Thanks for your trip report. I felt like I was reading a page out of my life. We've mostly chartered sailboats through the VIs and have spent many nights on the anchor at the bays you mention. During low (read: hurricane) season, starting beginning of August, you can sometimes get a room at the Ritz for as little as $150 or so a night. BTW, the best beaches and the best rum drinks in the VIs are on Anegada at the Big Bamboo.