'll know it right away.
The Anegada visitors usually head from there to Sandy Cay/Spit and JVD. Some charter companies still have restrictions regarding Anegada but these days there are veritable daily flotillas heading there and entering the channel, just follow someone with your draft or deeper at an appropriate distance and the channel suddenly becomes very easy to enter
Continuing from Cane Garden Bay or Great Harbour your next passage would be around the West End - you can moor there for the evening and party ashore or continue into the Sir Francis Drake Channel and back to The Bight for the last night before returning the charter boat the next morning.