I'm just looking for some general advice on when, where, who, how, etc. (I know the WHY!) It'll be my wife and myself (our first bareboat, at least on a sailboat) and probably two other couples with no real sailing experience.

My initial thoughts for an easy, enjoyable experience are to hit the BVI during the spring. I've considered one of the flotillas, but I'm afraid that might cramp my style. I'd just like some opinions from others on what they would recommend as far as bareboating.

Also, for a March, April, or May '07 charter in the BVI, how far in advance do I need to book to guarantee I get what I want?

I suggest using a charter broker. No cost to you and they know the boats and the companies, can answer your questions, and help you find what you want. Ed Hamilton & Co is long-established and provides excellent service. (See http://www.ed-hamilton.com/).

Note: I am in no way affiliated with Ed Hamilton & Co.

If you want to venture a bit further West (Belize) then let me know.

Curtis Collins
www.nauticalventures.biz
www.belize-sailing-charters.com

One thing to consider if you are chartering with non-sailing couples, is that you will being doing all of the work. We have chartered with both sailing and non sailing poeple. If your wife sails that's a plus. Non-sailing people try to help, but usually tend to get in the way.
The BVI at that time of year is a great choice for 1st time charterers. If you are coming down from the Northeast, avoid school vacation weeks if you can. Flights are booked months in advance.
Flotillas are an option, but as you said, they may cramp you plans.
I would also suggest going with a 1st tier charter company like the Moorings or Sunsail.Both are full service companies, flights, hotels, etc.The Moorings, more so in my opinion. You will pay a bit more, but it is worth the expense.
Good Luck!