Because nobody wants the restaurant staff staring at them while they
try to make a selection from the wine list then sneer at their choice.
Restaurants would love to sell more wine to their lunch and dinner guests. Many already have a bar selling wines by the glass. The problem is sticker shock at restaurant markups that has to be overcome. The other issue is a complicated wine list with no real info the the selections. So what can be done? In short find restaurants that are wine-friendly, where you can experiment a bit with different wines. Yes, it can be done without having 500 wines on the wine list. It should be fun and educational.
A wine list tailored to the food and clientele
This one is first because it should be the most obvious and should be done everywhere. Unfortunately, many restaurants lack the knowledge or the time to do this correctly and they let their distributor pick for them -- a really bad idea. If you've only got a few wines on your list then this is probably okay, but if you're a bit more serious about the wines served they figure out a way to have this done by someone that knows what they're doing and someone on the customer's and the restaurant's side (not the distributor's).
It's also knowing what's popular on the menu. It's pretty obvious if a restaurant sells lots of heavier food like steaks then you want heavier wines like Cabernet. If they sell lots of lighter fair then you want white wines. It gets trickier when one person orders steak and the other seafood. What is there on the wine list that satisfies both when they want to share a bottle of wine?
Another part of this is prices. A pizza joint doesn't need a hundred dollar Bordeaux on the list. Wine prices should be in line with food prices and your expectations.
Wine flights
If a restaurant offers rotating white and a red wine flights it gives you a chance to experiment without too much of an investment. Hopefully, this will include popular wines from smaller wineries and some less-known wine varietals -- something "odd" like Barbera or Albarino. This is a great way to get introduced to a restaurant's wine offerings. In fact, it would be fun to be offered a flight, maybe to share, when you first sit down before you order your dinner wine.
Wine happy hour
A restaurant that rotates between different specials is great so you don't get bored with the same ol' Chardonnay. Maybe a rosé in the summer; maybe a sparkling during the holidays.
Wine & food parties
This can be dinner choices or a simple cheese and charcuterie plate with several of the wines on the list. Some restaurants will occasionally provide a themed wine flight with a little cheese. Or it could be a lamb special served with a half glass of two different wines. This is great education.
Dinner with local winemakers
If you're lucky enough to be near any wineries a winemaker's dinner can be a great thing to attend. This is where the person making the wine brings in several offerings and runs through them during a dinner with you. It can be a little pricey, but can be a great source of wine information. Pick the brain of the winemaker while you're there.
These dinners are common in the Napa/Sonoma area. If you plan on visiting a wine growing area see if there are any of these dinners going on during your stay.
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