Reading about wine can be entertaining as well as edifying. But as with dancing, eating lobster and sex, by far the best way to learn is by doing.
The good news is that you get to do it with friends (the wine, not the sex). The better news is, you don't have to leave the comfort of your home, if you're willing to host a tasting party. This is easier to plan, prep and execute than a dinner party, and a swell winter warmer of an experience. A few suggestions:
Setting up: What size gathering? Depends entirely on what you and your abode find most comfortable.
Obviously, guest compatibility is a consideration, but it's not essential for all hands to have the same level of expertise; even among novices, it's OK to include a wine savant -- as long as he or she is not prone to flaunting it.
You don't have to have Riedel glasses, but something decent is essential for swirling and sniffing; it's perfectly fine to ask your friends to bring their own. Take precautions against the inevitable spillage from overly enthusiastic swishing or creeping klutziness.
Choosing the wines: Sticking with one grape is the optimum approach, but even then the options are endless. Pick a varietal and a price range, then find examples from different countries or regions. Or have everyone bring their favorite under-$15 red blend.
One strategy: Compare a white Burgundy (2005 "village" wines in the $15 range are drinking nicely), an unoaked chardonnay from Australia (McWilliam's, Grant Burge) and another from the United States (Callaway, Tolosa), and a prototypical buttery, oaky California offering (Estancia, J. Lohr).
Some interesting variations: Check out different levels of dryness-to-sweetness for wines that run that gamut, such as riesling, Vouvray, gewürztraminer or sparkling wines. Or take a "relative" approach: zinfandel with its Italian cousin, primitivo; or syrah/shiraz with its offspring, petite sirah.
