Woohoo, I found the 'wine-o' section!

I love it but it doesn't love me. Stains my teeth, makes me fat, poor and stoopid. Oh how I love it.
Q for you in the wine-know:
Would like to give a wine or spirits related wedding gift to a newly married colleague/friend. Does it make sense to sign them up for a 'subscription' for about 6 months or so? (my price range of $100-150 may make this bright idea completely unrealistic). I don't know which wine 'club' is better than another.
He's young, hip and an appreciator of the finer things in life - I'd like to hit that mark with gift. Oh, and I'm in AZ in case that makes a difference in shipping restrictions.
Thanks for any advice. Heck, if I find something great, I may as well sign myself up.
ANNE