It's best if you pick a theme. You could try different varietals, say Merlot, Cabernet, Malbec, and Grenache and try to have everyone pick out which one is which. This is harder than you think. When we went to a tasting like this with 6 reds, only one person of 12 of us had even 3 correct! You could pick regions to compare: a French Merlot versus a Washington Merlot, for example.
I decided on a Malbecs around the world tasting. Now all I needed was the wine and the supplies.
For our tasting, I went to my local wine shop and had the owner Carol help me pick out the wines she thought best represented the different regions at slightly different price points. I went home with my wine and printed up my tasting sheets. First, I made a sheet describing a little of the history and the flavors typical of Malbec and then I made a sheet with the bottles listed randomly on it for our guests to write their notes and guesses on.
Next, I needed to clean about 20 wine glasses. I have found the stemless glasses from World Market/Cost Plus to be the best deal. I used to own fancy, stemmed Riedels. Uh, most of those are broken now--nice crystal is fragile and dangerous to use at large wine parties--and so I switched to the stemless. The only problem is that stemmed glasses can have little wine charms on them for people to keep track of their glass. The stemless was a problem with this until I discovered these bottle writing pens that write like a charm on glass and is easy to clean off.
While you are at the wine shop or the kitchen shop buying supplies, don't forget to get some cute cocktail napkins too.
Set up your notes and glasses and be sure to have lots of pens, crackers, and drinking water handy.
Now you're all set! Tell everyone to bring a potluck dish and if you get expensive wine like I did for this tasting, no one is ever offended if you ask them to bring $15 each to pay for the tasting. I poured a small taste out to each guest, one wine at a time and then let them sample them all again before doing the big reveal and then more samples after they know what they are tasting. Don't forget it's just for fun so no big deal if you can't figure out what you are doing!
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