I recently bought a whole bunch of Riedel O wineglasses from Amazon ($17.99 for a box of 2, but if you look around, you can normally find a $25 coupon if you spend $125 in Home and Garden). So what is so special about a wineglass? Well, Riedel makes some of the finest wineglasses around; many high-end restaurants will not serve their wine in anything but Riedel crystal. The O series glasses are a twist on the traditional design in that there is no stem on the glass, rather they are wine tumblers.
The interesting thing about the O design is that the glass becomes a conversation piece. Furthermore, it adds a trendiness to drinking wine that does not necessarily come from drinking from the traditional stemmed glass; many of the wine bars that are popping up tend to favor wine tumblers to add to their general atmosphere.
Many people that I know tend to find wine drinking and especially wine selection a little intimidating. My suggestion on the perfect gift set would be 2 sets of O cabernet tumblers (about $35) and a bottle of a Beaulieu Vineyards Coastal Cabernet (around $12, but you can usually find it on sale for $8-$9). If you are looking to impress someone and spend a little more, substitute a bottle of Beaulieu Vineyards Georges De LaTour Cabernet 1997 (this could run you $100-$115; I have seen the 2000 on sale at Costco for $60, but it is a little young and 1997 was a spectacular year). Of course, you can always substitute white wine glasses and wines as you see fit.
One piece of advice: don't buy wine based on price; the most expensive is not always the best and may have a more complicated taste profile that some folks may not enjoy.