An entertaining way to sample several wines at one sitting is to organize a home winetasting. Here's a sensible and fun way to begin.
Invite a group of 5-10 interested friends willing to share the cost of the wines. Warn them not to wear perfume or aftershave, so everybody will be able to smell the wines. Smoking during the tasting should be discouraged, too.
Select a like group of wines to taste -- say, six different chardonnays from a single year, but from different regions (for example, within California or from different countries). This format will illustrate how local conditions or winemaking techniques can influence the personality of a grape variety. Or, alternatively, try six different white or red wines (such as Cabernet, Merlot, Zinfandel, Pinot Noir, Gamay, and Syrah) to discover their differences.
Set a table with a white tablecloth and six wine glasses at each setting. Before your guests arrive, brown-bag each wine and number the bags sequentially from 1-6. Pour each glass a third full with the appropriately numbered wine (bottle #1 into glass #1). This makes the tasting "blind": the tasters won't know which wines are in which glasses, and thus will not be influenced by favorite brands or labels.
Provide your guests with a tasting sheet listing the wines in the tasting, with room to write notes. This enables them to keep a record of their impressions, so they can later buy the wines they liked best. If you want, have the tasters rank the wines in order of preference and tabulate the results.
Encourage everyone to smell and taste the wines and jot down their impressions. Allow as much time as needed. Either let the tasters exchange impressions during the tasting, or ask them to wait until everyone's finished, so no one is influenced by someone else's opinions. When everyone's done, have a discussion about the wines.
Provide water and neutrally flavored crackers and/or cheese to help keep your guests' palates fresh during the tasting -- and to help soak up the alcohol. You should also provide spitoons so your guests needn't swallow everything they taste (an important consideration for those who must drive home).
If your group enjoys the tasting, schedule another one to try a different set of wines. Before you know it, you'll have your own wine-tasting club and will be well on your way to becoming a wine expert. Plus, members can pool resources to buy quantities of the wines they like best, at the discounted prices many stores offer for buying by the case.