Ask around here. You'll get lots of advice. I'll start...
First off, depending on where you are in Colorado, you might find a number of opportunities for sailing right there. As you might guess from my screen-name, I used to live in Denver. There is a very active sailing club at Cherry Creek. Up in the mountains, there is a sailing club at Lake Dillon. Both welcome newcomers.
As for the BVI, my wife and I have chartered a couple of times with Sunsail, located in Road Town. We can definitely recommend them. The BVI is a great place for chartering, because there is something for everyone (whether you want night life, or quiet solitude), the sailing is usually quite easy, and the navigation
is as dead simple as it gets.
For a specific itinerary in the BVI I would first ask what you are looking for. Do you want music
and night life, or just a quiet anchorage and a lonely beach? (My wife and I are more of the latter type, by the way.)