Scott,
Try to time your arrival for the daylight hours. While St. Thomas itself is very well lighted along the north shore, the outlying islands are not. DO NOT DEPEND ON GPS readings when you try to thread through the outlying islands, unless you can SEE THEM.
Pillsbury Sound is preferable, because it's a nice run, good scenery, protected water, and is to windward of Charlotte Amalie. Once you get into the Sound (preferable through the Middle Passage), there are no navigational hazards except Current Cut (between St. Thomas and Great St. James Islands...go either side) and Cow and Calf Rocks off the end of St. Thomas...well marked on the charts and usually awash.
The Virgin Passage is quite a bit to leeward of Charlotte Amalie and other destinations on St. Thomas. If the wind is blowing (typical tradewind conditions), you don't want to do any more windward work in a 30-footer than you have to; it can be damned rough and wet.
Chart number 25640, Puerto Rico and the Virgin Islands, picks up at 19N...plenty of room north of the islands. Before that, use plotting sheets such as this one:
http://www.efalk.org/Navigation/plot1.html
to keep a DR plot.
Happy sailing,
Bill