We enjoy tasting menus: pay a flat price and let the kitchen make all the decisions. Who better to know what's good? I say, "Chef, you decide!"
With tasting menus, we'll frequently get a wine pairing.
Alinea (1723 N. Halsted) is considered by many one of the world's great restaurants. Some years ago, four of us had the grand tour menu and the premium wine pairings. It was expensive…and it was stupid. So much wine…so,so much, that by about mid-way through the meal, I was, let us say, not as focused as I would have liked to have been.
That started me thinking: why not just ask the sommelier to give both my wife and me a half-pour each of all the selections in one wine pairing?
This dining strategy has served us well.
At Elizabeth (4835 N. Western) a few months ago, I asked the sommelier if he'd be able to split the wine-pairing. He said "Sure."
A friend asked how much wine each person would receive if they went with the full pairing, and the sommelier replied "About a bottle each."
A bottle each! Sheesh!!
Our table of eight ended up getting four wine pairings, with split pours for every one of us, and that was actually more than enough. We saved some money, some dignity, and we drove home with greater safety.
Critically, we had sufficient sips of several fine wines that enhanced the meal without blunting the buds.
Of course, sommeliers no doubt have the right to deny this kind of splitting, but it's never happened to us, and heck, if they get snotty about it, we'd just order one pairing…and request an extra glass.