Katharine Brasserie & Bar

Graylyn Estate is a genuinely beautiful place to have dinner, but the wine list is an afterthought in a room that deserves intention. Order the sea bass, grab the La Crema, and try not to think too hard about what this list could have been.

Sixty Vines is a solid, reliable wine stop in Winston-Salem — the by-the-glass breadth is real and the staff knows their stuff, but the list reads like a greatest hits album rather than anything adventurous. Come for the volume, stay for the pizza, but don't expect to have your mind changed about wine.

Oh' Calcutta's wine list is unremarkable on its own — but Tuesday nights flip the script entirely, and a $19 Pinot Noir with lamb vindaloo is a genuinely good time. Come for the food, plan around Tuesday, and don't overthink it.

Cin Cin isn't a wine destination, and it doesn't pretend to be — but Wednesday half-price wine all day on bottles and glasses turns a generic list into a genuinely good deal with a burger in hand. Show up any other night of the week and order a beer.

Quanto Basta punches above its weight for a mid-size Southern city Italian spot — the Italian-focused list is thoughtful, the prices are fair, and Thursday half-price bottles make it one of the best weekly wine deals in Winston-Salem. Come hungry, come on a Thursday, and order the Falanghina.

Umi is a fun hibachi night out, and the wine pricing is honestly fairer than it has any right to be — but the list itself is an afterthought, and no amount of fair markup fixes a selection that's two bottles deep in personality. Order sake, or a cocktail, and come back to us when they add a Grüner Veltliner.