Bowlinglady: I have sailed twice with Windstar and I am their biggest fan, however I would NOT recommend Windstar to you if you will be travelling with a teen, as he will probably be the ONLY person his age onboard.
Windstar is voted every year as the world's most romantic cruise line, and is geared more towards intimate couples. They offer all watersports, but have no shows or entertainment, the kind you're used to on the big ships.
You could fit their entire casino in your living room, and the pool is about 10' X 10'.
I have absolutely NOTHING negative to say about Windstar, only very fond memories of the 2 best cruises I've ever experienced (out of 23 cruises total) On my 2 Windstar cruises, they took me to my favorite place on the planet - St. Bart's. I'm really looking forward to my next Windstar cruise, but I think Windstar would not be appropriate for your situation.
Like you, I've been on most of the major lines, last month was my first HollandAmerica cruise (westerdam) and I will NEVER cruise with anyone else but HollandAmerica (on big ships, anyway.) They are so much better than the other cruise lines IMHO.
Hope this helps you decide.