I only did it once, almost 30 years ago, as a chaperone/skipper with a bunch of prep school kids on spring break, with three 42' boats out of Charlotte Amalie in St. Thomas.
So we did the much-travelled Francis Drake channel, out to the Bitter End in Virgin Gorda and back, over about 9 days. It's perfect for first-time charterers, as you have plenty of easterly tradewind, but relatively sheltered water between St. Thomas, St. John, Tortola, Virgin Gorda, and the islands just south of them.
I suppose it's more crowded now.
I was a New Englander then, stocked up with all the charts beforehand, got the Cruising Guide out of the library, only to find the chart they gave you on board was a glorified plastic placemat (and used as such), with anchorages shown in magic marker. Surprise! With the clear water, fair weather, and eyesight navigation, the placemat was all I needed.
And yes, we did get through it, with 19 high school kids, and 5 "adults" in their 20s, with no injuries, no arrests, no mishaps. What an excellent time. I went into it thinking it'd be a great trip if we didn't have the kids, but in the end it was more fun with them.
I've digressed. But try the "big four" islands above, you can't go wrong, unless they've become more crowded than I saw them in March of 1977 (which is likely).