Here are some thoughts regarding a gift for a wine lover. If he is really into wine, he probably already has Riedel glasses (usually one of your first purchases), but he may not have a decanter. I love this Riedel decanter. Since it is a magnum size, it has room to swirl (to aerate young reds). It is also a good value and easy to pour from. Do not get one with the massive, flat bottom. They are a nightmare to pour from. Here is an Amazon link (on sale, plus free shipping).
http://www.amazon.com/exec/obidos/tg/de ... n&n=507846
I have a great leather wine bag, which I use for BYO's and Ravinia. It is the equivalent of a Coach bag for wine. It comes with a removable, chillable insert. I always receive compliments on it, and since it is pricey, he may not splurge himself (I also received mine as a gift).
http://store.mulhollandbrothers.com/esc ... &pls4=null
Speaking of BYO's, the Riedel 'O' series glasses are great for this purpose. No stem to break (or draw attention in a storefront BYO) and they come in a small box. Bed, Bath, & Beyond has them for $19.99 and they have 20% coupons floating around.
A Chateau Laguiole corkscrew is a handmade, lifetime corkscrew, which works great. No comparison to a cheap waiters friend corkscrew. I have a couple, but this one is my favorite.
http://www.amazon.com/exec/obidos/tg/de ... n&n=284507
You can always add some nice wine to round up to your desired price. Instead of throwing all of your money into one really expensive bottle, you can get many great bottles (with some advice and look for small production wines) in the $30 to $60 range. If he is a red drinker look for regions such as the Rhone (France), Priorat (Spain), Veneto for Amarone (Italy). For domestic choices try Oregon Pinot Noir, Sonoma Russian River Valley or Sonoma Coast Pinot Noir, Mendocino Pinot Noir, Washington State Cabernet blends or Syrah, and some California Syrah.
Good luck,
Al